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Chapter 17: Q17-60E (page 567)

Benzyl chloride can be converted intobenzaldehyde by treatment with nitromethane and base. The reactioninvolves the initial conversion of nitromethane in to its anion, followed by SN2 reaction of the anion with benzyl chloride and subsequent E2 reaction. Write the mechanism in detail, using curved arrows to indicate the electron flow in each step.

Benzyl chloride Nitromethane anion Benzaldehyde

Short Answer

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Step by step solution

01

Types of organic reactions

In a nucleophilic substitution reaction, the reactant molecules are attacked by nucleophiles like anions or electron-rich groups. But in elimination reactions, the groups undergo elimination due to the electron rearrangement from the molecule.

02

Explanation

The mechanism for converting Benzyl chloride into benzaldehyde on treatment with nitromethane and base is shown below.

Mechanism

Step 1 is the nucleophilic substitution reaction, and step 2 is the elimination reaction. In the first step, the base attacks the nitromethane anion, substituting the anion with the compound. In the second step, the elimination of the nitromethyl anion occurs as a result of the base's attack

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