A mechanism for the given reaction has to be proposed. Concept introduction: The Michael addition of a ketone and enolate to an α , β - unsaturated ketone gives δ - diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ - diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.19, Problem 22.57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction has to be proposed.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Done 11:14 ⚫ worksheets.beyondlabz.com 5 (a). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 6 5 (b). Using the peak information you listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum. Draw this diagram on your own sheet of paper and attach the sketch of your drawing to this question. Question 7 6. Are there any differences between the spectra you obtained in Beyond Labz and the predicted spectra? If so, what were the differences? <

2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.19, Problem 22.57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction has to be proposed.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Answer 3

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.19, Problem 22.57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction has to be proposed.

Concept introduction:

The Michael addition of a ketone and enolate to an α,β- unsaturated ketone gives δ- diketone as a final product. When the conjugate addition takes place under strongly acidic or basic conditions then δ- diketone undergoes a spontaneous intramolecular aldol condensation followed by dehydration to form a six membered ring compound commonly known as cyclohexenone. This synthesis is called as the Robinson annulation.

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Answer 4

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Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 22.19, Problem 22.57P

Interpretation Introduction