Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134066639
Author: Bruice
Publisher: PEARSON
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Chapter 9, Problem 67P

(a)

Interpretation Introduction

Interpretation:

Products formed when 1-bromopropane reacts with following nucleophile is to be identified.

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

(b)

Interpretation Introduction

Interpretation:

Products formed when 1-bromopropane reacts with following nucleophile is to be identified.

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

Steric effect is the effect due to the groups occupies a certain volume of space.

Steric hindrance is caused by the bulky groups at the site of a reaction that makes it difficult for the reactants to approach each other.

(c)

Interpretation Introduction

Interpretation:

Products formed when 1-bromopropane reacts with following nucleophile is to be identified.

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

Aprotic solvent are polar solvent molecules which do not have hydrogen bonded to oxygen to nitrogen.

Protic solvent are polar solvent molecules which do have hydrogen bonded to oxygen to nitrogen.

The stronger base is always a better nucleophile in an aprotic solvent.

(d)

Interpretation Introduction

Interpretation:

Products formed when 1-bromopropane reacts with following nucleophile is to be identified.

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

The stronger base is always a better nucleophile in an aprotic solvent.

(e)

Interpretation Introduction

Interpretation:

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

(f)

Interpretation Introduction

Interpretation:

Products formed when 1-bromopropane reacts with following nucleophile is to be identified.

Concept Introduction:

The SN2 reaction is a type of reaction mechanism in which one bond is broken and one bond is formed i.e., in one step. SN2 is a kind of nucleophilic substitution reaction mechanism.

The nucleophile attacks the back side of the carbon that is attached to the halogen. Therefore it takes an inversion of configuration.

The configuration of the product is inverted relative to the configuration of the reactant.

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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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