Question
Which of the following compounds undergo SN1/SN2 reaction? Explain.
(i) Benzyl chloride;
(ii) Chlorobenzene;
(iii) Chloroethene;
(iv) Chloroethyne
Answer :
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In nucleophilic substitution reactions, the feasibility of S_N1 or S_N2 mechanisms depends mainly on the nature of the carbon–halogen bond, the stability of the carbocation formed, and steric and electronic factors. (i) Benzyl chloride readily undergoes both S_N1 and S_N2 reactions. In the S_N1 mechanism, the C–Cl bond ionizes to form a benzyl carbocation, which is highly stabilized by resonance with the aromatic ring. This resonance stabilization lowers the energy barrier for carbocation formation, making the S_N1 reaction favorable. At the same time, the benzylic carbon is a primary carbon and is not sterically hindered, allowing a nucleophile to attack easily from the backside. Hence, benzyl chloride can also undergo S_N2 reactions, especially in the presence of strong nucleophiles. (ii) Chlorobenzene does not undergo either S_N1 or S_N2 reactions under normal conditions. In chlorobenzene, the lone pair of electrons on chlorine participates in resonance with
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Which of the following compounds undergo SN1/SN2 reaction? Explain.
(i) Benzyl chloride;
(ii) Chlorobenzene;
(iii) Chloroethene;
(iv) Chloroethyne
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