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The Reaction of Butanols with HBr

Reaction Stoichiometry for 1-butanol:

OH + HBr + H 2O
Br

Mechanism for 1-butanol (an SN2 reaction)

Step 1: Protonation of alcohol (fast)


O O
OH
OH + H O S OH
H
O S OH

O O
Step 2: Nucleophillic attack of bromide ion (slow-RDS)

Br -
OH Br + H 2O
H

Possible competing side reactions:

1. E2 elimination

OH + H 2O + H 3O +
H H

O
H H
Increasing sulfuric acid concentration will decrease HOH concentration
(why?), therefore this side reaction should occur less often.

2. Competing SN2 reaction (formation of ether)


OH
+ H 2O
O

OH
H
Increasing sulfuric acid concentration will also decrease unprotonated
alcohol concentration (why?), therefore this side reaction should also occur less often.
Mechanism for 2-butanol (an SN1 reaction)
Step 1: Protonation of alcohol (fast)
O
O
OH
H O S OH
OH 2 O S OH
O
O

Step 2: Loss of water leaving group (slow-RDS)

OH 2
+ H 2O

Step 3: Nucleophillic attack of bromide ion onto carbocation (fast)


Br-

Br
Possible competing side reactions:

1. Competing SN1 reaction (formation of ether)


OH 2

fast
fast
O O + H3O +
H2O
HO H

Increasing sulfuric acid concentration will decrease unprotonated alcohol


concentration (why?), therefore this side reaction should occur less often.

2. E1 elimination followed by polymerization


H2O

H
+ H3O+

growing
polymer

Increasing sulfuric acid will slightly decrease water concentration but will
greatly increase carbocation concentration, so this side reaction should happen more often
with increasing sulfuric acid concentration.