Which of the following compounds is least reactive in nucleophilic substitution

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Question: Which of the following compounds is least reactive in nucleophilic substitution reactions? (2023)

Options:

Correct Answer: Benzyl bromide

Exam Year: 2023

Solution:

Benzyl bromide is less reactive in nucleophilic substitution due to the resonance stabilization of the benzyl cation formed during the reaction.

Which of the following compounds is least reactive in nucleophilic substitution reactions? (2023)

Which of the following compounds is least reactive in nucleophilic substitution reactions? (2023)

Step 1: Understand what nucleophilic substitution reactions are. These are reactions where a nucleophile (a species that donates an electron pair) replaces a leaving group (like bromine) in a compound.
Step 2: Identify the compounds being compared. In this case, we are looking at benzyl bromide and other compounds.
Step 3: Recognize that the reactivity in these reactions can depend on the stability of the intermediate formed during the reaction.
Step 4: Learn about resonance stabilization. This means that the positive charge in the intermediate (the benzyl cation) can be spread out over multiple atoms, making it more stable.
Step 5: Conclude that since benzyl bromide forms a stable benzyl cation due to resonance, it is less reactive in nucleophilic substitution compared to other compounds that do not have this stabilization.

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