(a) Interpretation: Synthesis of the given compound beginning with pentan-2-one is to be suggested. 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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

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Answer 1

Question

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

Highlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OH

Answer 2

Question

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

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Answer 3

Question

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

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Answer 4

Question

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

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Answer 5

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

Answer 6

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Answer 7

Chapter 19, Problem 19.43P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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 the reactants, and from retrosynthetic analysis, we can draw the synthesis of the target molecule.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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, and from the retrosynthetic analysis, we can draw the synthesis of the target molecule.

Answer 10

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

Answer 11

Interpretation Introduction

(c)

Interpretation:

Synthesis of the given compound beginning with pentan-2-one is to be suggested.

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. And from the retrosynthetic analysis we can draw the synthesis of the target molecule.

Answer 12

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Answer 14

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Answer 15

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 suggests a carbon–carbon bond-forming reaction for the given compound beginning with pentan-2-one.

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