Which of the following reaction is NOT correctly represented?

- A
Methylbenzene + Benzyl bromide
- B
Benzene diazonium chloride + Bromobenzene
- C
Methylbenzene + (dark) Ortho- and para-bromotoluenes
- D
Methylbenzene + Benzyl bromide
Which of the following reaction is NOT correctly represented?

Methylbenzene + Benzyl bromide
Benzene diazonium chloride + Bromobenzene
Methylbenzene + (dark) Ortho- and para-bromotoluenes
Methylbenzene + Benzyl bromide
Correct answer:D
Standard Method
Given: Four represented reactions are shown for bromination and diazonium substitution.
Find: Which reaction is NOT correctly represented.
Step 1: Recall reaction types.
Step 2: Analyze each option.
Conclusion: Therefore, the correct option is D.
Reaction-Type Check
Given: The options test recognition of benzylic bromination, electrophilic aromatic substitution, and Sandmeyer reaction.
Find: The incorrectly represented reaction.
Use the reaction-condition check:
By this check, options A, B, and C match the expected chemistry. The solution states that D is the incorrectly represented entry because it is a duplicated representation of option A rather than a distinct correct reaction.
Therefore, the correct option is D.
Confusing benzylic radical substitution with electrophilic aromatic substitution. Under , bromination occurs at the benzylic position, not on the ring. Use reaction conditions to decide the reaction type first.
Ignoring the role of Lewis acid such as or . These conditions promote bromination on the aromatic ring, so option C should not be treated as benzylic bromination.
Missing the Sandmeyer reaction pattern. Diazonium salts with copper halide reagents form aryl halides, so option B is a standard conversion and should not be marked incorrect.
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