Organic Chemistry

(The same substitution product would have been obtained if the reaction had been an

reaction.)

d.

Because a high concentration of a good nucleophile is employed, we can predict that

the reaction is an reaction. Therefore, the product will have the inverted configura-

tion relative to the configuration of the reactant. But since the configuration of the reac-

tant is not indicated, we do not know the configuration of the product.

e.

Because a poor nucleophile is employed, we can predict that the reaction is an re-

action. Therefore, both stereoisomers will be formed, regardless of the configuration of

the reactant.

Now continue on to Problem 25.

PROBLEM 25

Give the configuration(s) of the substitution product(s) that will be obtained from the reac-

tions of the following secondary alkyl halides with the indicated nucleophile:

a.

b.

c.

d.

e.

f.

PROBLEM 26 SOLVED

The rate law for the substitution reaction of 2-bromobutane and in 75% ethanol and

25% water at 30°C is

rate=3.20* 10 -^5 [2-bromobutane][HO-]+1.5* 10 -^6 [2-bromobutane]

HO-

H CH 3

C

CH 2 CH 3

+ CH 3 OH

Br

CH 3

Br

H C

CH 2 CH 3

high concentration

+ CH 3 O−

CH (^3) + CH 3 OH
Cl
H
H
high concentration
CH (^3) + CH 3 O−
Cl
H
H
C + NH 3
CH 2 CH 2 CH 3
CH 3 H
Cl
high concentration
C + CH 3 CH 2 CH 2 O−
CH 2 CH 3
CH (^3) H
Br
SN 1
CH 3 CH 2 CHCH 3 + H 2 O
I
CH 3
OH
C + H
CH 2 CH 3
CH 3 H
HO
C
CH 2 CH 3
SN 2
high concentration
CH 3 CH 2 CHCH 3 + HO−
Cl
CH 3 CH 2 CHCH 3
OH
SN 2
388 CHAPTER 10 Substitution Reactions of Alkyl Halides