Carboxylic acids and derivatives (A-level only)

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Question 5
Medium

An acyl chloride, (CH3)2CHCOCl\text{(CH}_3)_2\text{CHCOCl}(CH3​)2​CHCOCl (2-methylpropanoyl chloride), is a valuable reagent in organic synthesis. It reacts with benzene in the presence of anhydrous AlCl3\text{AlCl}_3AlCl3​ catalyst via an electrophilic substitution reaction.

a.

Give an equation for the reaction of (CH3)2CHCOCl\text{(CH}_3)_2\text{CHCOCl}(CH3​)2​CHCOCl with AlCl3\text{AlCl}_3AlCl3​ to form the active electrophile. Outline a mechanism for the reaction of this electrophile with benzene to form the phenyl ketone product.

[4]
b.

The ketone product from part 1 can be converted into the alcohol shown in the figure below:

Chemical structure of 2-methyl-1-phenylpropan-1-ol

Give the IUPAC name of this alcohol. Give a suitable reagent needed for this conversion and name the mechanism of the reaction.

[3]
c.

This alcohol reacts with ethanoyl chloride (CH3COCl\text{CH}_3\text{COCl}CH3​COCl) to form an ester.

Describe what would be observed during this reaction. Name the mechanism for the formation of the ester, and draw its structural formula.

[3]

Carboxylic acids and derivatives (A-level only) Questions

  1. A Level
  2. /Chemistry
  3. /Carboxylic acids and derivatives (A-level only)