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

2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.

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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2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.

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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

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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

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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