13- Acyl chloride reactions

covers: water, alcohol, ammonia, primary amines

What is the functional group change when an acyl chloride reacts with water?

Acyl chloride → carboxylic acid.

What reagent is used when an acyl chloride reacts with water?

Water.

What are the conditions when an acyl chloride reacts with water?

Room temperature.

What are the products of acyl chloride + water?

Carboxylic acid + HCl.

Write the general equation for acyl chloride + water.

RCOCl + H₂O → RCO₂H + HCl.

What observation occurs during acyl chloride + water?

Steamy white fumes of HCl are given off.

What mechanism occurs during acyl chloride + water?

Nucleophilic addition–elimination.

What is the functional group change when an acyl chloride reacts with an alcohol?

Acyl chloride → ester.

What reagent is used in acyl choride + alcohol?

An alcohol.

What are the conditions for a/c + alcohol?

Room temperature.

What are the products in a/c + alcohol?

Ester + HCl.

Write the general equation for a/c + alcohol.

RCOCl + R′OH → RCOOR′ + HCl.

What observation occurs during a/c + alcohol?

Steamy white fumes of HCl are given off.

What mechanism occurs during a/c + alcohol?

Nucleophilic addition–elimination.

Why is using an acyl chloride a better method of making an ester than reacting a carboxylic acid with an alcohol?

The reaction is much quicker and is not reversible.

What is the functional group change when an acyl chloride reacts with ammonia?

Acyl chloride → primary amide.

What reagent is used for acyl chloride + ammonia?

Ammonia.

What are the conditions for a/c + ammonia?

Room temperature.

What are the products for a/c + ammonia?

Primary amide + ammonium chloride.

Write the general equation for a/c + ammonia.

RCOCl + 2NH₃ → RCONH₂ + NH₄Cl.

Why are two moles of ammonia required?

One mole reacts with the acyl chloride and the other neutralises the HCl produced to form NH₄Cl.

What observation may occur during a/c + ammonia?

White smoke of ammonium chloride can be produced.

What mechanism occurs during a/c + ammonia?

Nucleophilic addition–elimination.

What is the functional group change when an acyl chloride reacts with a primary amine?

Acyl chloride → secondary amide.

What reagent is used for acid chloride + primary amine?

A primary amine.

What are the conditions for a/c + primary amine?

Room temperature.

What are the products for a/c + primary amine?

Secondary amide + alkylammonium chloride salt.

Write the general equation for a/c + primary amine.

RCOCl + 2R′NH₂ → RCONHR′ + R′NH₃⁺Cl⁻.

Why are two moles of primary amine required?

One mole reacts with the acyl chloride and the other reacts with the HCl produced to form an alkylammonium chloride salt.

What mechanism occurs during a/c + primary amine?

Nucleophilic addition–elimination.