Given that the compound shown, initially formed as the product in a Claisen rearrangement, is not usually isolated as it tautomerizes to its enol form. The structure of the enol is to be given and why the enol tautomer is favored is to be explained. Concept introduction: According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized π electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. π electrons will be aromatic and stable. Thus cyclic compounds with 4, 8, 12 etc, π electrons will be antiaromatic and less stable. To give: The structure of the enol formed by the tautomerization of the product of a Claisen rearrangement shown. To explain: Why the ketone obtained is not isolated and the enol form favored.

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Answer 1

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Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 55AP

Interpretation Introduction

Interpretation:

Given that the compound shown, initially formed as the product in a Claisen rearrangement, is not usually isolated as it tautomerizes to its enol form. The structure of the enol is to be given and why the enol tautomer is favored is to be explained.

Concept introduction:

According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized π electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. π electrons will be aromatic and stable. Thus cyclic compounds with 4, 8, 12 etc, π electrons will be antiaromatic and less stable.

To give:

The structure of the enol formed by the tautomerization of the product of a Claisen rearrangement shown.

To explain:

Why the ketone obtained is not isolated and the enol form favored.

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Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?

Answer 2

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 55AP

Interpretation Introduction

Interpretation:

Given that the compound shown, initially formed as the product in a Claisen rearrangement, is not usually isolated as it tautomerizes to its enol form. The structure of the enol is to be given and why the enol tautomer is favored is to be explained.

Concept introduction:

According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized π electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. π electrons will be aromatic and stable. Thus cyclic compounds with 4, 8, 12 etc, π electrons will be antiaromatic and less stable.

To give:

The structure of the enol formed by the tautomerization of the product of a Claisen rearrangement shown.

To explain:

Why the ketone obtained is not isolated and the enol form favored.

Expert Solution & Answer

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Check out a sample textbook solution

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Answer 3

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 55AP

Interpretation Introduction

Interpretation:

Given that the compound shown, initially formed as the product in a Claisen rearrangement, is not usually isolated as it tautomerizes to its enol form. The structure of the enol is to be given and why the enol tautomer is favored is to be explained.

Concept introduction:

According to Huckel’s rule, any specie that is cyclic, planar and has (4n+2) delocalized π electrons will be aromatic and stable. Thus species with 2, 6, 10, 14 etc. π electrons will be aromatic and stable. Thus cyclic compounds with 4, 8, 12 etc, π electrons will be antiaromatic and less stable.

To give:

The structure of the enol formed by the tautomerization of the product of a Claisen rearrangement shown.

To explain:

Why the ketone obtained is not isolated and the enol form favored.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Rule that estimates whether a given organic planar ring structure will show an aromatic property. A cyclic ring molecule is said to follow Hückel’s rule if the л-electrons count in a molecule is [4n+2], where n stands for a positive numerical value. It is also called the [4n+2] rule. Hückel's rule, sometimes referred to as the aromaticity rule, is one but not the only criteria to judge a molecule for aromaticity.

Chapter 15.SE, Problem 55AP

Interpretation Introduction