Reactions of Carboxylic Acids
In this problem we shall consider four carboxylic acid
reactants:
butanoic acid
benzoic acid
cyclopentanecarboxylic acid
2,2-dimethyl propanoic acid
These compounds may be reacted with nine different
reagents:
LiAlH
4
in ether
(aqueous acid workup)
SOCl
2
& heat
(or PCl
3
& heat)
CH
3
CH
2
OH
acid catalyst , heat (–H
2
O)
CH
2
N
2
in ether
(i) NaOH
(1 equiv.)
(ii) C
6
H
5
CH
2
Br
Br
2
& heat
PBr
3
catalyst
(i) CH
2
N
2
in ether
(ii) 2 CH
3
MgBr
in ether
(i) SOCl
2
& heat
(ii) 2 C
6
H
5
NH
2
(aniline)
(i) SOCl
2
& heat
(ii) p-xylene
& AlCl
3
+ heat
Select one carboxylic acid from the first group,
and one reagent from the second group.
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