(a) Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn. Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone . In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β -ketoester.

Question

(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an OH group. 2-methylcyclohexanone

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional isomers that are not tautomers, but contain a C=C and an OH group. 2-methylcyclohexanone

Explain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.

(a) Draw the structure of the hemiacetal formed from one mole of benzaldehyde and one mole of ethanol. (b) Draw the structure of the acetal formed from one mole of benzaldehyde and two moles of ethanol. (c) Draw the structure of 2-methoxy-2-butanol. What compounds could you prepare this from? (d) Draw the structure of 3-methoxyl-2-butanol. What functional groups are present? Is this an acetal, a hemiacetal, or neither? Explain. (e) Identify the functional groups in the molecules shown below. Circle any acetals or hemiacetal, and identify which they are. 0-

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 59P

Interpretation Introduction

(a)

Interpretation: The stepwise mechanism for the reaction of ethyl hexa-2, 4-dienoate with diethyl oxalate in the presence of base is to be drawn.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(b)

Interpretation: An explanation regarding the formation of a new carbon-carbon bond on C6 with the help of mechanism is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

Interpretation Introduction

(c)

Interpretation: The reason as to why the given reaction is an example of a crossed Claisen reaction is to be stated.

Concept introduction: Claisen condensation takes place between two esters or between an ester and a ketone. In crossed Claisen condensation reaction, a base abstracts an acidic proton from an α carbon atom of carbonyl compound to form an enolate. This enolate reacts with carbonyl group of other carbonyl compounds that lead to the formation of β-ketoester.

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22, Problem 59P

Interpretation Introduction