Organic Chemistry

Section 24.6 Intramolecular Reactions 1011

Table 24.2 Relative Rates of an Intermolecular Reaction and Five Intramolecular Reactions

Reaction Relative reaction rate

A 1.0

B

C

D

E

F 5 * 107 M

CBrO

O

O

O

C O− + −O Br

O O

O

O

1 * 107 M

O

O

O

H CBr

H

O

O

+ −O Br

C O−

O

2.2* 105 M

CBrO

O

O

+ −O Br

C O−

O

O

O

R=iso-C 3 H 7

1.3* 106 M

R=CH 3

2.3* 104 M

O

O

O

CBr

O

O

+ −O Br

C O−

O

R

R

R

R

1 * 103 M

O

O

O

CBr

O

O

+ −O Br

C O−

O

Br ++CH 3 C O CCH 3 Br

O O

CH 3 CO−−O

O

CH 3 C O

O

related to the calculated probability of forming the conformation in which the car-
boxylate ion is in position to attack the carbonyl carbon.

four carbon–carbon

bonds can rotate

three carbon–carbon

bonds can rotate

O

CO

O

CO−

Br

O

CO

O

CO−

Br