Q10 · CSIR NET Chemistry, June 2016
Paper: CSIR NET June 2016 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The correct reagent combination to effect the following reaction is: 
$\rightarrow$ 
$\rightarrow$ (a)(i) $\mathrm{NaBH_4,\ CeCl_3,\ MeOH,\ 0^{\circ}C}$ (ii) $\mathrm{H_2,\ [Ir(COD)(py)P(Cy)_3][PF_6]}$ (iii) $\mathrm{Ph_3P,\ PhCO_2H,\ DEAD}$ (iv) $\mathrm{LiAlH_4}$
(b)i) Li, liquid $\mathrm{NH}_{3}$ ii) $\mathrm{H}_{2},\left[\operatorname{Ir}[\mathrm{COD})(\mathrm{py}) \mathrm{P}(\mathrm{Cy})_{3}\right] \mathrm{PF}_{6}$ iii) $\mathrm{Ph}_{3} \mathrm{P}, \mathrm{PhCO}_{2} \mathrm{H}, \mathrm{DEAD}$ iv) $\mathrm{NaBH}_{4}, \mathrm{CeCl}_{3}, \mathrm{MeOH}, 0^{\circ} \mathrm{C}$
(c)i) $\mathrm{H}_{2}, \mathrm{Pd} / \mathrm{C}$ ii) $\mathrm{LiAlH}_{4},-78^{\circ} \mathrm{C}$
(d)i) $\mathrm{H}_{2}$, Pd/C ii) Li , liquid $\mathrm{NH}_{3}$
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
Luche reduction (NaBH₄/CeCl₃) gives the allylic alcohol from the convex face; Crabtree's catalyst hydrogenates the alkene directed by that OH; Mitsunobu with benzoic acid inverts the carbinol and LiAlH₄ removes the benzoate — (a).
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