Acyl chlorides

Question 1

How can an acyl chloride be formed?

Answer 1

The reaction of carboxylic acid with (liquid) sulfur dichloride oxide (SOCl2)

Question 2

What is an addition-elimination reaction? Provide 3 examples.

Answer 2

In this reaction the addition of a small molecule across the C=O bond occurs, followed by removal of a small molecule.
E.g
Hydrolisis
Alcohols and Phenols to form esters
Ammonia and amines to form amides.

Question 3

What occurs when a acyl chloride is hydrolised?

Answer 3

A carboxylic acid and HCl molecule will be formed, an example of an addition-elimination reaction.

Question 4

What can acyl chloride react with to from an ester? (reagants) By products?

Answer 4

Either alcohols or phenols, requires heat and a base. HCl formed as by-product.

Question 5

Carboxylic acids require concentrated H2SO4 to be esterified, why does this differ from acyl chlorides?

Answer 5

Acyl chlorides are more reactive and can go to completion. Thus, only require heat and a base.

Question 6

What can acyl chloride react with to form amides? What type of reaction? What is the difference in products?

Answer 6

Either ammonia or an amine. Condensation. Ammonia will form a primary amide, and amines will form a secondary amide.