A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained. Concept Introduction: A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

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Answer 1

Question

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

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Lab Data The distance entered is out of the expected range. Check your calculations and conversion factors. Verify your distance. Will the gas cloud be closer to the cotton ball with HCI or NH3? Did you report your data to the correct number of significant figures? - X Experimental Set-up HCI-NH3 NH3-HCI Longer Tube Time elapsed (min) 5 (exact) 5 (exact) Distance between cotton balls (cm) 24.30 24.40 Distance to cloud (cm) 9.70 14.16 Distance traveled by HCI (cm) 9.70 9.80 Distance traveled by NH3 (cm) 14.60 14.50 Diffusion rate of HCI (cm/hr) 116 118 Diffusion rate of NH3 (cm/hr) 175.2 175.2 How to measure distance and calculate rate

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Answer 2

Question

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

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Answer 3

Question

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

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Answer 4

Question

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

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Answer 5

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

Answer 6

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

Answer 7

Chapter 22, Problem 1Q

Interpretation Introduction

Interpretation:

A mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid needs to be explained.

Concept Introduction:

A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.

Answer 8

Expert Solution & Answer

Explanation of Solution

Below is the mechanism for the dehydration of 4-methyl cyclohexanol catalyzed by phosphoric acid:

In the first step, lone pair of electrons attack on the H atom which results in the formation positive charge on the O of the -OH group of 4-methyl cyclohexanol.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 1

Here, the good leaving group is H₂O. The derivative of hydronium ion removes a water molecule to form a carbocation intermediate.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 2

The nucleophile (H₂PO₄^-) abstracts a proton from adjacent carbon of carbocation to form 4-methyl-1-cyclohexene.

A Small Scale Approach to Organic Laboratory Techniques, Chapter 22, Problem 1Q , additional homework tip 3

Answer 9

Expert Solution & Answer

Answer 10

Expert Solution & Answer

Answer 11

Ch. 22 - Prob. 1Q Ch. 22 - Prob. 2Q Ch. 22 - Prob. 3Q Ch. 22 - Prob. 4Q Ch. 22 - Prob. 5Q

Explanation of Solution

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Chapter 22 Solutions