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

C. Modified from book problem 19-59 To form the following products, you can combine an aldehyde or ketone with a Grignard reagent. Which aldehyde/ketone and Grignard reagent do you need to react to form each? You should draw your starting materials and reagents but don't need to draw a mechanism. (a) 2-Pentanol (b) 1-Butanol

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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C. Modified from book problem 19-59 To form the following products, you can combine an aldehyde or ketone with a Grignard reagent. Which aldehyde/ketone and Grignard reagent do you need to react to form each? You should draw your starting materials and reagents but don't need to draw a mechanism. (a) 2-Pentanol (b) 1-Butanol

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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

Trending nowThis is a popular solution!

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