An efficient synthesis that can be used to achieve each of the following transformations is to be determined. Concept introduction : The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

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Answer 1

Question

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

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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 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

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Answer 3

Question

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

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Answer 4

Question

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

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Answer 5

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

Answer 6

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

Answer 7

Chapter 12.13, Problem 27PTS

(a)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The product molecule has one more carbon atom than the starting material. For the generation of tertiary alcohol from secondary alcohol, there must be oxidation of alcohol to the carbonyl group, after which, there must be an addition of a methyl fragment, preferably using a Grignard reagent. This after hydrolysis can yield the desired tertiary alcohol.

Answer 8

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

Answer 9

(b)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction: The final product has one more carbon atom than the starting material. This can be facilitated by the addition of a methyl group, preferably using a Grignard reagent after conversion of alkyne to a carbonyl compound. The Grignard intermediate then can be hydrolyzed to obtain the final product.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve the following transformation is to be determined.

Concept introduction:

The final product contains two additional carbon atoms, so the synthesis requires a carbon-carbon bond-forming reaction. To facilitate this, the desired product should be produced by oxidizing the generated alcohol using the proper Grignard reagent.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains one additional carbon atom, so the synthesis must have a carbon-carbon bond-forming reaction. This can be achieved by using a Grignard reagent followed by an elimination reaction which can yield the desired unsaturated product.

Answer 14

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

Answer 15

(e)

Interpretation Introduction

Interpretation:

The efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule contains three additional carbon atoms, so the reaction needs a Carbon−Carbon bond-forming reaction. The alkyl halide can be first treated with magnesium metal to produce a Grignard reagent, followed by a reaction with the required ketone (acetone). It can then be converted to the desired product by treatment with thionyl chloride.

Answer 16

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

Answer 17

(f)

Interpretation Introduction

Interpretation:

An efficient synthesis that can be used to achieve each of the following transformations is to be determined.

Concept introduction:

The target molecule has two additional phenyl groups, which can be done by adding Grignard reagent containing phenyl groups two times, followed by oxidation. The starting material contains carbonyl carbon which is the reaction center for the phenyl part of the Grignard reagent.

Answer 18

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Answer 19

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Answer 20

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Answer 21

Ch. 12.1 - Prob. 1LTS Ch. 12.1 - Prob. 1PTS Ch. 12.1 - Prob. 2ATS Ch. 12.1 - Prob. 3CC Ch. 12.2 - Prob. 4CC Ch. 12.3 - Prob. 8CC Ch. 12.3 - Prob. 9CC Ch. 12.4 - Prob. 3LTS Ch. 12.4 - Prob. 10PTS Ch. 12.4 - Prob. 11ATS

Solution Summary: The author describes an efficient synthesis that can be used to achieve each of the following transformations.

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