Q26 · CSIR NET Chemistry, December 2013
Paper: CSIR NET December 2013 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
In the following transformation, the reagent A and the major product B, respectively, are 
$\xrightarrow{\mathrm{A}}$ 
$\xrightarrow{\mathrm{Ac_2O}/\Delta}\ \mathrm{B}$
$\xrightarrow{\mathrm{A}}$ $\xrightarrow{\mathrm{Ac_2O}/\Delta}\ \mathrm{B}$(a)
and 
and (b)
and 
and (c)
and 
and (d)
and 
and Answer
Answer: D ✓ checked by 4AB · confidence high
Explanation
m-CPBA (A) gives the pyridine N-oxide. In the Boekelheide rearrangement with Ac₂O the 2-methyl group, which is α to the N-oxide, becomes CH₂OAc, giving 3-methyl-2-(acetoxymethyl)pyridine (d).
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