The major product A and the byproducts B formed in the following reaction are

F1 Teaching Arbaz 29-05-2023 Ankit D10

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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Answer (Detailed Solution Below)

Option 1 : F1 Teaching Arbaz 29-05-2023 Ankit D11
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Detailed Solution

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Concept:

→ The Corey–Winter olefin synthesis (also known as Corey–Winter–Eastwood olefination) is a series of chemical reactions for converting 1,2-diols into olefins.

→ The reaction mechanism involves the formation of a cyclic thiocarbonate from the diol and thiophosgene.

→ The second step involves treatment with trimethyl phosphite, which attacks the sulfur atom, producing S=P(OMe)3 (driven by the formation of a strong P=S double bond) and leaving a carbene. This carbene collapses with loss of carbon dioxide to give the olefin.

F1 Teaching Arbaz 29-05-2023 Ankit D15

Mechanism:

F1 Teaching Arbaz 29-05-2023 Ankit D16
Conclusion:
The correct answer is option 1.

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