ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
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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

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