The product of aldol condensation reaction followed by dehydration of butyraldehyde is to be predicted. 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.

Question

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.

Answer 1

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 22.8, Problem 22.24P

(a)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of butyraldehyde is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of acetophenone is to be predicted.

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.

(c)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of cyclohexanone is to be predicted.

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.

Give the product of the bimolecular elimination from each of the isomeric halogenated compounds. Reaction A Reaction B. КОВ CH₂ HotBu +B+ ко HOIBU +Br+ Templates More QQQ Select Cv Templates More Cras QQQ One of these compounds undergoes elimination 50x faster than the other. Which one and why? Reaction A because the conformation needed for elimination places the phenyl groups and to each other Reaction A because the conformation needed for elimination places the phenyl groups gauche to each other. ◇ Reaction B because the conformation needed for elimination places the phenyl groups gach to each other. Reaction B because the conformation needed for elimination places the phenyl groups anti to each other.

Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound

Answer 2

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 22.8, Problem 22.24P

(a)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of butyraldehyde is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of acetophenone is to be predicted.

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.

(c)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of cyclohexanone is to be predicted.

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 22.8, Problem 22.24P

(a)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of butyraldehyde is to be predicted.

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.

(b)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of acetophenone is to be predicted.

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.

(c)

Interpretation Introduction

Interpretation:

The product of aldol condensation reaction followed by dehydration of cyclohexanone is to be predicted.

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 sample textbook solution

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 22.8, Problem 22.24P

(a)

Interpretation Introduction