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Question

An alcohol (A) on dehydration gives (B) which adds bromine molecule to give (C). (C) on heating with sodamide gives (D) which on hydration in the presence of Hg++/H2SO4 gives (E). E on reduction by lithium aluminium hydride gives (A). (E) is also obtained on dry distillation of calcium salt of acetic acid. How many enolisable proton present in the product (E)?

A
2
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B
6
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C
3
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D
0
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Solution

The correct option is B 6
By given hint, it is clear that E is acetone hence overall sequences of reactions will be

929971_938795_ans_4ebf91ba577d452ea6a0653254946604.png

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