Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 9, Problem 100P

(a)

Interpretation Introduction

Interpretation:

The structures of products obtained from the reaction of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol should be drawn.

Concept Introduction:

The SN reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step.SN is a kind of nucleophilic substitution reaction mechanism.

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

(b)

Interpretation Introduction

Interpretation:

The optically activity of products obtained from the reaction of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol should be explained.

Concept Introduction:

The SN reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN is a kind of nucleophilic substitution reaction mechanism.

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

(c)

Interpretation Introduction

Interpretation:

How would be the products differ if the starting material were the Trans isomer should be explained and the optical activity of products obtained from the Trans isomer should be explained.

Concept Introduction:

The SN reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN is a kind of nucleophilic substitution reaction mechanism.

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

(d)

Interpretation Introduction

Interpretation:

The rate of formation of substitution products should be comparatively explained, where the cis and Trans isomers of 1-chloro-2-isopropylcyclopentan of with sodium methoxide in methanol.

Concept Introduction:

The SN reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN is a kind of nucleophilic substitution reaction mechanism.

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

(e)

Interpretation Introduction

Interpretation:

The rate of formation of elimination products should be comparatively explained, where the cis and Trans isomers of 1-chloro-2-isopropylcyclopentan of with sodium methoxide in methanol.

Concept Introduction:

The SN reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN is a kind of nucleophilic substitution reaction mechanism.

An E2 reaction is a concerted, one-step reaction in which the proton and the halide ion are removed in the same step.

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a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium ethoxidein methanol.b. Are all the products optically active?c. How would the products differ if the starting material were the trans isomer? Are these products optically active?d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?
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Chapter 9 Solutions

Organic Chemistry (8th Edition)

Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 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. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 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. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 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. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 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. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 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. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 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. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 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. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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