Student's Solutions Manual for Organic Chemistry

9th Edition

ISBN: 9780134160375

Author: Leroy G. Wade, Jan W. Simek

Publisher: PEARSON

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Textbook Question

Chapter 18.16, Problem 18.27P

In the mechanism for acetal hydrolysis shown, the ring oxygen atom was protonated first, the ring was cleaved, and then the methoxy group was lost. The mechanism could also be written to show the methoxy oxygen protonating and cleaving first, followed by ring cleavage. Draw this alternative mechanism.

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Chapter 18.16, Problem 18.26P

Chapter 18.16, Problem 18.28P

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Chapter 18 Solutions

Student's Solutions Manual for Organic Chemistry

Ch. 18.3 - Give the IUPAC name and (if possible) a common...Ch. 18.5D - NMR spectra for two compounds are given here,...Ch. 18.5D - Why were no products from the McLafferty...Ch. 18.5D - Use equations to show the fragmentation leading to...Ch. 18.5E - Prob. 18.5P Ch. 18.7D - Show how you would synthesize each compound from...Ch. 18.8 - Prob. 18.7P Ch. 18.9 - Predict the products of the following reactions....Ch. 18.9 - Show how the following transformations may be...Ch. 18.10 - Prob. 18.10P

Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12P Ch. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15P Ch. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17P Ch. 18.14 - Prob. 18.18P Ch. 18.14 - Prob. 18.19P Ch. 18.14 - Prob. 18.20P Ch. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22P Ch. 18.15 - Prob. 18.23P Ch. 18.16 - Prob. 18.24P Ch. 18.16 - Prob. 18.25P Ch. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28P Ch. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30P Ch. 18.18 - Prob. 18.31P Ch. 18.18 - Prob. 18.32P Ch. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35P Ch. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SP Ch. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SP Ch. 18 - Prob. 18.49SP Ch. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SP Ch. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SP Ch. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SP Ch. 18 - Prob. 18.64SP Ch. 18 - Prob. 18.65SP Ch. 18 - Prob. 18.66SP Ch. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SP Ch. 18 - Prob. 18.69SP Ch. 18 - Prob. 18.70SP Ch. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SP Ch. 18 - Prob. 18.75SP Ch. 18 - Prob. 18.76SP Ch. 18 - Prob. 18.77SP

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Solution Summary: The author explains that the alternative mechanism for acetal hydrolysis is to be stated.

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Chapter 18 Solutions