Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 11.7C, Problem 11.15P
Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.
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Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo2-methylbutane, a rearranged product. Propose a mechanism for the formation of thisproduct.
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Chapter 11 Solutions
Organic Chemistry (9th Edition)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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- Solvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, ArSO3H. A sulfonic acid is a strong acid, and its anion, ArSO3, is a weak base and a good leaving group. Propose a mechanism for this reaction.arrow_forwardIn light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.arrow_forward1,4-Dioxane is made commercially by the acid-catalyzed condensation of an alcohol. Propose a mechanism for this reaction.arrow_forward
- When 3-methylbutan-2-ol is treated with concentrated HBr, the major product is 2-bromo-2-methylbutane. Propose a mechanism for the formation of this product.arrow_forwardThe reaction of 2,2-dimethyl-1-propanol with HBr is very slow and forms 2-bromo-2-methylbutane as the main product Propose a mechanism to explain these observationsarrow_forwardWhen 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.arrow_forward
- 1. Methylene cyclohexane, on treatment with strong acid, isomerises to yield methyl cyclohexene. Propose a mechanism by which the reaction might occur.arrow_forward2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.arrow_forwardAcid-catalyzed dehydration of neopentyl alcohol, (CH3)3CCH2OH, yields 2-methyl-2- butene as the major product. Outline a mechanism showing all steps in its formation.arrow_forward
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