How would you synthesize the following compounds from cyclohexanone using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Reagents a 1. CH3MgBr / dry ether 2 H3O+ e 1. OsO4 i 1. BH3/THF 2. NaHSO3/H₂O 2. H₂O₂ / NaOH b 1. C6H5 MgBr / dry ether f 1. NaBH4 j Mg / dry ether 2 H3O+ 2. H3O+ C PBг3 g HOCH2CH2OH/HCI k H2/Pd d m-chloroperbenzoic h H3O+ / heat 1 CrO3 / H3O+ acid a) 2-phenylcyclohexanone b) cyclohexylbenzene m cyclohexanone

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 29VC
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How would you synthesize the following compounds from cyclohexanone using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Reagents
a
1. CH3MgBr / dry ether
2 H3O+
e
1. OsO4
i
1. BH3/THF
2. NaHSO3/H₂O
2. H₂O₂ / NaOH
b
1. C6H5 MgBr / dry ether
f
1. NaBH4
j
Mg / dry ether
2 H3O+
2. H3O+
C
PBг3
g
HOCH2CH2OH/HCI
k
H2/Pd
d
m-chloroperbenzoic
h
H3O+ / heat
1
CrO3 / H3O+
acid
a) 2-phenylcyclohexanone
b) cyclohexylbenzene
m
cyclohexanone
Transcribed Image Text:How would you synthesize the following compounds from cyclohexanone using reagents from the table? Use letters from the table to list reagents in the order used (first at the left). Reagents a 1. CH3MgBr / dry ether 2 H3O+ e 1. OsO4 i 1. BH3/THF 2. NaHSO3/H₂O 2. H₂O₂ / NaOH b 1. C6H5 MgBr / dry ether f 1. NaBH4 j Mg / dry ether 2 H3O+ 2. H3O+ C PBг3 g HOCH2CH2OH/HCI k H2/Pd d m-chloroperbenzoic h H3O+ / heat 1 CrO3 / H3O+ acid a) 2-phenylcyclohexanone b) cyclohexylbenzene m cyclohexanone
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