EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Below is a structure of Levonorgestrel (Plan B®), used in prevention of pregancy.
но
HH
H.
Levonorgestrel Plan B®
Below is one of the reactions used in the synthesis. What type of reaction is it?
он
:CEC-H
Lc=c-H
THF as solvent
Levonorgestrel
H,CO
H,CO
O A grignard reaction.
Nucleophilic acyl substitution.
O Nucleophilic addition.
O An SN2 reaction.
O O
Identify the best reagents to complete the following reaction.
1
HO
8
A
B
O
D
E
LIAIH4
DMP (Dess-Martin Periodinane)
mCPBA
1. KMnO4, NaOH
2. Neutralizing work-up
PCC
W
Submit
1
How would you synthesize the following compounds from butanoic acid using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Example: ab
a
b
C
d
1. NaBH4
2. H3O+
1. LiAlH4
2. H30*
H₂/Pt
1. BH3/THF
2. H₂O₂/NaOH
a) 1-bromobutane
b) pentanoic acid
e
f
g
h
i
Reagents
PBr3
Mg/ dry ether
1. Li 2. Cul
1-bromobutane
H3O*, heat
j
k
I
m
n
KOH / alcohol
KOtBu
1. CO₂ 2. H3O+
HBr, dark
no peroxides
NaCN
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