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EBK A SMALL SCALE APPROACH TO ORGANIC L

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter41: 1,4-diphenyl-1,3-butadiene

Section: Chapter Questions

Problem 1Q

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8. How would you synthesize the following compounds from butanenitrile using reagents from the table? Answers
range from 1 to 5 steps.
Reagents
SOCI₂
a
1. NaOH / H₂O
e
i
1. NaBH4
2. H3O+
2. H₂O*
b
1. BH3/THF
f
1. LiAlH4
j
2. H₂O₂ / NaOH
2. H₂O*
1. CH3CH2MgBr / dry ether
2. H₂O*
C
PBr3
g
NaCN
k
1. (CH3)2CHMgBr / dry ether
2. H3O+
d
Dess-Martin
h
KMnO4 / H3O+
I
conc. HCI
periodinane in CH2Cl2
a.
CH3CH2CH2CH2NH2
b. 3-hexanol
C.
Butanal
d. Pentanoic acid

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