The missing compounds A through G are to be supplied. Concept introduction: Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde . Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH 4 to produce D. PBr 3 then converts the -OH group to Br to produce E . The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Answer 1

Question

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Answer 2

Question

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Answer 3

Question

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Answer 4

Question

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

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Answer 5

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

Answer 6

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

Answer 7

Chapter 20, Problem 20.62P

Interpretation Introduction

Interpretation:

The missing compounds A through G are to be supplied.

Concept introduction:

Diisobutylaluminium hydride (DIBAH), a specialized reducing agent, reduces an ester to an aldehyde. Thus, A is produced by reducing the starting material to the aldehyde. Under the basic conditions, A reacts with a ketone B in an aldol condensation reaction. Lithium dialkylcuprate then undergoes a conjugate addition. This is followed by reduction with NaBH4 to produce D. PBr3 then converts the -OH group to Br to produce E. The next reaction is Gabriel synthesis. Gabriel synthesis produces a primary amine from a corresponding alkyl halide. Therefore, in the Gabriel synthesis involving E, the primary amine F is produced. F undergoes Hoffman elimination in the final step to produce G.

Answer 8

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Answer 11

Ch. 20 - Prob. 20.1P Ch. 20 - Prob. 20.2P Ch. 20 - Prob. 20.3P Ch. 20 - Prob. 20.4P Ch. 20 - Prob. 20.5P Ch. 20 - Prob. 20.6P Ch. 20 - Prob. 20.7P Ch. 20 - Prob. 20.8P Ch. 20 - Prob. 20.9P Ch. 20 - Prob. 20.10P

Solution Summary: The author explains how the reducing agent Diisobutylaluminium hydride (DIBAH) reduces an ester to an aldehyde.

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