Q10 · CSIR-NET Chemistry, June 2017
Paper: CSIR-NET June 2017 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The correct combination of reagents to effect the following reaction is: 
(a)i) $\mathrm{POCl}_{3}$, pyridine; ii) AgoAc ; iii) $\mathrm{LiAlH}_{4}$
(b)i) $\mathrm{NaBH}_{4}$; ii) $\mathrm{Ph}_{3} \mathrm{P}$, DEAD, $\mathrm{PhCO}_{2} \mathrm{H}$
(c)i) $\mathrm{Ph}_{3} \mathrm{P}, \mathrm{DEAD}, \mathrm{PhCO}_{2} \mathrm{H}$; ii) $\mathrm{LiAlH}_{4}$
(d)i) PCC; ii) L-selectride
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
Mitsunobu (Ph₃P/DEAD/PhCO₂H) inverts the secondary carbinol as its benzoate while the aldehyde is untouched; LiAlH₄ then reduces the aldehyde to CH₂OH and cleaves the benzoate, giving the inverted diol (c).
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