How would you synthesize the following substances from benzaldehyde and reagents from the table? In general, the fewer the steps, the better the synthesis. You should not need more than four steps. Use letters from the table to list reagents in the order used (first at the left) with no commas. Example: cag Reagents a CH2=O f 1. CH3MgBr/dry ether 2 H3O+ j 1. P(C6H5)3 2. BuLi b g Dess-Martin periodinane in CH2Cl2 k Br2 C (C6H5)3P+-CH2 h 1. NaBH4 I PBг3 2. H3O+ m d NH + acid i 1. BH3/THF NaNH2/NH3 2. H2O2/NaOH e CrO3/H3O+ n Mg/ dry ether a) CH2CHO OH b)

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.38P
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How would you synthesize the following substances from benzaldehyde and
reagents from the table? In general, the fewer the steps, the better the
synthesis. You should not need more than four steps.
Use letters from the table to list reagents in the order used (first at the left)
with no commas.
Example: cag
Reagents
a
CH2=O
f
1. CH3MgBr/dry ether
2 H3O+
1. P(C6H5)3
2. BuLi
b
g
Dess-Martin periodinane
k
Br2
in CH2Cl2
C
(C6H5)3P+-CH2
h
1. NaBH4
I
PBr3
2. H3O+
m
d
NH + acid
i
1. BH3/THF
NaNH2/NH3
2. H2O2/NaOH
e
CrO3/H3O+
n
Mg / dry ether
a)
CH2CHO
OH
b)
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Transcribed Image Text:How would you synthesize the following substances from benzaldehyde and reagents from the table? In general, the fewer the steps, the better the synthesis. You should not need more than four steps. Use letters from the table to list reagents in the order used (first at the left) with no commas. Example: cag Reagents a CH2=O f 1. CH3MgBr/dry ether 2 H3O+ 1. P(C6H5)3 2. BuLi b g Dess-Martin periodinane k Br2 in CH2Cl2 C (C6H5)3P+-CH2 h 1. NaBH4 I PBr3 2. H3O+ m d NH + acid i 1. BH3/THF NaNH2/NH3 2. H2O2/NaOH e CrO3/H3O+ n Mg / dry ether a) CH2CHO OH b) Submit Answer Try Another Version 3 item attempts remaining
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