Alcohols (Cambridge (CIE) A Level Chemistry): Flashcards

An acyl chloride is an organic compound containing a -COCl functional group, where the carbonyl carbon is electron-deficient and susceptible to nucleophilic attack.

Acyl chlorides are more reactive so the ester forms faster, and the reaction goes to completion so the maximum yield of ester is produced.

True.

The C-Cl bond breaks during nucleophilic attack by the alcohol's -OH group, releasing HCl as white fumes.

When an acyl chloride reacts with an alcohol, the -OH group acts as a nucleophile and attacks the carbonyl carbon to substitute the chlorine atom, forming an ester.

A base (e.g. NaOH) is required. The base deprotonates phenol to form the phenoxide ion, which is a better nucleophile and can attack the carbonyl carbon. The reaction proceeds at room temperature.

False.

Aliphatic alcohols react vigorously with acyl chlorides at room temperature without a base. Phenol also reacts at room temperature but requires a base (e.g. NaOH) to form the phenoxide ion before nucleophilic attack can occur.

A phenoxide ion is the conjugate base of phenol, formed when phenol is deprotonated by a base. It is a better nucleophile than phenol because the negative charge makes the oxygen more electron-rich.

Addition-elimination: the nucleophile (alcohol or phenoxide) adds across the C=O bond, then HCl is eliminated to form the ester.

In the reaction of an acyl chloride with phenol, a base must first form the phenoxide ion, which then attacks the carbonyl carbon.