Q9 · CSIR-NET Chemistry, December 2018
Paper: CSIR-NET December 2018 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reduction Reagents · Marks: 2 · Difficulty: Medium
Correct sequence of reagents to be used for the following conversion is- 
(a)I) NaH, 1-fluoronaphthalene; II) $\mathrm{NaBH_{4}}$; III) i. ($\mathrm{CH_{2}O}$)n, Me2NH.HCl; ii. 5N NaOH
(b)I) $\mathrm{NaBH_{4}}$; II) NaH, 1-fluoronaphthalene; III) i. ($\mathrm{CH_{2}O}$)n, Me2NH.HCl; ii. 5N NaOH
(c)I) ($\mathrm{CH_{2}O}$)n, Me2NH.HCl; ii. 5N NaOH; II) $\mathrm{NaBH_{4}}$; III) NaH, 1-fluoronaphthalene
(d)I) i. ($\mathrm{CH_{2}O}$)n, Me2NH.HCl; ii. 5N NaOH; II) NaH, 1-fluoronaphthalene
Answer
Answer: C ✓ checked by 4AB · confidence high
Explanation
The duloxetine route: a Mannich reaction ((CH₂O)n, Me₂NH·HCl) gives the β-amino ketone, NaBH₄ reduces it to the alcohol, and NaH/1-fluoronaphthalene forms the aryl ether by SNAr (c).
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