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.

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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 17.3, 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.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE

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Answer 2

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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 17.3, 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.

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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 17.3, 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

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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 17.3, Problem 8P

Interpretation Introduction