Chapter 6

Nomenclature

C C

C C

C C

C F

C Cl

C Br

C I

O

HO

C OH

C N

C N

C N

C CO

C SH

C CS

H

H

H

Alkane

Alkene

Alkyne

Cycloalkane

Halide

Phenyl

Carboxylic Acid

Alcohol

Ether

Amine

Thioether

Thiol

Alcohol Nomenclature

OH

1) Find the longest carbon chain containing the alcohol

2) Start numbering from the end closest to the alcohol

3) Finish with -ol as the suffix (takes priority over -ene & -yne)

2-pentanolhydroxyl group

HO

Alcohol Nomenclature

1,2-ethanediol

ethylene glycol

OH

OH OHHO OH

1,2,3-propanetriol

glycerine

Amine Nomenclature

1) Name all of the substituents coming off the nitrgoen (ignore hydrogens)

2) Place them in alphabetical order add a space then amine

methylpropyl amine

NH

Best way to name amines until the structures become too complicated

Alternative Amine Nomenclature

1) Find the longest carbon chain containing the amine

2) Start numbering from the end closest to the amine

3) Finish with -amine as the suffix (does NOT take priority over -ol, -ene, or -yne)

2-pentanamineamino group

NH2

N

Amine Nomenclature

NH2

NH

N

N+

primary amine

secondary amine

tertiary amine

ammonium ion

Figure 6.29

NH2R

NHR2

NR3

N+R4

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N

O

OHO

NH

OH OH

F

Lipitor

O

ON

S

Cl

Plavix

OH

NH

O

OH

OH

Advair (Salmeterol)

Ether Nomenclature

1) Name both substituents coming off the oxygen

2) Place them in alphabetical order add a space then ether

methylpropyl ether

O

O CH3 OCH3

OCH3

methoxy group ethoxy group propoxy group

Thiol Nomenclature

1) Find the longest carbon chain containing the thiol

2) Start numbering from the end closest to the thiol

3) Name normally then add thiol to the end

2-pentanethiolmercapto groupSH

HS

SS

disulfide

Thioether Nomenclature

1) Name both substituents coming off the sulfur

2) Place them in alphabetical order add a space then sulfide

methylpropyl sulfide

S

Solvents in Organic Chemistry

Adapted from: Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; New York: Harper & Row, 1987.

Solvation

H

Br

H Br

H

Br

Acid-Base Properties of Alcohols

R O H R OB B

R OH

H

pKa pKa

R = H

R = CH3

R = CH2CH3

R = C(CH3)3

-1.74 15.7

-2.2

-1.9

-2.6

15.5

15.9

17

Acid-Base Properties of Amines

NRR

R

NRR

R

HH

Amine pKa

NH3

CH3NH2

(CH3)2NH

(CH3)3N

9.24

10.63

10.78

9.80

Activation of Alkyl Halides

R X

Mg 2 Li

R Mg X R Li + LiX

Mg Cl + MeOH H + HO Mg X

Li + HH H + LiH

N

R

RR

N

R

RR

N

R

RR

Nitrogen Inversion

NCH2CH2CH3H3C

H3CH2C

Nitrogen Inversion

NCH2CH2CH3H3C

H3CH2C

H

N

R

RR

N

R

RR

H H