The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen is to be explained. Concept introduction: Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule. To explain: The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen.

Question

Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction. (a) Trimethyl acetaldehyde (d) 3-Pentanone(b ) Cyclobutanone (e) Decanal(c) Benzophenone (diphenyl ketone) (f) 3-Phenyl-2-propenal

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 23.SE, Problem 54AP

Interpretation Introduction

Interpretation:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen.

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Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction. (a) Trimethyl acetaldehyde (d) 3-Pentanone(b ) Cyclobutanone (e) Decanal(c) Benzophenone (diphenyl ketone) (f) 3-Phenyl-2-propenal

Show the products from the reaction of p-bromoaniline with following reagents: a)CH3Cl(excess) b) HCl c) CH3COCl d) CH3MgBr e) CH3CH2Cl, AlCl3

How might you prepare this molecule using a nucleophilic displacement of an alkyl halide?

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 23.SE, Problem 54AP

Interpretation Introduction

Interpretation:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen.

Expert Solution & Answer

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See solution

Check out sample textbook 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 23.SE, Problem 54AP

Interpretation Introduction

Interpretation:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

The fact that 2, 2, 6-trimethylcyclohexanone yields no detectable aldol product even though it has an acidic α-hydrogen.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 23.SE, Problem 54AP

Interpretation Introduction