OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Question
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
Ph3P-CHCH3
H₂C
H3C
Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to
an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine
oxide and an alkene.
CH3
00
+
The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as
butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene
X m
CH3
The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z
isomers)…
Propose a reaction starting material and reagents to prepare diphenyl sulfide in the laboratory. Show all the needed steps in the formation of the product
Chapter 29 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
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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