Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
Question
Chapter 7, Problem 43P
Interpretation Introduction

Interpretation:

The compound with the molecular formula C7H13Br thatyields the indicated alkene as the exclusive product of E2 elimination is to be predicted.

Concept introduction:

>

The alkyl halides, in the presence of a strong base, undergo dehydrohalogenation and formcorresponding alkenes.

>

In dehydrohalogenation H and X (halogen atom) areeliminated from adjacent carbons.

>

The elimination of primary alkyl halides proceeds through E2 mechanism.

>

In E2 mechanism, the attack of base and detachment of leaving group occurs simultaneously, and there is no carbocation formation step.

>

According to Zaitsev rule, the most substituted alkene is the major product.

Expert Solution & Answer
Check Mark

Answer to Problem 43P

Solution:

The compounds of molecular formula C7H13Br that gives each alkene shown as the exclusive product of E2 elimination are as follows:

a)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  1

b)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  2

c)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  3

d)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  4

e)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  5

f)

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  6

Explanation of Solution

a) The structure of the given alkene as the product of E2 elimination is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  7

In E2 mechanism, H and Br are eliminated from adjacent carbons and the double bond forms between those carbons to form an alkene.

Hence, the structure of alkyl bromide is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  8

b) The structure of the given alkene as the product of E2 elimination is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  9

In E2 mechanism, H and Br are eliminated from adjacent carbons and the double bond forms between those carbons to form an alkene.

So, there are two possible structures of alkyl bromide which are as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  10

The primary alkyl bromide forms the desired product but the tertiary alkyl bromide can form two alkenes with trisubstituted alkene as the major product. The reaction is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  11

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  12

Hence, the structure of the compound that forms the given alkene as an exclusive product of E2 elimination is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  13

c)The structure of given alkene as the product of E2 elimination is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  14

In E2 mechanism, H and Br are eliminated from adjacent carbons and the double bond forms between those carbons to form an alkene.

So, there are two possible structures of alkyl bromide as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  15

The alkyl bromide in which Br is placed at C-4 with respect to CH3, forms the desired product but the alkyl bromide in which Br is placed at C-3 with respect to CH3, forms two products.The reaction is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  16

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  17

Hence, the structure of the compound that forms the given alkene as an exclusive product of E2 elimination is:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  18

d) The structure of the given alkene as the product of E2 elimination is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  19

In E2 mechanism, H and Br are eliminated from adjacent carbons and the double bond forms between those carbons to form an alkene.

So, there are two possible structures of alkyl bromide as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  20

The primary alkyl bromide forms the desired product but the secondary alkyl bromide can form two alkenes with trisubstituted alkene as the major product.

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  21

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  22

Hence, the structure of the compound that forms the given alkene as an exclusive product of E2 elimination is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  23

e) The structural formula of the given alkene is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  24

In E2 mechanism, H and Br are eliminated from the adjacent carbons and the double bond forms between those carbons to form an alkene.

So, there are two possible structures of alkyl bromide as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  25

The alkyl bromide in which Br is placed at C-3 with respect to the isopropyl group forms the desired product but the alkyl bromide in which Br is placed at C-2 with respect to isopropyl forms two products.

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  26

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  27

Hence, the structure of the compound that forms the given alkene as an exclusive product of E2 elimination is

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  28

f) The structural formula of the given alkene is shown below:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  29

In E2 mechanism, H and Br are eliminated from adjacent carbons and the double bond forms between those carbons to form an alkene.

So, there are two possible structures of alkyl bromide as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  30

The secondary alkyl bromide forms two alkenesbut the tertiary alkyl bromide forms only the desired product as shown in following equations:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  31

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  32

Hence, the structure of the compound that forms the given alkene as an exclusive product of E2 elimination is as follows:

Organic Chemistry - Standalone book, Chapter 7, Problem 43P , additional homework tip  33

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Chapter 7 Solutions

Organic Chemistry - Standalone book

Ch. 7.6 - Standard enthalpies of formation are known for all...Ch. 7.6 - Prob. 12PCh. 7.6 - Despite numerous attempts, the alkene...Ch. 7.6 - Write structural formulas for the six isomeric...Ch. 7.7 - Place a double bond in the carbon skeleton shown...Ch. 7.9 - Identify the alkene obtained on dehydration of...Ch. 7.10 - Prob. 17PCh. 7.11 - Prob. 18PCh. 7.12 - Prob. 19PCh. 7.13 - The alkene mixture obtained on dehydration of...Ch. 7.14 - Write the structures of all the alkenes that can...Ch. 7.14 - Write structural formulas for all the alkenes that...Ch. 7.15 - A study of the hydrolysis behavior of...Ch. 7.15 - Use curved arrows to illustrate the electron flow...Ch. 7.15 - Predict the major product of the reaction shown.Ch. 7.16 - Prob. 26PCh. 7.17 - Prob. 27PCh. 7.18 - Prob. 28PCh. 7.19 - Predict the major organic product of each of the...Ch. 7.19 - A standard method for the synthesis of ethers is...Ch. 7 - Write structural formulas for each of the...Ch. 7 - Prob. 32PCh. 7 - Give an IUPAC name for each of the following...Ch. 7 - A hydrocarbon isolated from fish oil and from...Ch. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Choose the more stable alkene in each of the...Ch. 7 - Suggest an explanation for the fact that...Ch. 7 - Prob. 41PCh. 7 - Write structural formulas for all the alkene...Ch. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Predict the major organic product of each of the...Ch. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - The rate of the reaction In the first order in...Ch. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - You have available 2,2-dimethylcyclopentanol (A)...Ch. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Acid-catalyzed dehydration of...Ch. 7 - The ratio of elimination to substitution is...Ch. 7 - Prob. 57PCh. 7 - Prob. 58DSPCh. 7 - Prob. 59DSPCh. 7 - Prob. 60DSPCh. 7 - Prob. 61DSPCh. 7 - A Mechanistic Preview of Addition Reactions The...Ch. 7 - Prob. 63DSPCh. 7 - Prob. 64DSPCh. 7 - Prob. 65DSP
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