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Question

Which of the following, upon treatment with tert-BuONa followed by the addition of bromine water, fails to decolorize the color of bromine?


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Solution

The correct option is C

Potassium tert-butoxide is a non-nucleophilic basic, as we know. It's really quite huge in size. As a result, it facilitates the elimination process. The E-2 mechanism is engaged in the process.

The correct answer is option C

Explanation

The nucleophile can operate as a base, permitting acidic catalyzing of the hydrolysis and nucleophilic substitution transformations. The strength of the nucleophile will decide this. If the nucleophile's nucleophilic strength is weak, it will be eliminated; if it is high, it will be exchanged.
Except for option C, it has a leaving group at the alpha position, all other molecules have double bonds. As a result, there will be elimination processes. Option C is the only one that will not have an elimination reaction.
Option C includes the following reaction:

Option A is incorrect because

Option B is incorrect because

Option D is incorrect because

Therefore, option C is the correct answer.


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