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Q.

The major product in the reaction of ethyl chloride with ethanolic AgCN

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a

Nitroethane

b

Ethyl nitrate

c

Ethyl isocyanide

d

Ethyl cyanide

answer is B.

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Detailed Solution

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Ethyl Chloride and Silver Cyanide Reaction

Major Product of Ethyl Chloride with Ethanolic Silver Cyanide

The major product formed when ethyl chloride (C2H5Cl) reacts with alcoholic silver cyanide (AgCN) is ethyl isocyanide (C2H5NC), not ethyl cyanide (C2H5CN).

Explanation:

  • When ethyl chloride undergoes nucleophilic substitution with AgCN in an alcoholic medium, the cyanide ion (CN-) from AgCN attacks the ethyl carbocation intermediate. However, due to the nature of AgCN, the nitrogen atom of the cyanide group links to the ethyl group instead of the carbon atom, resulting in the formation of an isocyanide (also called isonitrile).
  • The reaction proceeds as follows: 
    C2H5Cl → C2H5NC + AgCl
  • Ethyl isocyanide is a functional isomer of ethyl cyanide but differs in the connectivity of the cyanide functional group.
  • Silver chloride (AgCl) precipitates out of the solution as a byproduct.

Key Points:

  • With AgCN, the reaction favors formation of isocyanides.
  • With potassium cyanide (KCN) or sodium cyanide (NaCN), the product would predominantly be alkyl cyanides (like ethyl cyanide).
  • This difference arises because AgCN is covalent and attacks via nitrogen, whereas ionic cyanides attack via carbon.

Thus, the major product of the reaction of ethyl chloride with ethanolic silver cyanide is ethyl isocyanide (C2H5NC).

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