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.

Question

Want to see the full answer?

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 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

#1. Retro-Electrochemical Reaction: A ring has been made, but the light is causing the molecule to un- cyclize. Undo the ring into all possible molecules. (2pts, no partial credit) hv

Don't used Ai solution

I have a question about this problem involving mechanisms and drawing curved arrows for acids and bases. I know we need to identify the nucleophile and electrophile, but are there different types of reactions? For instance, what about Grignard reagents and other types that I might not be familiar with? Can you help me with this? I want to identify the names of the mechanisms for problems 1-14, such as Gilman reagents and others. Are they all the same? Also, could you rewrite it so I can better understand? The handwriting is pretty cluttered. Additionally, I need to label the nucleophile and electrophile, but my main concern is whether those reactions differ, like the "Brønsted-Lowry acid-base mechanism, Lewis acid-base mechanism, acid-catalyzed mechanisms, acid-catalyzed reactions, base-catalyzed reactions, nucleophilic substitution mechanisms (SN1 and SN2), elimination reactions (E1 and E2), organometallic mechanisms, and so forth."

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See 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 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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See 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 18, Problem 18.28P

Interpretation Introduction