Carboxylic acids and derivatives (A-level only)

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Question 2
Medium

An acyl chloride, CH3CH2CH2COCl\text{CH}_3\text{CH}_2\text{CH}_2\text{COCl}CH3​CH2​CH2​COCl (butanoyl chloride), is a useful reagent in organic synthesis. It reacts with benzene in the presence of anhydrous AlCl3\text{AlCl}_3AlCl3​ catalyst via an electrophilic substitution reaction.

1.

Give an equation for the reaction of CH3CH2CH2COCl\text{CH}_3\text{CH}_2\text{CH}_2\text{COCl}CH3​CH2​CH2​COCl 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]
2.

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

Chemical structure of 1-phenylbutan-1-ol. It consists of a central CH group attached to a phenyl ring on the left, a hydroxyl (OH) group pointing downwards to the right, and a propyl (CH2CH2CH3) group pointing upwards to the right.

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

[3]
3.

This alcohol reacts with propanoyl chloride (CH3CH2COCl\text{CH}_3\text{CH}_2\text{COCl}CH3​CH2​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 structure.

[3]

Carboxylic acids and derivatives (A-level only) Questions

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