Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 9, Problem 9.64P
Interpretation Introduction

(a)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  1

Explanation of Solution

The given reagent is HBr. Hydrogen bromide (HBr) is a strong acid.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  2

Figure 1

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 1.

Interpretation Introduction

(b)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  3

Explanation of Solution

The given reagent is H2O(H2SO4). Sulfuric acid (H2SO4) is a strong acid.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  4

Figure 2

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 2.

Interpretation Introduction

(c)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  5

Explanation of Solution

The given reagent is [1]CH3CH2O;[2]H2O. Ethoxide ion (CH3CH2O) is a strong nucleophile.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  6

Figure 3

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 3.

Interpretation Introduction

(d)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  7

Explanation of Solution

The given reagent is [1]HCC;[2]H2O. Acetylide ion (HCC) is a strong nucleophile.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  8

Figure 4

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 4.

Interpretation Introduction

(e)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  9

Explanation of Solution

The given reagent is [1]OH;[2]H2O. Hydroxyl ion (OH) is a strong nucleophile.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  10

Figure 5

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 5.

Interpretation Introduction

(f)

Interpretation: The product formed by the treatment of ethylene oxide with the given reagent is to be drawn.

Concept introduction: The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and the mechanism of the reaction with HZ is in between SN2andSN1.

Expert Solution
Check Mark

Answer to Problem 9.64P

The product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  11

Explanation of Solution

The given reagent is [1]CH3S;[2]H2O. Methyl sulfide ion (CH3S) is a strong nucleophile.

The opening of an epoxide/ethylene oxide ring is regioselective either it takes place with a strong nucleophile (:Nu) or an acid (HZ). The mechanism of the reaction with :Nu is SN2, and nucleophilic attack takes place at less substituted carbon atom. The mechanism of the reaction with HZ is in between SN2andSN1, and attack of Z takes place at highly substituted carbon atom.

Thus, the product formed by the treatment of ethylene oxide with the given reagent is,

Organic Chemistry, Chapter 9, Problem 9.64P , additional homework tip  12

Figure 6

Conclusion

The product formed by the treatment of ethylene oxide with the given reagent is drawn in Figure 6.

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Chapter 9 Solutions

Organic Chemistry

Ch. 9 - Problem 9.11 Draw the products formed when each...Ch. 9 - Prob. 9.12PCh. 9 - Problem 9.13 Draw the structure of each...Ch. 9 - What other alkene is also formed along with Y in...Ch. 9 - Prob. 9.15PCh. 9 - Explain why two substitution products are formed...Ch. 9 - Draw the products of each reaction. a. b. c.Ch. 9 - Problem 9.18 Draw the products of each reaction,...Ch. 9 - Problem 9.19 What is the major product formed...Ch. 9 - Prob. 9.20PCh. 9 - Prob. 9.21PCh. 9 - Problem 9.22 Draw the organic products formed in...Ch. 9 - Problem 9.23 Draw two steps to convert into each...Ch. 9 - Prob. 9.24PCh. 9 - Problem 9.25 Draw the products of each reaction,...Ch. 9 - Draw the products formed when (S)-butan-2-ol is...Ch. 9 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9 - What alkyl halides are formed when each ether is...Ch. 9 - Explain why the treatment of anisole with HBr...Ch. 9 - Name each thiol. a. b. Ch. 9 - Draw the product of each reaction. ac b.d.Ch. 9 - Give the IUPAC name for each sulfide. a. b. Ch. 9 - Draw the product of each reaction. a. b. Ch. 9 - Prob. 9.34PCh. 9 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 9.39PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 9.41PCh. 9 - Prob. 9.42PCh. 9 - Prob. 9.43PCh. 9 - 9.44 Why is the boiling point of higher than...Ch. 9 - 9.45 Draw the organic product(s) formed when is...Ch. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 9.47PCh. 9 - 9.48 Draw the products of each reaction and...Ch. 9 - 9.49 Draw the product of the following reaction,...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - 9.52 Draw a stepwise mechanism for the following...Ch. 9 - 9.53 Although alcohol V gives a single alkene W...Ch. 9 - Prob. 9.54PCh. 9 - Prob. 9.55PCh. 9 - Prob. 9.56PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.58PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 9.60PCh. 9 - 9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 9.64PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - When each halohydrin is treated with, a product of...Ch. 9 - Prob. 9.67PCh. 9 - Prob. 9.68PCh. 9 - Prob. 9.69PCh. 9 - Prob. 9.70PCh. 9 - Prepare each compound from cyclopentanol. More...Ch. 9 - 9.72 Identify the reagents (a–h) needed to carry...Ch. 9 - Prob. 9.73PCh. 9 - 9.74 Treatment of with affords compound A and ....Ch. 9 - Prob. 9.75PCh. 9 - Prob. 9.76PCh. 9 - 9.77 Draw a stepwise, detailed mechanism for the...Ch. 9 - 9.78 Dehydration of with affords as a minor...Ch. 9 - Prob. 9.79PCh. 9 - 9.80 Draw a stepwise mechanism for the following...Ch. 9 - 9.81 Aziridines are heterocycles that contain an...
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