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Chapter 14, Problem 14.47AP

(a)

Interpretation Introduction

Interpretation:

The alkene should be identified from the dehydration of given alcohol.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  1

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  2

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction.

(b)

Interpretation Introduction

Interpretation:

The alkene should be identified from the dehydration of given alcohol.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  3

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  4

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction.

(c)

Interpretation Introduction

Interpretation:

The alkene should be identified from the dehydration of given alcohol.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  5

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  6

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction.

(d)

Interpretation Introduction

Interpretation:

The alkene should be identified from the dehydration of given alcohol.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  7

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  8

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction.

(e)

Interpretation Introduction

Interpretation:

The alkene should be identified from the dehydration of given alcohol.

Concept introduction:

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  9

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (H+) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e, Chapter 14, Problem 14.47AP , additional homework tip  10

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction.

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Chapter 14 Solutions

Fundamentals Of General, Organic, And Biological Chemistry Volume 1 Second Custom Edition For Washington State University, 2/e

Ch. 14.4 - Prob. 14.8PCh. 14.4 - What alcohols yield the following alkenes as the...Ch. 14.4 - Prob. 14.10KCPCh. 14.4 - What products would you expect from oxidation of...Ch. 14.4 - Prob. 14.12PCh. 14.4 - Prob. 14.13KCPCh. 14.5 - Prob. 14.14PCh. 14.5 - Prob. 14.15PCh. 14.7 - Prob. 14.1CIAPCh. 14.7 - Prob. 14.2CIAPCh. 14.7 - Prob. 14.3CIAPCh. 14.7 - Prob. 14.16PCh. 14.8 - What disulfides would you obtain from oxidation of...Ch. 14.9 - Prob. 14.18PCh. 14.10 - Prob. 14.19PCh. 14.10 - Prob. 14.20PCh. 14.10 - Prob. 14.4CIAPCh. 14.10 - Prob. 14.5CIAPCh. 14.10 - Prob. 14.6CIAPCh. 14.10 - Prob. 14.7CIAPCh. 14 - Prob. 14.21UKCCh. 14 - Prob. 14.22UKCCh. 14 - Prob. 14.23UKCCh. 14 - Prob. 14.24UKCCh. 14 - Prob. 14.25UKCCh. 14 - How do alcohols, ethers, and phenols differ...Ch. 14 - What is the structural difference between primary,...Ch. 14 - Prob. 14.28APCh. 14 - Prob. 14.29APCh. 14 - The Taxane nucleus is shown here; it is the basis...Ch. 14 - Vitamin E has the structure shown. Identify the...Ch. 14 - Give systematic names for the following alcohols:...Ch. 14 - Give systematic names for the following compound...Ch. 14 - Draw structures corresponding to the following...Ch. 14 - Draw structures corresponding to the following...Ch. 14 - Prob. 14.36APCh. 14 - Locate the alcohol functional groups in the taxane...Ch. 14 - Prob. 14.38APCh. 14 - Prob. 14.39APCh. 14 - Prob. 14.40APCh. 14 - Prob. 14.41APCh. 14 - Prob. 14.42APCh. 14 - Prob. 14.43APCh. 14 - Assume that you have samples of the following two...Ch. 14 - Which of the following alcohols can undergo...Ch. 14 - The following alkenes can be prepared by...Ch. 14 - Prob. 14.47APCh. 14 - Prob. 14.48APCh. 14 - What alcohols would you oxidize to obtain the...Ch. 14 - Prob. 14.50APCh. 14 - What is the structural relationship between a...Ch. 14 - Prob. 14.52APCh. 14 - Prob. 14.53APCh. 14 - Prob. 14.54APCh. 14 - Prob. 14.55APCh. 14 - Prob. 14.56APCh. 14 - Prob. 14.57APCh. 14 - Identify the chiral center(s) in each of the...Ch. 14 - Are the following molecules chiral or achiral? If...Ch. 14 - Prob. 14.60CPCh. 14 - Prob. 14.61CPCh. 14 - 1-Propanol is freely soluble in water, 1-butanol...Ch. 14 - Prob. 14.63CPCh. 14 - Prob. 14.64CPCh. 14 - Prob. 14.65CPCh. 14 - Prob. 14.66CPCh. 14 - Prob. 14.67CPCh. 14 - Prob. 14.68CPCh. 14 - Prob. 14.69CPCh. 14 - Prob. 14.70CPCh. 14 - Prob. 14.71CPCh. 14 - Prob. 14.72CPCh. 14 - (a)Draw all possible cyclic C7H14O alcohol isomers...Ch. 14 - Prob. 14.74GPCh. 14 - Prob. 14.75GP
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