wade powerpoint/lecture for chapter 5

7252019 Wade PowerpointLecture for Chapter 5

httpslidepdfcomreaderfullwade-powerpointlecture-for-chapter-5 172

Chapter 5

Stereochemistrythe study of the 3-Dthe study of the 3-D

structure of moleculesstructure of molecules

Organic Chemistry 8th Edition

L G Wade Jr



Stereochemistry

bull For pharmaceuticals slight

differences in the 3D spatial

arrangement can make the difference

between targeted treatment and

undesired side-effects



ypes of somers

Structural or Constitutional sameformula different bonding se$uence

CH3CH3

CH3CH3

CH3

CH3

CH3CH2OHH3C-O-CH3

and

and

C amp (

C ) amp



ypes of somers

Stereoisomers same formulasame bonding se$uence but

different spatial arrangement of the

atoms +eometric or cis-trans

) nantiomers mirror image isomers

3 Diastereomers not mirror images ofeach other



Stereoisomersbull Same bonding se$uence

bull Different arrangement in space

bull ample ampC-CampCamp-Camp

has two geometric cis-trans0 isomers

OHOH

O

O

OHOH

H H

O O

fumaric acid mp )12C maleic acid mp 31C



dentify the following pairs as

either constitutional isomers

stereoisomers or identical

)

3

(

5



Chirality

bull 4ampandedness right glo6e doesn7t fit the left handbull 8irror-image ob9ect is different from

4 nonsuperimposable0 the original ob9ect



hich ob9ects are chiral



Chirality in 8olecules

bull he cis isomer is achiral ie not handed0bull he trans isomer is chiral

bull nantiomers nonsuperimposable mirrorimages different molecules



ampelpful 4rulelt

bull if both hal6es of a molecule are

symmetric about an 4internal

mirror plane then the molecule is

achiral



=rob 5-) Draw the mirror image of the original

structure gt determine whether the mirror image is

the same cmpd abel each structure as chiral

or achiral and label each pair of enantiomers

c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O

a cis-)-dimethylcyclobutane b trans-)-dimethylcyclobutane

e



Chiral Carbonsbull etrahedral carbons with ( different attached groups

are chiral bull f there7s only one chiral carbon in a molecule its

mirror image will be a different compound enantiomer0

bull Chiral carbons are designated with a



H Cl

CH3

OH

H

H

Sol6ed =rob 5- Star each

asymmetric carbon atom



=rob 5-3 Draw structures and star

asymmetric carbon atoms

a0 )-pentanol b0 3-pentanol c0 alinine

g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2



8irror =lanes of Symmetry

bull A molecule containing ) or more chiral carbons willbe achiral if the molecule has an 4internal mirror

plane of symmetry

bull A molecule with an internal mirror plane cannot be

chiral



=rob 5-5 Determine whether

each compound has an internal

mirror plane of symmetry

CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0



Baming nantiomersusing the Cahn-ngold-=relog con6ention

bull nantiomers are different moleculestherefore they must ha6e different

names

bull sually only one enantiomer will bebiologically acti6e

bull Configuration around the

chiral carbon is specifiedwith E0 or S0





Assigning =riorities

CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0

bull orking in 3-D rotate molecule so that lowest priority group faces away from you is behind theC 0

bull Draw an arrow from highest to lowest prioritygroup

bull Clockwise E0 Counterclockwise S0



he steering wheel analogylt

bull urn the steering wheel clockwiseand the car turns to the right E0



Sol6ed =rob 5-) Draw the

enantiomers of 3-dibromobutane

and label them as E0 or S0

H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4



Sol6ed =rob 5-3 he structure of one of the

enantiomers of car6one is shown below Find

the asymmetric carbon atom determine

whether it has the E0 or S0 configuration

car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front

bull Switch group ( with whate6er group is

pointed away from you Bow determine

configuration as normal he originalcompound is the new compound7s

enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror





Answer From Solutions

8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away



=roblem Are these pairs of

compounds enantiomers or

diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S





+ood and Had nantiomers

he errible Case of halidomide

bull A +erman drug company launched thalidomide

in I52bull t was found to act as a

bull analgesic bull tran$uiliGer bull antiemetic for treating morning sickness

bull Current knowledge held that drugs could not

pass the placental barrier and harm a fetusbull FDA ne6er appro6ed of use in the SA but

thalidomide came in from o6erseas and for use in

clinical trials











Eemember

bull E0 and S0 are names

nomenclature terms0

bull d0 and l0 or K0 and -0 are physical properties and must

be determined bymeasurement





Eacemic 8itures

bull $ual $uantities of d- and l- enantiomers

a 5J5J mi0

bull Botation dl0 or plusmn 0

bull Bo optical acti6ity

bull he miture may ha6e different bp and

mp from the enantiomers



Eacemic =roducts

f optically inacti6e reagents combineto form a chiral molecule a racemic

miture of enantiomers is formed



ptical =urity

bull Also called enantiomeric ecess

bull Amount of pure enantiomer in ecess ofthe racemic miture

bull f op 5JL then the obser6ed rotationwill be only 5JL of the rotation of the pure enantiomer

bull 8iture composition would be 25-)5



Chirality of Conformers

bull f e$uilibrium eists between two chiral

conformers molecule is not chiral

bull Mudge chirality by looking at the most

symmetrical conformer

bull Cycloheane can be considered to be

planar on a6erage



8obile Conformers

Bonsuperimposable mirror

images but e$ual energyand intercon6ertible

So consider it

planar on a6erage



ip earn to Draw Cylics in

=lanar 4Approimations

H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H





=rob 5-( Draw each compound in its most

symmetric conformation and determine

whether it is capable of showing optical acti6ity

c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH



Bonmobile Conformers

f the conformer is sterically hinderedit may eist as enantiomers

Allenes



Allenes

bull Chiral compounds with no chiral carbonbull Contains sp hybridiGed carbon with

ad9acent double bonds -CCC-

Allene is achiral

MAKE THE MODELS



Allenes ill He Chiral f heir

nd +roups Are Different





Draw the

carbon chain

6ertically

Fi h = 9 ti E l



Fischer =ro9ection Eules

bull Carbon chain is on the 6ertical linebull ampighest oidiGed carbon at top

bull Eotation of 1J deg

in plane doesn7t

change molecule




bull Do not rotate IJ deg

bull Do not turn o6er out of plane ie noflipping like a pancake

Fi h 8i



Fischer 8irror magesbull asy to draw easy to find enantiomers

easy to find internal mirror planes

bull ample )S3E0-)3-dibromobutane



Fischer E0 and S0

bull owest priority usually amp0 comes forwardso assignment rules are backwards

bull Clockwise -)-3 is S0 andcounterclockwise -)-3 is E0

bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H



ip Draw the Fischer=ro9ection and then

determine whether it is E0or S0 f it is not the one

you want 9ust switch the

horriGontal groups



=rob 5-2 Draw a Fischer

=ro9ection for each compound

CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol

b E0-)-bromobutan--ol

= b 5 1 8 k Fi h



=rob 5-1 8ake a Fischer

=ro9ection Draw the mirror

image Determine whether themirror image is the same as or

different from the original

H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c



=rob 5-I abel each asymmetric

carbon atom as E0 or S0 in each

Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f



bull Are cisOtrans isomers enantiomers or

diastereomers

Categories of somers



Diastereomers

bull Stereoisomers that are not mirror imagesbull +eometric isomers cis-trans0

bull 8olecules with ) or more chiral carbons



Diastereomer Alkenes

Cis-trans isomers are not mirrorimages so they are diastereomers

CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing

Compoundsbull Cis-trans isomers possible

bull 8ay also ha6e enantiomers

bull ample trans-)-dimethylcyclopentane

8 C d



8eso Compoundsbull An achiral compound containing two or

more chiral carbonsOchirality centers

bull Also contains an internal mirror plane of

symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f



wo Sets of nantiomers of

the Same Compound are

Diastereomers



=rob 5-)J For each pair gi6e



=rob 5 )J For each pair gi6e

the relationship between the

two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t



=roperties of Diastereomersbull Diastereomers ha6e different physical

properties mp bpbull hey can be separated easily by

distillation

crystalliGation

chromatography bull nantiomers differ only in reaction with other

chiral molecules and the direction in which polariGed light is rotated

bull nantiomers are difficult to separate

E l ti f ti



Eesolution of nantiomers

Eeact a racemic miture with a chiral compoundto form diastereomers which can be separated

Chromatographic Eesolution



C o atog ap c eso ut o

of nantiomers



nd of Chapter 5



Stereochemistry

bull For pharmaceuticals slight

differences in the 3D spatial

arrangement can make the difference

between targeted treatment and

undesired side-effects



ypes of somers


CH3CH3

CH3CH3

CH3

CH3

CH3CH2OHH3C-O-CH3

and

and

C amp (

C ) amp



ypes of somers












OHOH

O

O

OHOH

H H

O O







)

3

(

5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



ypes of somers


CH3CH3

CH3CH3

CH3

CH3

CH3CH2OHH3C-O-CH3

and

and

C amp (

C ) amp



ypes of somers












OHOH

O

O

OHOH

H H

O O







)

3

(

5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



ypes of somers












OHOH

O

O

OHOH

H H

O O







)

3

(

5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5







OHOH

O

O

OHOH

H H

O O







)

3

(

5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






)

3

(

5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Chirality













ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5











ampelpful 4rulelt




achiral







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5







c )-bromobutane



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



=rob 5-) Continued

CH3

H

H

CH3

CH3

CH3

H

H

O


e









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5









H Cl

CH3

OH

H

H








g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






g0 h0

CH3 CH3

OH

CH3 CH3

OH

CH3 OH

O

NH2





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





plane of symmetry


chiral






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






CH3

CH3CH3

h0

Bo

asymmetric

carbons

g0





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





names









CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






CH3

H

NH2

OHOCH3 Br

Br

CH2CH2Br

Br CH3

Halinine

1

2

3

4

3-dibromobutane

1

2

3

4



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Assigning E0 or S0













H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5










H2CH2C CH3

Br Br

HC

3-dibromobutane

CBr Br

CH3 H3C

HH

CH2CH2Br CH2CH2Br

1 1

2 2

3 3

4 4







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5







car6one

1

23

4

(E ) S0

O

C

CH2H3C

H

s it or



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



hat to do when

group ( is in front

bull Eotate the

molecule in

space so that

group (

points away

from you E

S0



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



hat to do when

group ( is in front

bull Draw the arrow

but then apply the

rule backwards

eg now clock-

wise is S and

counterclockwise

is E Elt S0



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



hat to do when

group ( is in front




enantiomer



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



ample Amphetamine

E0S0 E0

NH2

CH3

H

NH2

H

CH3

NH2

CH3 H

mirror






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






8anual to =rob 5-

Cl H

ClH

HCl

ClH

(d)

HH

ClCl

(e)

H H

ClCl

S0

S0

S0

E0

Assume lower groups

are back and away





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





diastereomers

CH3CH3

CH3

CH3

CH3 CH3

CH3

CH3

S

S

E E

CH3

CH3

OH

Cl

CH3Cl

OH

CH3

E E E S













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5













clinical trials











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5











Eemember


nomenclature terms0







Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





Eacemic 8itures


a 5J5J mi0







Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Eacemic =roducts





ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



ptical =urity













planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5









planar on a6erage



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



8obile Conformers



So consider it

planar on a6erage





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





H

H

HH

HH

H

HHH

H H

O

H

H

HH

HH

HH

H H

H

H

H

HH

H

H

H

H

H O

H

H

H

HH

H

H

H

H

H

H

H H

H

H

H

H

HH

H

H

H








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5








c )-dichloroproane

Br

H

H

Br

d cis-3-

dibromocycloheane

Br

H

H

Br

f trans-(-

dibromocycloheane

Cl

Cl

H3C H

HH





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





Allenes



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Allenes



Allene is achiral

MAKE THE MODELS









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5









Draw the

carbon chain

6ertically

Fi h = 9 ti E l






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






in plane doesn7t

change molecule






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






Fi h 8i








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5








Fischer E0 and S0



bull ample

(S )

(S)

Br

Br

CH3

CH3

H

H






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






horriGontal groups





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





CH3

OH

OH

CH3

Br

OH

a S0-propane-)-diol


= b 5 1 8 k Fi h







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5







H

CH2OH

CHO

OH

CH2OH

Br H

CH2OH

Br

CH2Br

Br

CH3

a b c





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





Fischer =ro9ection

H

H

CH2OH

CH2

OH

OH

OH

CH3

COOH

HH2N

d h i

Br

CH2OH

CH3

Cl

C i f




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5




diastereomers




Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Diastereomers







CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





CH3

H

CH3

H

CH3

CH3

H

H

Diastereomeric Eing



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5



Diastereomeric Eing




8 C d






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5






symmetry

H

H

CH2OH

CH2OH

OH

OH

S t f ti f





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





Diastereomers








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5








two compoundsCl

Cl

ande OHH

OHH

CH2OH

CHO

HHO

OHH

CH2OH

CHO

andf

Br Br

and

d

= ti f Di t





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5





distillation

crystalliGation




E l ti f ti









of nantiomers



nd of Chapter 5









of nantiomers



nd of Chapter 5



nd of Chapter 5

wade powerpoint/lecture for chapter 5

Documents