The major product formed in the following reaction is · ABC26OR0653

Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Easy

The major product formed in the following reaction is Question structure 1 of 2, ABC26OR0653 Question structure 2 of 2, ABC26OR0653
(a)Option (a) structure, ABC26OR0653
(b)Option (b) structure, ABC26OR0653
(c)Option (c) structure, ABC26OR0653
(d)Option (d) structure, ABC26OR0653
Answer
Answer: D ✓ checked by 4AB · confidence low
Explanation
The t-butyl group locks the ring with t-Bu equatorial; the epoxide O is cis to t-Bu. Azide opens the epoxide by anti (SN2) attack through the chair-like transition state (Fürst–Plattner rule), so the product is formed trans-diaxial. In that chair, an axial group on C-1 (the epoxide carbon 1,4 to t-Bu) is cis to t-Bu, and an axial group on C-2 (1,3 to t-Bu) is trans to it. The oxygen keeps its face (cis to t-Bu), so OH is on C-1 and N₃ enters C-2, trans to t-Bu: OH wedged on the remote carbon, N₃ hashed on the carbon nearer t-Bu. Answer (d).

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