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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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
Transcribed Image Text: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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