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.

Question

Want to see the full answer?

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Identifying electron-donating and For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene. Molecule Inductive Effects NH2 ○ donating NO2 Explanation Check withdrawing no inductive effects Resonance Effects Overall Electron-Density ○ donating O withdrawing O no resonance effects O donating O withdrawing O donating withdrawing O no inductive effects Ono resonance effects O electron-rich electron-deficient O similar to benzene O electron-rich O electron-deficient O similar to benzene olo 18 Ar 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibility

Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. Explanation Check Х (Choose one) OH (Choose one) OCH3 (Choose one) OH (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center

Assign R or S to all the chiral centers in each compound drawn below porat bg 9 Br Br

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Want to see the full answer?

Chapter 9 Solutions