The major products A and B in the following reaction sequence are
F1 Savita Teaching 25-5-23 D42

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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  1. F1 Savita Teaching 25-5-23 D43
  2. F1 Savita Teaching 25-5-23 D44
  3. F1 Savita Teaching 25-5-23 D45
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Answer (Detailed Solution Below)

Option 2 : F1 Savita Teaching 25-5-23 D44
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Detailed Solution

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Concept:-

The reaction proceeds through nucleophilic addition followed by epoxide formation and finally goes via the Wharton reaction.

Wharton reaction: In this reaction reduction of \(\alpha ,\beta\) - epoxy ketones by hydrazine in the presence of AcOH occurs which gives an allylic alcohol.

 For example,
F1 Savita Teaching 25-5-23 D47
Explanation:-

     The mechanism of the reaction is as follows;
F1 Savita Teaching 25-5-23 D65

F2 Vinanti Teaching 04.12.23 D1

  • In the first step, the attack of hydroperoxyl nucleophile occurs followed by the epoxide formation and then the removal of the hydroxide ion to which compound A is formed.
  • Then hydrazine which is added to the ketone forms a hydrazone derivative. It facilitates the ring opening of epoxide followed by the removal of Nthe final product i.e. compound B we get is an allyl alcohol.

Conclusion:-

Hence, the major products A and B in the following reaction sequence are
F1 Savita Teaching 25-5-23 D44

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