Organic Chemistry Video 1

Organic chemist ry is the chemist ry of O / X f ^ s O O ,

OCc.cV£><^ is the pr inciple a tom.

This is the chemist ry of biological nature , bo th cur rent l y l iving and

g n C g , l iv ing.

Not all ca rbon conta in ing molecules are organic. Two examples are:

1. co^ 2. C K i "

Organic chemist ry can also be called hydrocarbon chemist ry because it focuses on carbon atoms bonded to V ^ -< c< r - ' f ' j i,-- ."^ .

Nomenclature = Naming System

CjHc e t h a n e

H H H-C-C-H

I I H H

or CH3-CH3

Formula

St ructura l Formula

Condensed Structura l Formula

Line Diagram

Organic Chemistry Video 2- Aliphatics ALKANES- Saturated hydrocarbons Nomenclature (Naming Rules)- end with "-ane" General Formula

CnH2n+2

„ , 1 - Molecular U Carbons prefix „ , Name tormina 1 Meth CH4 rre-VVccrvG 2 Bth Cdlf , «>V'.-<rcr.€ 3 Prop C H s ^ ' "^^ '- '-^ 4 But C,,ll|o b v ' > t"^'^'^' 5 Pciita CMIi;, ^ e r s V A ^ e

6 Hcxa C,,H,., Vx ev.A

7 llept C7H,,, . C f ' <rvOC 8 Oct CsH,8 T'CAift r-.£. 9 Non C H , , , rs^f^^,-^C^

10 Deca Cioil22 d C C i l A e -The first 3 alkanes have no isomers (they can only be drawn I way).

H H H H H H I I I I I I H-C-H H-C-C-H H-C-C-C-H I 1 1 I I I H H H H H H

Isomers o f Butane C4H10

Rule •;1-Nanie the longest ciintinaoiis chain oreaihiin atoms (uitii group), and end it with -ane.

H H H H

H-c-'|-c-c-H t j U ^ f c j ^ s C H H H H

Kale ^2- Keiiiaining side chains will be given rhe eiidiiiii -yl

Organic Chemistry Video 3

L\c\u: corrnii'ii;-.!--Hydrocarbons in which the 2 ends o f the chain are attached at the ends to form a ring

The rule for naming is they al! start with "cyclo-".

Name the carbon ri im. Start it with "c>clo".

CjH,,

C,l!s

OH, 1,3- dimethylcyclopentane

Halides-

Sometimes an organic compound will contain one or more halogen atoms.

Name the compound by using a prefix form for the halogen: fiuoro, bromo, iodo, chloro.

Note which carbon has the halide if there is more than one C.

H 1 H—C—F

I fluoromethane

CI I

H-C-CI

CI ;:i i:::l H

H' ' H H >

C H 3

H3C I 2.- vOC D > C

Organic Clnemistry Video 7

Isomers o f Pentane C5H12

H H H H H

• • t i l H H H H H

H n F T H

H I

H - C - H H I H H I I 1 1

H - c — c — e - c - H • I • I H H H H

Rule •-'3- Mulliple side chains w ill nsc prctixcs 2 is di-. 1 is tn-. 4 is leira- and so on,

H - c — c — C - H H-[C—=^C-—-C>H p r o ^ \ c \H I H H A H H - C - H H - ^ H

I • , , , H H y., , , \

Isomers o f Hexane C(,H]i

H H H H H H

1 1 ) 1 1 1 H H H H H H

H I

H-C-H H I H H H ^ -^cAWJt \b^^Vr ,r^G

H-c C--C-C-C-H H H H H H

H I

H-C-

H V H - C - H

C c—C — C — H ' t " i I I

H H H H H

l\(ilc r- 4- \ l]ic hwi^st number liii,.iMi)n ID)- L-ai.il skic L-li;an it lhc)-e is annllier possible locaaon u

localfd Ciu baek and ti\e last 1 I S U I I K T S

H ^ H-C-H

H i H H I i I I

H-C — C — C - C - H \ X\' H ' H H

H-C-H I

2 12 "i^*^^-'^ i \ ^> fsC

Isomers o f Heptane C-H

H H H H H H H I • I I I I I

H - c - c - c - c - c - c - c - H K ^ ^ ^ ^ r s O H H H H H H H

I I • I • I ^

H H H H H H

H

H - c - c ^ c — c - c - c - H I I I I I I H H H H H H

H H-C-H

H I H H H I I I I I

H

2 'I ^w.'+^t.^p^.''^••^ A / i C

H I

H-C-H H H I H H I

3, ?> -c^"-.'r^£^-*A,,.,: p^y^-'

C-C-H \ I I 3 1

H H I H H H - r - H

Video 5 Alkenes

Rule #1-Name the longest chain w i th the double bond. It is not always the longest chain o f carbons. End it w i th "-ene".

C2H4i C-C ,v

Rule ^2-When necessary use the lowest number to give the location o f double bond ' the longest chain.

C4H8

C4H8

H H H I

c^c-C-C-H b t ^Vev^e 14^ I I

H H

H H H H t • • •

H H

H H H H I I I I

iCsHioj J , / I I I

H H H pen-* f'f-\t^

H H H H H I I I • I

H - C - C = C - C - C - H I I I H H H

H - C - H ' H J H

; C = C - C - C - H ; l-rr^ \ W U C W A C 3 Hi H H

H

H - C - H H H I I

X-C- C-C-H I I H H

H

H - C - H

I V C = C - C - H

H ^ I • I H

H - C - H I

H

,'i • (y- fry•^•'^'.fi^

Video 6 Alkynes

Alkynes- Are •W'\( \ WaA / 'A (not all single bonds) hydrocarbons (hydrogen and carbon only) containing 1 carbon to carbon triple bond ''C^C".

The rule for naming is they all end with "-yne".

The general formula is CnH2n-2, n is the number of carbons is used to determine the number of hydrogen atoms. Example n=5, so H-(2(5)-2)=8

Rule #1 -Name the longest chain w i th the triple bond. It is not always the longest chain o f carbons. End it w i th "-yne".

ic^H:' H - C S C - H

i H C3H4i H - C i C - C - H

H

Rule #2-When necessary use the lowest number to give the location o f triple bond in the longest chain.

,cm4 H - C S C - C - H

H H C4H, : H - C i ^ C - C - H | b u A l A n € ,

I t H H

C4H6

H H

H H H

C^HJ H - C E C - C - C - C - H l i t

H H H

c,ih\-c-CSC-C-C-H ! H H H

• i-' r C

Naming Dienes

Dienes- Organic compound containing 2 separate carbon to carbon double bonds C=C

The rule for naming is they all end with "-diene".

The general formula is CnH2n-2 , n is the number of carbons is used to determine the number of hydrogen atoms. Example n=4, so H=(2(4)-2)-6

Dienes are I SOMERS of" Allcynes (same general fo rmula )

Naming Compounds- Aga in , ignore all the hydrogen's. We only wo r r y about carbon atoms.

Rule #1 -Name the longest chain that contains both double bonds. End it w i t h "diene".

Rule #2-When necessary use the lowest numbers to give the locations o f both double bonds.

C 4 H 6

; 1,3-butadienc i

1,3-pentadiene

iCsHg 1,4-pentadiene

H . H

.H H H I H H

H-C-C — C: C C-H

H-C-H

H H - C - H , H - C - H , . . 1 ! ,

H H I I H J, t V ' T f V ^ C X ' A - ^ 4 \

H I H H H H-C-H , , ,

\iu\c "5- When ihcrc are 2 tliriereiu side chains name llieiii in alphabclical order using the carbon prefix (mclh. clh

H\ 1 H H ^ ^ ^ r-'=^< '•'' '•Cx H\ I H H I 1 I I I I

\"'t1| 'i 'l v.W' I H H H

H-C-H ,

Organic Chemistry Video 8

The rule for naming is they all end with "benzene".

The general formula is C„H2n-6, n is the number o f carbons is used to determine the number o f hydrogen atoms. Exaniple n=c: so i l=(2(8)-6)=10

Kiilc I-Name the benzene ring. i-Jid il wi lh "ben/cnc".

Rule -2-\\''hen nccess;ir>' use the lowest iiinnhcr to c llie loctiUons of side chains that CDiiie olTlhc hcn/.cnc.

H

A A V V V

o

o

CH-CHXH..

(.•..II; • O

O i l i. l lO_

P.

Organic Cliemistry Video 9 A l c o h o l s - a i t Lompounds in which one or more h}driigeii atoms in an alkane h;i\ been replaced b> ;i l iydro.wl (-(.)! I) group.

Ol 1- i.s hydiuxide. but in otganic chemisliy side chains end with -o\

R-OH

Types o f Alcohols Monoh\'drox\',\lcohols-contains I -Oi l group

1 I I

- C - O H - C - C - C -- C -

1 I I

- c - - c

Primary Secondary Tertiary s ' ' < , Ihc jt-OI i is auachcd til one olher carbon (oil the end)

ihc (.•-( ) i l is atlachcri to two other carbons

• the (.•-()! I is attached to llirce otiua carhiiiis

!'rimar\c

^ V ^ P^V p. A.A H - . : - c - c - O H T '

I I I H H H

Sccoiiilarv

I H O H \

H-C-C-C-H I i I H H H

H H H H

rliai'N r'.xami

X H O H t I I

H - C - C - C - H H I H

H - C - H

2.- rr-,<>'^'Z f^f^C

Organic Chemistry Video 10 Carboxylic Acids

Organic Acids- An organic acid is an organic Q compound wi t l i acidic properties. The most common 11 organic acids are the carboxylic acids whose acidity is R— associated with their carboxyl group -COOH. OH

N'.''! 1KMIL l i i i i.;i'-,_-carbo.\_\e acids ha\ an -i)ic acid suf'h.x (c.u. (icladccanoic acid)

Name Expanded Structure

0

Cr> * ^i'- (• Ail 0

H c - O H H - C ' ^

H H O I I II

H - C — C — C — O H

( o i K l c n s s \ S l i a i c l L i r c

CH : ,CX )O l i CH-,C11:C( ) ( )H

'0 {*<;<v\ ,v,t i \ r " " t

V r:' .

Organic Chemistry Video 11 Esters Nornenc laT ' j re Esters (R-CO-O-R') are named as alkyl derivatives of

carboxylic acids. The alkyl (R ' tg roup is named first O (the carbon chain from the alcohol). The R-CO-0 part

p ^ is then named as a separate word based on the

\ Q _ [ ^ carboxylic acid name, with the ending changed f r o m -

oic acid to "-oate".

I S i ' ii, A '• U )\-is the geiiertil name lor a chemical rcifCtion in which two chemicals (iNpicalK an ttcid and an alcohol) lorpt'tin ester ;is the

y/f-:V('''*' J retiction p)-odiicl (water). •

, S'•- nl !'C:-.i'--When a c;irbo.\ylic acid and an alcohol read. ;i water molecule . ^ \ ' \ ' ' IS removed, and an ester molecule is Iprmetl,

R - < . ' - O H + H - ' : » R R - ' •-<:iR - + H j C )

H H , - - 0 - C - C - C - H ' \ ' ' / I I I

^ ' H H

H H H H ,;—U — C - C - H I t . / I t

H - C - c ' H H I I

H H

O H H II I I

H c - O - C - C - H H - c ' H H

Organic Chemistry Video 12 Aldehyde/Ketone/Ether/Amine

o II c

Aldehydes-A compound with a carbon atom which i IS 11 bonded to a hydrogen atom and double-bonded to an oxygen atom. This

is found on the end of the chain, ketones have this carbon in the middle \o H either).

W Mornenclature-The name is formed by changing the suffix -e of the

IJdrent alkane to-al , so that HCHO IS named methanal, and 0 I CH^CH^CH.CHO is named butanal. ) i ^'^r€('Mkx}pC.

r . x n a n d e d ^, ,. , , ! • U -SlrL ic ture N a i r i e r x p a i u l c u S i r u c l L i i ' c N a m e

H O H l-l ^ H l-l I I

H-C-C-C-H

Ketones- A compound with a carbonyl group (()""C,') linked to two other carbon alcaiis in ihc cheniicai compound. The C'"-"() is roiinii some\\hcre m the middle ol' Ihe chain (iiol the end). I liree carbons arc needed to form ;i ketone.

XviiViCilClilturC- changing the sul'Ilx -e of ihc ptirem alkane to "-one"

o

Name Expanded Structures

V n V H-C-C-C-H

I I H H

H O H H I II I I

H-C—C—C-C-H I I I H H H

H O H H H I II I I •

H - C - C - C - C - C - H I I I I H H H H

Name Condensed Structures

Cll-.COCH-,

Cll-,C()CH,Cli : ,

' c ' l i i C ' o c i h c r h C t i ^

i CHjt.'IhCOCHzCH, 1

CI-l;C()CHiCHiCHiCll, 4 _ J

f»v-

\ i I C i ' S - a chemica l compound where and D _ Q _ D oxygen atom connects two subst i tuted groups i 2

\ *l 1 i c ; iCMl '.ifC-lilhers can be nanicil b\g each ot'lhe Ivvo carbon groups as a separale wwd tolliMved b\ space and the word elher.

Name Expanded Structure H H

^ . fTNC-W-s'^ H - C - O - v - H

n H H • I )

H - c — 0 - c - t - H

H H H H • I I I

, . . H - C - C - O - C - C - H

e-i'Vs .\r '^^PK. r CH3-CH2-0-CH,-CH2-CH3 ' j r ' ; J ; CHJ-CHS-CHO-O-CHS-CHJ-CHJ

\mines-ln amines^ the hydrogen a toms m the ammon ia have been replaced one at a t ime by hydrocarbon groups. On this page, we are only looking | at cases where the hydrocarbon groups are s imple alkyl g roups

I R

H

N-C-H H N-C-H

H H

Petroleum Reactions

Fractional Distillation- I he \s compuiieiils of crude oil have dir ie icm sizes, weighls and boiling leiiiperalures; so. the first step is to separate these components. Because thcv have dilfereni boiling temperatures. the_\n he se|iarated easily by a iiroccss called fractional distillation,

Dl'itlllatiOfi oi Cnicie Oil

-I Hydiocarboris with 1 10 4 c i rbon atoms

mm i i l

Hytif i.<.;iibcns, with

I Hydi DC^ifbons with " I 13 10 16 ca i lx in atoms

—J Hvdi r.r.nibons with "\^ i^: c.-trlion Jiomf,

H /'.il ucnfboi'i:^ v^ith [iic-re rhan

20 carbon iitonis

T y p e s o f P o l y m e r s :

1 ) A d d i t i o n P o l y m e r s - f o r m e d by a d d i t i a n p o i y m e n i d l r u n l e a c t i o n : t h e m o r o m e f ' s d o u b l e b o n d o p e n s , a l l o w i n g t h e m o n o m e r un i t s to j o i n e n d t o e n d . T h e n a m e o f t h e p o l y m e r is f o u n d by p u t t i n g a " p o l y " m f r o n t o f t h e m o n o m e r ' s n a m e F o r e x a m p l e , p r o p y l e n e m o n o m e r f o r m s p o l y p r o p y l e n e .

a ) P o l y v i n y l C h l o r i d e 1, F o r m e d f r o m V iny l C h l o r i d e m o n o m e r ( c h l o r o e t h a n e ) 2, T h e d o u b l e b o n d b r e a k s , a n d V C m o n o m e r un i t s j o i n e n d to e n d , 3, U s e d fo r w a t e r p i p e s , r e c o r d a l b u m s r a i n c o a t s , s h o w e r c u r t a i n s , w i r e i n s u l a t i o n , v i n y l s i d i n g

B H H H H H H H H H B H H 1

H 1

H 1

H 1

c = ^ c c - ^ c c — c t; = C C = C C = C C = r C = C 1 1 1 1 1 CI B O H n

I E

a i H

1 1 n H

1 CI

1 H

a B a H i V i n v l ct i lui id '? rnoriLin *1 = le i rorn e,ir h o tbe i

H H H H H H H H H H B E H 1

H t

n 1

B 1

.C — C • . C - C . C — c- c- c — c - C - c- . C C • c - C 1 1 1 1 1 CI B a H a

1 H

1 a

H 1 1 n H

1 0

1 B

o B o 1 E 2] A i:at,3ly:,t bieak 'F t l c i Joublp bi n d ; , i jpHninci iJf' a fr^e urif .air^d ,.alH'i

H E n H H U H H H H E H H B B H

H- C- C — C - C - ~ C - C - C - C — C — C - C - C - C — C - C - C — B I I I I I I I I I I 1 I I I I n B O H a H n H n H c i B a B a E

3) The v iny l ch lor ide [riuriMrrit^rs luiri end to end t h e re.^C-tion i:, t e i r n i r i a t ed by t h e additni i ' i i:if l i v d r r i f i e n g a s , •which a d d s on to Ihe end of the [ in lyv iny l c h i o i i d e i n o l e r i j l e , l i t opp ing any fu i t he i t i o l y i n e n z a t i o n .

b ) P o l y s t y r e n e

1 F o r m e d f r o m s t y r e n e m o n o m e r ( p h e n y l e t h a n e , b a s i c a l l y e t h e n e w i t h a b e n z e n e a t t a c h e d to it) 2, T h e d o u b l e b o n d b r e a k s , a n d s t y r e n e m o n o m e r u n i t s j o i n t o g e t h e r , 3, U s e d f o r p las t i c m o d e l k i t s , s t y r o f o a m

B H

li-)-- r — r I I r iU' i iber i : i f :=tyiene rnonorr iPr un i t ' i cc irnbine l o u i to fn-rri a cl ' ia'n of •;,v'ieiie rr ir-nrime.s n un i l s UMH.] y n i j ; t a r t w i t h I « K l ' t y i e i i e m o n u r n e i u n i t s , t l ie nolyrne- >'JII1 be 2 0 0 0 ijnir: . loi,,..

c ) P o l y t e t r a f U i o r o e t h e n e ( t e f l o n ) 1, F o r m e d f r o m t e t r a f l o u r o e t h e n e m o n o m e r 2 T h e d o u b l e b o n d b r e a k s , a n d T F E m o n o m e r un i t s j o i n t o g e t h e r 3, U s e d f o r no-s t i ck p a n s 4 . A c c i d e n t a l l y d i s c o v e r e d in 1 9 3 8 by R o y P l u n k e t t ,

r F I I C = C -I I F F

••• F F , I I I i,

H - f - C - C - f - E 'i I I ; \ f I I

n riun' ibyr ot 11-b rnonn ine r un i t s Lor i ib i r io luLjett-ie- to fo i i r t s obiain c i tTFE rnoriorni?! n un i ts long If-.'Ou z:ian •,'Vitli 1500 TFE n i n n o m e r u n i l ? , ihe p o l y i r i e ' w i l l tie 1500 un i t s lont j

© 2 0 1 1 , M a r k R o s e n g a r t e n

2 ) C o n d e n s a t i o n P o l y m e r s - formed by dehydrat ion synthesis of difuncl ional monomer units H and OH are removed f rom the ends of the m o n o m e r units, allov^ing them to jo in toge the i Water is given off as a byoroduct.

P o l y e s t e r

1, F o r m e d f r o m m o n o m e r un i t s tha t h a v e an a l c o h o l f u n c t i o n a l g r o u p on o n e e n d and a c a r b o x y l i c ac id f u n c t i o n a l g r o u p o n t h e o t h e r e n d , 2- T h e o p p o s i n g e n d s u n d e r g o d e h y d r a t i o n s y n t h e s i s , a n d f o r m t h e p o l y m e r

0 a 0 H O B O II I I

HO - C - C OB * B D - C - C -OH I 1 H B

The iT ionomers above lo:,e H . i i id O H and bund •ngethe i I h i o u n h iJehy.i l i . it inn vnthe-,i::, t-o l o i m

H o - r - c — O H • H n - n — r — O H + n o - c —c—OH i 1 I H n H

/ e a e i B

watei IS i o ; : , bei;.suse only the H'-; i n j ' JH' ; b e l ' * o e n ibe i B U B O H O H Q

Uriel unit':.

B O - C - C — 0 - C — C - O - C - C - 0 - C - C - 0 - C - C—OH • 4 HjO I I I I

H H n H u

H O - C - C - O H H o l - c - r - 0 - 1 H I I

n I fljO lal tn ir i- i i j t i tul ll"ie tnirn,i1irir

3) Rubber a) cis- P o l y i s o p r e n e ( t i r es ) , p o l y b u t a d i e n e ( t i res ) p o l y c h l o r o p r o p e n e I f s l eoprene w/ire c o v e r i n g , a u t o m o t i v e d r i v e be l t s w e t s u i t i T a t e n a D ) , N i t r i l e ( a u t o i r o l i v e h o s e s a n d g a s k e t s )

1. F o r m e d by a d d i t i o n p o l y m e r i z a t i o n

2, T h e r e s u l t a n t m a c r o m o l e c u l e is t a c k y a n d not v e r y s t r o n g It g e n e r a l l y has a l o w m t i l t i n g po in t

3 In o rde r t o m a k e th is s tu f f s e r v i c e a b l e , it m u s t by t o u g h e n e d up . T ins is d o n e by a p r o c e s s w h e r e b y t h e p o l y m e r c h a i n s a re c r o s s - l i n k e d w i t h su l fu r . T h i s t o u g h e n s u p the r u b b e r . T h i s p r o c e s s w a s d i s c o v e r e d a c c i d e n t a l l y by C h a r l e s G o o d y e a r in 1 8 3 9 T h i s p r o c e s s is c a l l e d v u l c a n i z a t i o n . U n f o r t u n a t e l y , w h e n h e a l is a p p l i e d to r u b b e r so H e a l e d it d o e s i iOi m e l t b u l b u m s , r e l e a s i n g C O C O 2 a n d S O 2

S i S i

s s

i s

s i s s

Natu ra l [ : " : i lybutadiene l u b b e i the [ j u l yn i e i s t r a n d ; , are s e p j i a - e n o n i H,3fh other , r nak i ng the rubber E;nft and t a r | , y nut at at su i t ab le tcr t i res n i l i n s e s lOi be l t s

Tbe MM U I J , ,H-e un,...,,' , , s i l f i i ! ato, T in ; , u . i l

e.Ecn l i the , Thr;, ...•uli.ai 1,

e i i l i e i ie iy I j u g h mi d i i:'ei1ei:tly su i ted loi l u e

u b b e , I

and ut :l-ie I

© 2 0 1 1 , M a r k R o s e n g a r t e n