To explain the reason when a dilute solution of acetaldehyde is shaken with NaOD in D 2 O , only the methyl hydrogens are exchanged with deuterium but the hydrogen attached to carbonyl carbon is not. Concept introduction: When a ketone or aldehyde reacts with a base, it abstracts the alpha hydrogen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the p K a of the carbonyl compound. When acetaldehyde reacts with hydroxide ion, the product formed is water which is a stronger acid than the acetaldehyde. Therefore, the small amount of enolate ion is formed.

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 18.3, Problem 8P

Interpretation Introduction

Interpretation: To explain the reason when a dilute solution of acetaldehyde is shaken with NaOD in D2O, only the methyl hydrogens are exchanged with deuterium but the hydrogen attached to carbonyl carbon is not.

Concept introduction: When a ketone or aldehyde reacts with a base, it abstracts the alpha hydrogen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

When acetaldehyde reacts with hydroxide ion, the product formed is water which is a stronger acid than the acetaldehyde. Therefore, the small amount of enolate ion is formed.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Show work. don't give Ai generated solution

Don't used Ai solution

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 18.3, Problem 8P

Interpretation Introduction

Interpretation: To explain the reason when a dilute solution of acetaldehyde is shaken with NaOD in D2O, only the methyl hydrogens are exchanged with deuterium but the hydrogen attached to carbonyl carbon is not.

Concept introduction: When a ketone or aldehyde reacts with a base, it abstracts the alpha hydrogen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

When acetaldehyde reacts with hydroxide ion, the product formed is water which is a stronger acid than the acetaldehyde. Therefore, the small amount of enolate ion is formed.

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 18.3, Problem 8P

Interpretation Introduction

Interpretation: To explain the reason when a dilute solution of acetaldehyde is shaken with NaOD in D2O, only the methyl hydrogens are exchanged with deuterium but the hydrogen attached to carbonyl carbon is not.

Concept introduction: When a ketone or aldehyde reacts with a base, it abstracts the alpha hydrogen to form an enolate ion. The amount of carbonyl compound converted into an enolate ion depend on the pKa of the carbonyl compound.

When acetaldehyde reacts with hydroxide ion, the product formed is water which is a stronger acid than the acetaldehyde. Therefore, the small amount of enolate ion is formed.

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 18.3, Problem 8P

Interpretation Introduction