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Organic Chemistry and Analysis

Acyl chlorides and their reactions with alcohols, amines and ammonia

  • 3 things to know
  • Components 02 and 03

Overview

Recall questions on making an acyl chloride with thionyl chloride, and on the products with water, alcohols, primary and secondary amines and ammonia.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Numbers

Why does base hydrolysis of an ester go to completion, what is the equation for a carboxylic acid with thionyl chloride, and what forms when an acyl chloride reacts with an alcohol?

Numbers

Write the general equation for the hydrolysis of an acyl chloride.

Key term

What type of ester is formed when phenol reacts with an acyl chloride?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Name the reagent used to convert a carboxylic acid into an acyl chloride.

    Model answer

    Thionyl chloride (SOCl₂).

  2. 2

    Write the general equation for the reaction of a carboxylic acid with thionyl chloride.

    Model answer

    RCOOH + SOCl₂ → RCOCl + SO₂ + HCl

  3. 3

    What are the products when an acyl chloride reacts with an alcohol?

    Model answer

    An ester and hydrogen chloride.

  4. 4

    Write the general equation for the reaction of an acyl chloride with an alcohol.

    Model answer

    RCOCl + R′OH → RCOOR′ + HCl

  5. 5

    Write the general equation for the hydrolysis of an acyl chloride.

    Model answer

    RCOCl + H₂O → RCOOH + HCl

  6. 6

    What are the products when an acyl chloride reacts with a primary amine?

    Model answer

    A secondary amide and hydrogen chloride.

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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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