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The product formed in the following reaction is
\(CH_{3} - CH_{2} - CH(CH_{3}) - CH(CH_{3}) - ONa + C_{2}H_{5}Br \to\)

  • A.2-Ethoxy-3-methylpentane
  • B.2-Ethoxy-4-methylpentane
  • C.1-Ethoxy-2-methylpentane
  • D.2-Ethoxy-2-methylpentane
  • E.5-Ethoxy-3-methylpentane

Answer: A

The product is 2-Ethoxy-3-methylpentane.

This is a Williamson ether synthesis: the alkoxide ion displaces bromide from bromoethane, attaching an ethyl group to the oxygen. The carbon skeleton of the alkoxide is unchanged: CH3CH2CH(CH3)CH(CH3)-O-C2H5.

The longest chain has five carbons; numbering from the end nearer the substituents puts the ethoxy group at C2 and the methyl at C3. '2-Ethoxy-4-methyl' numbers from the wrong end, and the other names describe different skeletons.

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