The mechanism for the given reaction in which deprotonation at methyl substituted carbon atom occurs is to be proposed and the validation of the fact that generally this regiochemistry is not observed is to be explained. Concept introduction: Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β − hydroxy ketone or aldehyde . The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

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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 22.9, Problem 22.27P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction in which deprotonation at methyl substituted carbon atom occurs is to be proposed and the validation of the fact that generally this regiochemistry is not observed is to be explained.

Concept introduction:

Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.

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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 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 22.9, Problem 22.27P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction in which deprotonation at methyl substituted carbon atom occurs is to be proposed and the validation of the fact that generally this regiochemistry is not observed is to be explained.

Concept introduction:

Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

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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 22.9, Problem 22.27P

Interpretation Introduction

Interpretation:

The mechanism for the given reaction in which deprotonation at methyl substituted carbon atom occurs is to be proposed and the validation of the fact that generally this regiochemistry is not observed is to be explained.

Concept introduction:

Aldol condensation is defined as a condensation reaction that involves the nucleophilic addition of an enolate ion to another carbonyl group to form a β− hydroxy ketone or aldehyde. The final product is commonly known as aldol because it contains both an aldehyde group and the hydroxy group of an alcohol.

Expert Solution & Answer

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Check out a sample textbook solution

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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 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 22.9, Problem 22.27P

Interpretation Introduction