JEE Main Chemistry question

Which one of the following will most readily be dehydrated in acidic conditions? (Four isomeric hydroxy-ketone structures are given, differing in the relative position of and .) **[BCECE 2008]**

(A)1-hydroxy-pentan-3-one type (OH and C=O separated by one CH2)
(B)4-hydroxy-pentan-2-one type
(C)Compound whose dehydration gives a conjugated enone (OH beta to C=O)Correct
(D)Compound whose dehydration product is not conjugated

Answer: (C)

Solution

Among isomeric hydroxy-ketones, the one in which the is positioned so that its dehydration directly produces a conjugated -unsaturated ketone (an enone) is dehydrated most readily, because the product is stabilised

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Question ID VK-148454