Q17 · CSIR NET Chemistry, December 2014
Paper: CSIR NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The major product of the following reaction is: 
[ egin{array}{l} 3. mathrm{H_2O, OH^{-}} \ 4. mathrm{H^{+}} end{array} ]
(a)
(b)
(c)
(d)
Answer
Answer: A ✓ checked by 4AB · confidence low
Skeleton certain; the relative stereochemistry of CN/COOEt between (a) and (b) is not decidable from the crop.
Explanation
The pyrrolidine enamine forms toward the less hindered CH₂ and is alkylated by the allylic bromide; after hydrolysis, base generates the other enolate (at the methyl-bearing carbon), which adds intramolecularly (Michael) to the cyanoacrylate, giving the azabicyclo[3.3.1]nonanone with the methyl at the bridgehead (a).
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