(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.

Question

(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.

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 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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(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.

Give the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)

Explain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.

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