(a) Interpretation: The structure of enolate formed by the treatment of 2 , 2 − dimethylcyclohexanone with LDA is to be stated. The aldol product of 2 , 2 − dimethylcyclohexanone with acetaldehyde is to be stated. Concept introduction: In aldol condensation reaction, the base abstracts an acidic proton from the carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of hydroxyaldehyde or hydroxyketone which on further dehydration gives the conjugated enone.

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Answer 1

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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 22, Problem 22.20P

Interpretation Introduction

(a)

Interpretation:

The structure of enolate formed by the treatment of 2,2−dimethylcyclohexanone with LDA is to be stated. The aldol product of 2,2−dimethylcyclohexanone with acetaldehyde is to be stated.

Concept introduction:

In aldol condensation reaction, the base abstracts an acidic proton from the carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of hydroxyaldehyde or hydroxyketone which on further dehydration gives the conjugated enone.

Interpretation Introduction

(b)

Interpretation:

Whether the diastereomers of the product are formed in equal or in different amounts is to be stated.

Concept introduction:

Diastereomers are the type of stereoisomers that are non identical, non super imposable mirror images of each other. Diastereomers can have different physical and chemical properties. They must have two stereocentes.

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Part II. two unbranched ketone have molecular formulla (C8H100). El-ms showed that both of them have a molecular ion peak at m/2 =128. However ketone (A) has a fragment peak at m/2 = 99 and 72 while ketone (B) snowed a fragment peak at m/2 = 113 and 58. 9) Propose the most plausible structures for both ketones b) Explain how you arrived at your conclusion by drawing the Structures of the distinguishing fragments for each ketone, including their fragmentation mechanisms.

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 22, Problem 22.20P

Interpretation Introduction

(a)

Interpretation:

The structure of enolate formed by the treatment of 2,2−dimethylcyclohexanone with LDA is to be stated. The aldol product of 2,2−dimethylcyclohexanone with acetaldehyde is to be stated.

Concept introduction:

In aldol condensation reaction, the base abstracts an acidic proton from the carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of hydroxyaldehyde or hydroxyketone which on further dehydration gives the conjugated enone.

Interpretation Introduction

(b)

Interpretation:

Whether the diastereomers of the product are formed in equal or in different amounts is to be stated.

Concept introduction:

Diastereomers are the type of stereoisomers that are non identical, non super imposable mirror images of each other. Diastereomers can have different physical and chemical properties. They must have two stereocentes.

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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 22, Problem 22.20P

Interpretation Introduction

(a)

Interpretation:

The structure of enolate formed by the treatment of 2,2−dimethylcyclohexanone with LDA is to be stated. The aldol product of 2,2−dimethylcyclohexanone with acetaldehyde is to be stated.

Concept introduction:

In aldol condensation reaction, the base abstracts an acidic proton from the carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of hydroxyaldehyde or hydroxyketone which on further dehydration gives the conjugated enone.

Interpretation Introduction

(b)

Interpretation:

Whether the diastereomers of the product are formed in equal or in different amounts is to be stated.

Concept introduction:

Diastereomers are the type of stereoisomers that are non identical, non super imposable mirror images of each other. Diastereomers can have different physical and chemical properties. They must have two stereocentes.

Expert Solution & Answer

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See solution

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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 22, Problem 22.20P

Interpretation Introduction