The product of the reaction is to be predicted in which Phenylethanal is added slowly to a basic solution of Dimethylpropanal . Concept introduction: The reaction is a crossed aldol reaction. The base will deprotonate one aldehyde, and the resulting enolate anion will attack another aldehyde. As we have two aldehydes , base deprotonates the aldehyde with α-H . Dimethylpropanal has no α- hydrogens, so it cannot form enolate anion. Phenylethanal has α- hydrogens, so it forms the enolate nucleophile. Because Phenylethanal is added slowly, there is never a substantial concentration of it in its uncharged form, so the major reaction occurs between Phenylethanal enolate anion and Dimethylpropanal . Enolate anion undergoes nucleophilic addition with Dimethylpropanal and forms an aldol product. If an aldehyde with α- hydrogens is added slowly to a basic solution of an aldehyde without α- hydrogens, primarily one aldol product is formed. Because the reaction is heated, dehydration leads to the condensation product.

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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 18, Problem 18.28P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted in which Phenylethanal is added slowly to a basic solution of Dimethylpropanal.

Concept introduction:

The reaction is a crossed aldol reaction. The base will deprotonate one aldehyde, and the resulting enolate anion will attack another aldehyde. As we have two aldehydes, base deprotonates the aldehyde with α-H. Dimethylpropanal has no α- hydrogens, so it cannot form enolate anion. Phenylethanal has α- hydrogens, so it forms the enolate nucleophile. Because Phenylethanal is added slowly, there is never a substantial concentration of it in its uncharged form, so the major reaction occurs between Phenylethanal enolate anion and Dimethylpropanal. Enolate anion undergoes nucleophilic addition with Dimethylpropanal and forms an aldol product. If an aldehyde with α- hydrogens is added slowly to a basic solution of an aldehyde without α- hydrogens, primarily one aldol product is formed. Because the reaction is heated, dehydration leads to the condensation product.

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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 18, Problem 18.28P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted in which Phenylethanal is added slowly to a basic solution of Dimethylpropanal.

Concept introduction:

The reaction is a crossed aldol reaction. The base will deprotonate one aldehyde, and the resulting enolate anion will attack another aldehyde. As we have two aldehydes, base deprotonates the aldehyde with α-H. Dimethylpropanal has no α- hydrogens, so it cannot form enolate anion. Phenylethanal has α- hydrogens, so it forms the enolate nucleophile. Because Phenylethanal is added slowly, there is never a substantial concentration of it in its uncharged form, so the major reaction occurs between Phenylethanal enolate anion and Dimethylpropanal. Enolate anion undergoes nucleophilic addition with Dimethylpropanal and forms an aldol product. If an aldehyde with α- hydrogens is added slowly to a basic solution of an aldehyde without α- hydrogens, primarily one aldol product is formed. Because the reaction is heated, dehydration leads to the condensation product.

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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 18, Problem 18.28P

Interpretation Introduction

Interpretation:

The product of the reaction is to be predicted in which Phenylethanal is added slowly to a basic solution of Dimethylpropanal.

Concept introduction:

The reaction is a crossed aldol reaction. The base will deprotonate one aldehyde, and the resulting enolate anion will attack another aldehyde. As we have two aldehydes, base deprotonates the aldehyde with α-H. Dimethylpropanal has no α- hydrogens, so it cannot form enolate anion. Phenylethanal has α- hydrogens, so it forms the enolate nucleophile. Because Phenylethanal is added slowly, there is never a substantial concentration of it in its uncharged form, so the major reaction occurs between Phenylethanal enolate anion and Dimethylpropanal. Enolate anion undergoes nucleophilic addition with Dimethylpropanal and forms an aldol product. If an aldehyde with α- hydrogens is added slowly to a basic solution of an aldehyde without α- hydrogens, primarily one aldol product is formed. Because the reaction is heated, dehydration leads to the condensation product.

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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 18, Problem 18.28P

Interpretation Introduction