Acyl chlorides

Question 1

Preparation of Acyl chlorides

Answer 1

1. Carboxylic acid with PCl5
2. Carboxylic acid with SOCl2
3. Carboxylic acid with PCl3

Question 2

Carboxylic acid with PCl5

Answer 2

Condition: anhydrous
RCOOH + PCl5 –> RCOCl + POCl3 + HCl

Question 3

Carboxylic acid with SOCl2

Answer 3

Condition: anhydrous
RCOOH + SOCl2 –> RCOCl + SO2 + HCl

Question 4

Carboxylic acid with PCl3

Answer 4

Condition: anhydrous
RCOOH + PCl3 –> RCOCl + H3PO3

Question 5

With water

Answer 5

Type of reaction: addition-elimination
Condition: dry reagents and glassware
Change in functional group: acyl chloride –> carboxylic acid

Question 6

With alcohols

Answer 6

Type of reaction: addition-elimination, esterification
Condition: mix at room temperature

alcohol + acyl chloride –> ester + HCl

Question 7

With concentrated ammonia

Answer 7

Type of reaction: addition-elimination
Condition: mix at room temperature
Change in functional group: acyl chloride –> amide

Question 8

With amines

Answer 8

Type of reaction: addition-elimination
Condition: mix at room temperature
Change in functional group: acyl chloride –> substituted amide

Question 9

With LiAlH4

Answer 9

Type of reaction: reduction
Condition: in dry ether then acid workup
Change in functional group: acyl chloride –> primary alcohol