(a) Interpretation: The mechanism and product for the given reaction is to be drawn. Concept introduction: The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

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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 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

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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.

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 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

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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 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 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

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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 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 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

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Answer 5

Chapter 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

Answer 6

Chapter 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Answer 7

Chapter 18, Problem 18.47P

Interpretation Introduction

(a)

Interpretation:

The mechanism and product for the given reaction is to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. Since water is amphoteric in nature, it can act as an acid as well as base depending on availability and the reaction condition. The reaction follows a different mechanism for an acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The mechanism and product for the given reaction are to be drawn.

Concept introduction:

The carbonyl carbon is electrophilic in nature due to the electronegativity difference. The nucleophile adds the electrophilic carbon of the carbonyl group. The α,β unsaturated aldehyde or ketone possesses two electrophilic centers – one is carbonyl carbon itself and second is the β carbon of the compound. Due to the resonance, there are two possible attacks for the nucleophile. When nucleophile adds β carbon of the carbonyl compound, it is called 1, 4-addition or conjugate addition, and it is a reversible addition to the carbonyl group as the carbonyl group is regenerated on acid or the protic workup. The reaction follows a different mechanism for acid and a base catalyst. When the reaction is catalyzed by the acid, the first step of the reaction is always protonation of the carbonyl oxygen, which increases the electrophilicity of the carbonyl carbon. For a base-catalyzed reaction, the first step is the deprotonation of the nucleophilic species to enhance the nucleophilic character. The conjugate base of the weak acid is a strong nucleophile. Under the basic condition, a weak acid is deprotonated easily.

Answer 10

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Answer 13

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

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