a) Interpretation: How to carry out the selective transformation of a ketoaldehyde to ketoalcohol is to be shown. Concept introduction: Both aldehyde and keto groups are reduced by LiAlH 4 . In order to selectively reduce the aldehyde, the keto group is first protected by converting it into an acetal. The protected aldehyde can be reduced to a primary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids. To show: How to carry out the selective transformation of a ketoaldehyde to ketoalcohol.

Question

How might you carry out the following selective transformations? (Note that a protection step may be required, and recall that aldehydes are more reactive than ketones toward nucleophilic addition.)

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 61AP

Interpretation Introduction

a)

Interpretation:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce the aldehyde, the keto group is first protected by converting it into an acetal. The protected aldehyde can be reduced to a primary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol.

Interpretation Introduction

b)

Interpretation:

How to carry out the selective transformation of a diketone to an aldol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce one keto group, the other keto group is first protected by converting it into an acetal. The protected ketone can be reduced to a secondary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a diketone to an aldol.

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Students have asked these similar questions

How might you carry out the following selective transformations? (Note that a protection step may be required, and recall that aldehydes are more reactive than ketones toward nucleophilic addition.)

How would you carry out the following transformation? Tell what reagents you would use in each case.

What reagents should be used to carry out the following syntheses?

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 61AP

Interpretation Introduction

a)

Interpretation:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce the aldehyde, the keto group is first protected by converting it into an acetal. The protected aldehyde can be reduced to a primary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol.

Interpretation Introduction

b)

Interpretation:

How to carry out the selective transformation of a diketone to an aldol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce one keto group, the other keto group is first protected by converting it into an acetal. The protected ketone can be reduced to a secondary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a diketone to an aldol.

Expert Solution & Answer

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See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 61AP

Interpretation Introduction

a)

Interpretation:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce the aldehyde, the keto group is first protected by converting it into an acetal. The protected aldehyde can be reduced to a primary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a ketoaldehyde to ketoalcohol.

Interpretation Introduction

b)

Interpretation:

How to carry out the selective transformation of a diketone to an aldol is to be shown.

Concept introduction:

Both aldehyde and keto groups are reduced by LiAlH₄. In order to selectively reduce one keto group, the other keto group is first protected by converting it into an acetal. The protected ketone can be reduced to a secondary alcohol by reduction. The acetal can be removed by hydrolysis with dilute acids.

To show:

How to carry out the selective transformation of a diketone to an aldol.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 19.SE, Problem 61AP

Interpretation Introduction