Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 29, Problem 29.15P
Interpretation Introduction
Interpretation:
Reaction mechanism has to be proposed for the conversion of cyclohexanone to caprolactum.
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Caprolactam, the monomer from which nylon 6 is synthesized, is prepared from cyclo-
hexanone in two steps. In Step 1, cyclohexanone is treated with hydroxylamine to form
cyclohexanone oxime. Treatment of the oxime with concentrated sulfuric acid in Step 2
gives caprolactam by a reaction called a Beckmann rearrangement. Propose a mecha-
nism for the conversion of cyclohexanone oxime to caprolactam.
HO
NH
NH,OH
H,SO,
Cyclohexanone
Cyclohexanone
Сaprolactam
oxime
Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure
to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents
of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of
isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid,
HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid,
OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.
Structure of
product C
A hydrocarbon, A, with formula C11H16
undergoes hydrogenation with Pd to give
product B, C11H22, and with Lindlar's
catalyst to give product C, C11 H18.
Ozonolysis leads to a mixture of
products including cyclohexanone and
4-oxobutanoic acid. Treatment with
sodium amide (NaNH2) followed by
bromoethane gives compound D, C13H20.
Draw possible structures for A, B, C, and
D.
H₂,
Lindlar's
Problem 13 of 14
Structure of
A
1. NaNH2
Submit
2.
CH3CH₂Br
Structure of
product D
Chapter 29 Solutions
Organic Chemistry
Ch. 29.2 - Prob. 29.1PCh. 29.5 - Prob. 29.2PCh. 29.6 - Prob. AQCh. 29.6 - Prob. BQCh. 29.6 - Prob. CQCh. 29.6 - Prob. DQCh. 29.6 - Prob. EQCh. 29.6 - Prob. FQCh. 29.6 - Prob. 29.3PCh. 29.6 - Prob. 29.4P
Ch. 29 - Prob. 29.5PCh. 29 - Prob. 29.6PCh. 29 - Prob. 29.7PCh. 29 - Prob. 29.8PCh. 29 - Prob. 29.9PCh. 29 - Prob. 29.10PCh. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Prob. 29.13PCh. 29 - Prob. 29.14PCh. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 29 - Polycarbonates (Section 29.5C) are also formed by...Ch. 29 - Prob. 29.18PCh. 29 - Prob. 29.19PCh. 29 - Prob. 29.20PCh. 29 - Prob. 29.21PCh. 29 - Draw a structural formula of the polymer resulting...Ch. 29 - Prob. 29.23PCh. 29 - Prob. 29.24PCh. 29 - Prob. 29.25PCh. 29 - Select the monomer in each pair that is more...Ch. 29 - Prob. 29.27PCh. 29 - Prob. 29.28PCh. 29 - Prob. 29.29PCh. 29 - Prob. 29.30PCh. 29 - Prob. 29.31PCh. 29 - Prob. 29.32PCh. 29 - Prob. 29.33PCh. 29 - Radical polymerization of styrene gives a linear...Ch. 29 - Prob. 29.35PCh. 29 - Prob. 29.36PCh. 29 - Prob. 29.37PCh. 29 - Prob. 29.38P
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