8th Edition

ISBN: 9780134066639

Author: Bruice

Publisher: PEARSON

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Chapter 9, Problem 119P

cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they react with HO^–.

Chapter 9, Problem 119P, cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a

a. Why do they form the same elimination product?

h. Explain, by showing the mechanisms, why different substitution products are obtained.

c. How many stereoisomers does each or the elimination and substitution reactions form?

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Chapter 9, Problem 118P

Chapter 9, Problem 120P

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cis-4-Bromocyclohexanol and trans-4-bromocyclohexanol form the same elimination product but a different substitution product when they reactwith HO-. a. Why do they form the same elimination product?b. Explain, by showing the mechanisms, why different substitution products are obtained.c. How many stereoisomers does each of the elimination and substitution reactions form?

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Draw all of the substitution and elimination products formed from thegiven alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate thestereochemistry around the stereogenic centers present in the products,as well as the mechanism by which each product is formed.

Chapter 9 Solutions

Organic Chemistry (8th Edition)

Ch. 9.1 - Prob. 3P Ch. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8P Ch. 9.2 - Prob. 9P Ch. 9.2 - Prob. 10P Ch. 9.2 - Prob. 11P Ch. 9.2 - Prob. 12P Ch. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P

Ch. 9.2 - Prob. 17P Ch. 9.3 - Prob. 18P Ch. 9.4 - Prob. 19P Ch. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22P Ch. 9.7 - Prob. 23P Ch. 9.7 - Prob. 24P Ch. 9.7 - Prob. 25P Ch. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28P Ch. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30P Ch. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33P Ch. 9.10 - Prob. 35P Ch. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38P Ch. 9.12 - Prob. 39P Ch. 9.12 - Prob. 40P Ch. 9.12 - Prob. 41P Ch. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44P Ch. 9.13 - Prob. 45P Ch. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47P Ch. 9.13 - Prob. 48P Ch. 9.13 - Prob. 49P Ch. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54P Ch. 9.14 - Prob. 55P Ch. 9.14 - Prob. 56P Ch. 9.14 - Prob. 58P Ch. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62P Ch. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65P Ch. 9.17 - Prob. 66P Ch. 9 - Prob. 1P Ch. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67P Ch. 9 - Prob. 68P Ch. 9 - Prob. 69P Ch. 9 - Prob. 70P Ch. 9 - Prob. 71P Ch. 9 - Prob. 72P Ch. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74P Ch. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76P Ch. 9 - Prob. 77P Ch. 9 - Prob. 78P Ch. 9 - Prob. 79P Ch. 9 - Prob. 80P Ch. 9 - Prob. 81P Ch. 9 - Prob. 82P Ch. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84P Ch. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86P Ch. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88P Ch. 9 - Prob. 89P Ch. 9 - Prob. 90P Ch. 9 - Prob. 91P Ch. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94P Ch. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97P Ch. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100P Ch. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105P Ch. 9 - Prob. 106P Ch. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108P Ch. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110P Ch. 9 - Prob. 111P Ch. 9 - Prob. 112P Ch. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115P Ch. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120P Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122P Ch. 9 - Prob. 123P Ch. 9 - Prob. 124P Ch. 9 - Prob. 125P Ch. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127P Ch. 9 - Prob. 128P Ch. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130P Ch. 9 - The reaction of chloromethane with hydroxide ion...

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Solution Summary: The author explains the reason for cis and trans- 4-bromocyclohexanol's same elimination product when reacting with HO-.

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Chapter 9 Solutions