Advices For Studying Organic Chemistry

H C OH

C 6 H 13

CH (^3)
C H
C 6 H 13
CH 3
HO
(R)-(–)-2-Octanol (S)-(+)-2-Octanol

[]α^25 D = –9.90° [α]^25 D = +9.90°

1) The (R)-(–)-2-bromooctane reacts with sodium hydroxide to afford only

(S)-(+)-2-octanol.

2) SN2 reactions always lead to inversion of configuration.

The Stereochemistry of an SN2 Reaction

SN2 Reaction takes place with complete inversion of configuration:

HO − HOδ− HO

An inversion of configuration

C Br

HC 6 H 13

CH 3

δ+ δ− δ− C

CH

6 H 13

CH 3

C Br + Br−

H 3 C

HC 6 H 13

(R)-(–)-2-Bromooctane (S)-(+)-2-Octanol

[]α^25 D = –34.25° [α]^25 D = +9.90°

Enantiomeric purity = 100% Enantiomeric purity = 100%

6.10 THE REACTION OF TERT-BUTYL CHLORIDE WITH

HYDROXIDE ION: AN SN 1 REACTION

1. When tert-butyl chloride with sodium hydroxide in a mixture of water and acetone,
   the rate of formation of tert-butyl alcohol is dependent on the concentration of
   tert-butyl chloride, but is independent of the concentration of hydroxide ion.