The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH, are to be given. 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. The aldol formed dehydrates on heating to yield α, β-unsaturated aldehyde or ketone as the product. To give: The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH.

Question

What product would you expect from aldol cyclization of hexanediol in basic solution?

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 51AP

Interpretation Introduction

Interpretation:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH, are to be given.

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. The aldol formed dehydrates on heating to yield α, β-unsaturated aldehyde or ketone as the product.

To give:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH.

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What product would you expect from aldol cyclization of hexanediol in basic solution?

The intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield threecyclic D,E-unsaturated ketones. Give the threeproducts and suggest a mechanism for formingone of the products.

) Cinnamaldehyde is used in artificial cinnamon flavoring. Show how cinnamaldehydeis synthesized by a crossed aldol condensation followed by dehydration.H CHcinnamaldehyde C COH(b) Adding acetophenone slowly to a cold solution of LDA produces the enolate of acetophenone; but adding LDA slowly to a cold solution of acetophenone produces acondensation product. Show the reactions happening in each case, and explain why weobserve such different results

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 51AP

Interpretation Introduction

Interpretation:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH, are to be given.

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. The aldol formed dehydrates on heating to yield α, β-unsaturated aldehyde or ketone as the product.

To give:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH.

Expert Solution & Answer

Trending nowThis is a popular solution!

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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 51AP

Interpretation Introduction

Interpretation:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH, are to be given.

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. The aldol formed dehydrates on heating to yield α, β-unsaturated aldehyde or ketone as the product.

To give:

The structures of the two enone products obtained, in the approximate ratio of 9:1, when 2, 5-heptanedione undergoes intramolecular aldol condensation in the presence of aqueous NaOH.

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 51AP

Interpretation Introduction