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.

Question

Want to see the full answer?

Answer 1

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

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Q1: For each molecule, assign each stereocenter as R or S. Circle the meso compounds. Label each compound as chiral or achiral. OH HO CI Br H CI CI Br CI CI Xf x f g Br D OH Br Br H₂N R. IN Ill I -N S OMe D II H CO₂H 1/111 DuckDuckG

These are synthesis questions. You need to show how the starting material can be converted into the product(s) shown. You may use any reactions we have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. If a racemic molecule is made along the way, you need to draw both enantiomers and label the mixture as "racemic". All of the carbon atoms of the products must come from the starting material! ? H H

Q5: Draw every stereoisomer for 1-bromo-2-chloro-1,2-difluorocyclopentane. Clearly show stereochemistry by drawing the wedge-and-dashed bonds. Describe the relationship between each pair of the stereoisomers you have drawn.

Answer 2

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

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

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

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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