(a) Interpretation: If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis. Concept introduction: The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

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Answer 1

Question

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

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3) Draw the structures of the major organic product(s) for the following reactions. HI in CH₂Cl₂ 3 excess Cl₂ in H₂O H₂SO4 in H₂O (Two products) Br-Cl in THF 1) BH3 2) alkaline H₂O₂ OSO4 + HOOH

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Answer 2

Question

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

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Answer 3

Question

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

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Answer 4

Question

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

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Answer 5

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 6

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 7

Chapter 19, Problem 19.42P

Interpretation Introduction

(a)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 8

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 9

Interpretation Introduction

(b)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 10

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 11

Interpretation Introduction

(c)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 12

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 13

Interpretation Introduction

(d)

Interpretation:

If the given compound must be synthesized using compounds with six or fewer carbons, it is to be determined which carbon–carbon bond-forming reaction from Table 19-1 should be incorporated in the synthesis.

Concept introduction:

The carbon–carbon bond-forming reaction results in heteroatoms having a specific relative positioning along the carbon backbone. If the heteroatoms in a target have 1, 2-, 1, 3-, 1, 4-, or 1, 5- relative positioning and the synthesis calls for a carbon–carbon bond-forming reaction, then consider using a corresponding reaction from Table 19-1. In a retrosynthetic analysis, therefore, apply a transform that takes our target molecule back to reactants. Disconnect the appropriate C-C bond to take back to reactants.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

Solution Summary: The author explains the carbon–carbon bond-forming reaction from Table 19-1 that can be incorporated in the synthesis.

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