ORGANIC CHEMISTRY-PRINT COMPANION (LL)
3rd Edition
ISBN: 9781119444251
Author: Klein
Publisher: WILEY
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Chapter 11, Problem 34IP
Interpretation Introduction
Interpretation:
A multi-step synthesis of 1-penten-3-ol using acetylene as only source of carbon atoms has to be given.
Concept Introduction:
Catalytic hydrogenation: It is the addition of molecular hydrogen across triple bond in presence of Lindlar’s catalyst. This catalyst stops hydrogenation to
Ozonolysis: It involves breaking of alkene double bond and addition of oxygen atoms to form carbonyl compounds.
Hydro-halogenation reaction: In this reaction, hydrogen halide added across the unsaturated bond (alkene).
Markovnikov’s rule: An unsymmetrical alkene reacts with hydrogen halide in which halide ions goes to the more substitution position of carbon-carbon double bond which provides
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Propose syntheses of the following compounds starting with benzene or toluene. Assume ortho and
isomers can be separated.
a.
b.
O₂N-
Cl
COOH
para
0. Propose syntheses to carry out each of the following conversions. Assume ortho and para isomers can
be separated
a.
Br
b.
COOH
CH3
NH₂
PABA
(active ingredient in some sunscreens)
H3C
H
C=C
CH3
H
m-chloroperoxybenzoic acid
CH2Cl2, rt
C-C--.
H3CH2CC
H
H3C CH3
Cl₂
H₂O
NaOH
H₂O
D.
S-
E.
CH3
H₂O₂, H₂O
It
CH₂O Na
+
CHI
F.
HI, H₂O
heat
G.
4
OH
CH3CHCH3 + ICH2CH3
1. NaH
(CH3)3COH
(CH3)3 COCHCH2CH3
2.
CH3
5. Show how the ether below could be prepared from toluene and any other necessary reagents. Show all
reagents and all intermediate structures.
H3C-
H3C-
CI
OCH2CH3
Chapter 11 Solutions
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
Ch. 11.1 - Prob. 1CCCh. 11.1 - Prob. 2CCCh. 11.2 - Prob. 1LTSCh. 11.2 - Prob. 3PTSCh. 11.2 - Prob. 4ATSCh. 11.3 - Prob. 2LTSCh. 11.3 - Prob. 5PTSCh. 11.3 - As we will see in Chapter 26, steroids are a class...Ch. 11.4 - Prob. 3LTSCh. 11.4 - Prob. 7PTS
Ch. 11.4 - Prob. 8ATSCh. 11.5 - Prob. 4LTSCh. 11.5 - Prob. 9PTSCh. 11.5 - Prob. 10ATSCh. 11 - Prob. 11PPCh. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Prob. 19PPCh. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Prob. 25PPCh. 11 - Prob. 26PPCh. 11 - Prob. 27IPCh. 11 - Prob. 28IPCh. 11 - Prob. 29IPCh. 11 - Prob. 30IPCh. 11 - Prob. 31IPCh. 11 - In a study of volatile compounds extracted from...Ch. 11 - Kakkon is the root of an Asian plant that has...Ch. 11 - Prob. 34IPCh. 11 - Prob. 35IPCh. 11 - Prob. 37IPCh. 11 - The aroma, taste, and general quality of wine are...Ch. 11 - Prob. 39CPCh. 11 - Prob. 40CPCh. 11 - Prob. 42CPCh. 11 - Prob. 43CP
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