The synthesis of 2-methylcyclopentanone from cyclohexene is to be devised. Concept introduction: In the presence of ozone and CH 3 SCH 3 , oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH 3 SCH 3 . Dieckmann condensation reaction is a intramolecular condensation reaction in diester. In Dieckmann condensation reaction, the base abstracts the acidic proton from α carbon atom of one ester group to form enolate. This enolate reacts with carbonyl compound of other ester that leads to the formation of β -ketoester.

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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, Problem 63P

Interpretation Introduction

Interpretation: The synthesis of 2-methylcyclopentanone from cyclohexene is to be devised.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

Dieckmann condensation reaction is a intramolecular condensation reaction in diester. In Dieckmann condensation reaction, the base abstracts the acidic proton from α carbon atom of one ester group to form enolate. This enolate reacts with carbonyl compound of other ester that leads to the formation of β-ketoester.

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Devise a synthesis of each substituted cyclopropane. Use acetylene (HC≡CH) as a starting material in part (a), and cyclohexanone as a starting material in part (b). You may use any other organic compounds and any needed reagents.

Synthesize the following compound from cyclohexanone and any other organic and inorganic reagents you need.

Provide stepwise synthesis show all reagents need and intermediates formed along the way

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, Problem 63P

Interpretation Introduction

Interpretation: The synthesis of 2-methylcyclopentanone from cyclohexene is to be devised.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

Dieckmann condensation reaction is a intramolecular condensation reaction in diester. In Dieckmann condensation reaction, the base abstracts the acidic proton from α carbon atom of one ester group to form enolate. This enolate reacts with carbonyl compound of other ester that leads to the formation of β-ketoester.

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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, Problem 63P

Interpretation Introduction

Interpretation: The synthesis of 2-methylcyclopentanone from cyclohexene is to be devised.

Concept introduction: In the presence of ozone and CH3SCH3, oxidative cleavage occurs. In oxidative cleavage both the sigma and pi bond of the alkene is broken and two carbonyl compounds are formed. When ozone is added to the alkene, unstable intermediate molozonide is formed which rearranges to ozonide. This ozonide is reduced to form two carbonyl compounds in presence of CH3SCH3.

Dieckmann condensation reaction is a intramolecular condensation reaction in diester. In Dieckmann condensation reaction, the base abstracts the acidic proton from α carbon atom of one ester group to form enolate. This enolate reacts with carbonyl compound of other ester that leads to the formation of β-ketoester.

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Answer 4

Question

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, Problem 63P

Interpretation Introduction