How would you synthesize the following compounds from butanenitrile using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Example: ab Reagents 1. NaOH / H2O 2. H3O* SOCI2 1. NABH4 2. H3O* a e i 1. ВНз / THF 2. H2O2 / NaOH b f 1. LIAIH4 2. H30* 1. CH3CH2MgBr / dry ether 2. Hзо j 1. (CH3)2CHMgBr / dry ether 2. Hзо PBR3 g NaCN k d Dess-Martin Cro3 / H3O* conc. HCI periodinane in CH2CI2 a) 1-Butanol b) 2-Methyl-3-hexanone

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter16: Synthesis Workshop 1
Section: Chapter Questions
Problem 28E
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How would you synthesize the following compounds from butanenitrile using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Example: ab
Reagents
1. NaOH / H2O
2. H3O*
SOCI2
1. NaBH4
a
e
i
2. H3O*
1. ВНз / THF
2. H202 / NaOH
b
f
1. LIAIH4
1. CH3CH2MGB I dry ether
2. H3O*
2. H3O*
1. (CH3)2CHMgBr / dry ether
2. H30*
PBr3
NaCN
k
d
Dess-Martin
h
Cro3 / H3O*
conc. HCI
periodinane in CH2CI2
a) 1-Butanol
b) 2-Methyl-3-hexanone
Transcribed Image Text:How would you synthesize the following compounds from butanenitrile using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Example: ab Reagents 1. NaOH / H2O 2. H3O* SOCI2 1. NaBH4 a e i 2. H3O* 1. ВНз / THF 2. H202 / NaOH b f 1. LIAIH4 1. CH3CH2MGB I dry ether 2. H3O* 2. H3O* 1. (CH3)2CHMgBr / dry ether 2. H30* PBr3 NaCN k d Dess-Martin h Cro3 / H3O* conc. HCI periodinane in CH2CI2 a) 1-Butanol b) 2-Methyl-3-hexanone
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