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Intermediate involved in the following reaction is

Question and options

Intermediate involved in the following reaction is
Figure
  1. aryne
  2. aryl cation
  3. aryl anion
  4. aryl radical

Answer and explanation

Correct answer: A - aryne
Chlorotoluene with NaNH2\mathrm{NaNH_2} in liquid NH3\mathrm{NH_3} reacts by elimination-addition: loss of HCl gives a benzyne (aryne), and NH2−\mathrm{NH_2^-} adds to either end, giving a mixture of toluidines (cine substitution), as shown.

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