33.2 A2 Level

Esters

7 flashcards to master this topic

Definition Flip

What type of reaction is used to produce esters from alcohols and acyl chlorides?

Answer Flip

Esters are produced via a nucleophilic acyl substitution reaction. The alcohol acts as a nucleophile, attacking the carbonyl carbon of the acyl chloride, resulting in the displacement of chloride ion and formation of the ester.

Calculation Flip

Write the general equation for the formation of an ester from an alcohol and an acyl chloride.

Answer Flip

R'OH + RCOCl → RCOOR' + HCl, where R'OH is the alcohol, RCOCl is the acyl chloride, and RCOOR' is the ester.

Key Concept Flip

Give the reagents required for the synthesis of ethyl ethanoate.

Answer Flip

To synthesize ethyl ethanoate, you would need ethanol (CH₃CH₂OH) and ethanoyl chloride (CH₃COCl).

Key Concept Flip

Draw the mechanism for the reaction of ethanol with ethanoyl chloride to produce ethyl ethanoate.

Answer Flip

Ethanol attacks the carbonyl carbon of ethanoyl chloride. The C=O bond breaks, forming a tetrahedral intermediate. Chloride ion leaves, the C=O reforms, and a proton is lost, yielding ethyl ethanoate and HCl.

Key Concept Flip

What are the products formed in the reaction between phenol and benzoyl chloride?

Answer Flip

The reaction between phenol (C₆H₅OH) and benzoyl chloride (C₆H₅COCl) yields phenyl benzoate (C₆H₅COOC₆H₅) and hydrochloric acid (HCl).

Key Concept Flip

Outline the steps in the mechanism for the formation of phenyl benzoate from phenol and benzoyl chloride.

Answer Flip

Phenol attacks the carbonyl carbon of benzoyl chloride. Chloride ion is eliminated, and a proton is removed from the intermediate, resulting in the formation of phenyl benzoate and HCl.

Key Concept Flip

Why is the reaction between an alcohol and an acyl chloride a more effective method for ester formation compared to reacting the alcohol with a carboxylic acid directly?

Answer Flip

Acyl chlorides are more reactive than carboxylic acids due to the electron-withdrawing chlorine atom making the carbonyl carbon more electrophilic. This leads to a faster and higher-yielding reaction at lower temperatures.

Ready to test yourself?

Practice with MCQ questions to check your understanding of Esters.

Take Quiz
33.1 Carboxylic acids 33.3 Acyl chlorides