JEE Main 2016 Chemistry question

ChemistryHaloalkanes and HaloarenesJEE Main 2016

2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields: (i) ; (ii) ; (iii)

Answer: (4)

Solution

2-Chloro-2-methylpentane is a **tertiary** halide, so it ionises readily to a stabilised tertiary carbocation, and both substitution and elimination pathways are open. The carbocation can be captured by the solvent or by methoxide to give the ether (i), 2-methoxy-2-methylpentane — the product. It

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Question ID VK-115459