Q23 · CSIR-NET Chemistry, December 2014

Paper: CSIR-NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Easy

The products A and B in the following reaction sequence are Question structure 1 of 10, ABC26OR0253 Question structure 2 of 10, ABC26OR0253 Question structure 3 of 10, ABC26OR0253 Question structure 4 of 10, ABC26OR0253 Question structure 5 of 10, ABC26OR0253 Question structure 6 of 10, ABC26OR0253 Question structure 7 of 10, ABC26OR0253 Question structure 8 of 10, ABC26OR0253 Question structure 9 of 10, ABC26OR0253 Question structure 10 of 10, ABC26OR0253
(a)Option (a) structure 1 of 4, ABC26OR0253 Option (a) structure 2 of 4, ABC26OR0253 Option (a) structure 3 of 4, ABC26OR0253 Option (a) structure 4 of 4, ABC26OR0253
(b)Option (b) structure 1 of 3, ABC26OR0253 Option (b) structure 2 of 3, ABC26OR0253 B = Option (b) structure 3 of 3, ABC26OR0253
(c)Option (c) structure 1 of 3, ABC26OR0253 Option (c) structure 2 of 3, ABC26OR0253 B = Option (c) structure 3 of 3, ABC26OR0253
(d)Option (d) structure 1 of 3, ABC26OR0253 Option (d) structure 2 of 3, ABC26OR0253 B = Option (d) structure 3 of 3, ABC26OR0253
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
LDA deprotonates the α′ (C-6) position of the vinylogous ester and the iodide alkylates it (A, chloropropyl retained); MeMgBr adds 1,2 to the ketone and aqueous acid hydrolyses/eliminates the enol ether to the 3-methylcyclohexenone (c).

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