Q74 · CSIR-NET Chemistry, December 2012

Paper: CSIR-NET December 2012 · Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Sigmatropic Shifts · Marks: 2 · Difficulty: Medium

The following transformation involves Question structure 1 of 5, ABC26OR1023 Question structure 2 of 5, ABC26OR1023 Question structure 3 of 5, ABC26OR1023 Question structure 4 of 5, ABC26OR1023 Question structure 5 of 5, ABC26OR1023
(a)an iminium ion, [3, 3]-sigmatropic shift and Mannich reaction.
(b)a nitrenium ion, [3, 3]-sigmatropic shift and Michael reaction.
(c)an iminium ion, [1, 3]-sigmatropic shift and Mannich reaction.
(d)a nitrenium ion, [1,3]-sigmatropic shift and Michael reaction.
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
The aldehyde and methylamine form an iminium ion; a cationic 2-aza-Cope ([3,3]) rearrangement then places the enol and the new iminium for an intramolecular Mannich cyclisation (aza-Cope/Mannich).

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