Year 2 Organic Extra Stuff

Question 1

How do you produce an Acyl Chloride?

Answer 1

Carboxylic Acid+ Thionyl Chloride (SOCl2)

Question 2

Example Equation for preparation of acyl chlorides

Answer 2

CH3COOH + SOCl2 –> CH3COCl + SO2 +HCl

Question 3

What do acyl chlorides react with?

Answer 3

1. Water
2. Ammonia
3. Alcohols
4. Primary Amines

Question 4

Acyl Chloride Reaction with water

Answer 4

Violent reaction takes place, forming Carboxylic Acid & HCl fumes
CH3COCl + H2O –> CH3COOH + HCl

Question 5

Acyl Chloride Reaction with ammonia

Answer 5

CH3COCl + 2NH3 –> CH3CONH2 + NH4Cl

Question 6

Acyl Chloride reaction with Alcohols

Answer 6

Forms Ester
CH3COCl + CH3OH –> CH3COOCH3 + HCl

Question 7

Acyl chloride reaction with primary amine

Answer 7

Forms Secondary Amide
CH3COCl + 2CH3NH2 –> CH3CONHCH3 + CH3NH3Cl

Question 8

How are acid anhydrides formed?

Answer 8

They are formed by the removal of water from two carboxylic acid molecules which are the same.

Question 9

How do acid anhydrides react?

Answer 9

Similarly to acyl chlorides but much less vigorously

Question 10

Acid anhydride reaction with alcohol

Answer 10

Produces an ester and a carboxylic acid. Less vigorous than acyl chloride and doesn’t produce HCl.

Question 11

Reaction of Acyl Chloride with phenol

Answer 11

Forms ESTER +HCl

Question 12

Formation of ester from alcohol + carboxylic acid

Answer 12

alcohol + carboxylic acid –> ester + water
e.g. propanoic acid + methanol –> methyl propanoate + water

Question 13

Downside of producing an ester from alcohol + carboxylic acid

Answer 13

1. Reversible reaction
2. Must be heated under reflux
3. requires conc H2SO4 catalyst.