a) Interpretation: Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated. Concept introduction: A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH 2 Cl 2 /Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond. To state: Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

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Answer 1

Question

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

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Answer 2

Question

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

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Answer 3

Question

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

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Answer 4

Question

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

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Answer 5

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

Answer 6

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

Answer 7

Chapter 9.SE, Problem 16VC

Interpretation Introduction

a)

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

A cyclopropane ring is formed in Simmons-Smith reaction when an alkene is treated with CH₂Cl₂/Zn-Cu couple. Higher alkynes can be prepared by treating sodium acetylide with an alkyl bromide containing the required number of carbon atoms. Alkynes are reduced to alkenes by reduction with hydrogen in the presence of Lindlar catalyst. Alkenes when hydrated using oxymercuration-demercuration process yield an alcohol with OH group attached to a more highly substituted carbon atom in a double bond.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

Answer 8

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

Answer 9

b)

Interpretation Introduction

Interpretation:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared is to be stated.

Concept introduction:

The compound shown has a keto group at C₂ and a double bond between C₅ & C₆. The keto group can be introduced by hydration of an alkyne with aqueous H₂SO₄ in the presence of HgSO₄. An enol obtained during hydration upon tautomerization yields the ketone. The alkyne part can be introduced in to an alkene by treating a bromoalkene with the required number of carbon atoms with sodium actylide.

To state:

Starting from any compound having four or less number of carbon atoms how the compound shown can be prepared.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 9.1 - Prob. 1P Ch. 9.1 - Prob. 2P Ch. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4P Ch. 9.4 - Prob. 5P Ch. 9.4 - Prob. 6P Ch. 9.4 - Prob. 7P Ch. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P

Solution Summary: The author explains how the compound shown can be prepared by the route shown below starting from 3-bromo-1-propyne.

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Chapter 9 Solutions