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COMEDK2024ChemistryHaloalkanes and HaloarenesActual

In a set of reactions, bromoethane yielded a final product 'S'. The compound 'S' should be

Options

  1. APropane-1, 3-dioic acid
  2. BPentane-1, 5-dioic acid
  3. CProp-2-enoicacid
  4. DButane-1, 4-dioic acid

Correct answer

D. Butane-1, 4-dioic acid

Step-by-step solution

Bromoethane ( CH₃CH₂Br ) reacts with alcoholic KOH to undergo dehydrohalogenation, forming ethene ( P = CH₂=CH₂ ). Ethene reacts with Br₂/CCl₄ to undergo electrophilic addition, forming 1,2-dibromoethane ( Q = BrCH₂CH₂Br ). 1,2-dibromoethane reacts with excess KCN to undergo nucleophilic substitution, replacing both bromine atoms with cyano groups to form succinonitrile ( R = NC-CH₂CH₂-CN ). Succinonitrile undergoes acid-catalyzed hydrolysis ( H₃O⁺ ) to convert the cyano groups into carboxylic acid groups, yielding

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