Chem 212

Carboxylic Acid Derivatives Problems Provide the products for the following reactions. Show a complete mechanism for each reaction

O
O SOCl2 O
O O
OH O
OH Cl O
O
+
OH

O O
MeOH
Ph O
Ph OMe
Cl pyridine
OMe 1. LiAlH4 OH
+
2. H3O

O
O O O
OH
Ph Ph
Cl pyridine O O O
HNMe2 + MeOH
Ph Ph
OMe NMe2

O O
HNMe2
Cl NMe2 NH2
1. LiAlH4 NH2
pyridine
O 2. H3O+

O O
HNMe2 O
OH H2NMe2 O
O 1. NaH
Ph Ph
OH O
2.
Br

O EtOH O

OH H+ catalyst OEt NH2

1. NaOH, heat OH
O 2. H3O+
O

O O
1. NaOH, ∆
O OH
2. H3O+ Ph O MeOH Ph OMe HO

O O O O
Ph OH MeO

O O
MeO HO
O
1. LiAlH4 1. LiAlH4
Et2N Et2N
2. H3O+ 2. H3O+
O

O
+
O O OMe O
MeOH H2O OH
O OH
N H3 O+, ∆ O

O
O O H2NMe
NHMe 1. LiAlH4
O NH2
O N 2. H3O+
+ H3NMe
O