To explain the following result obtain from theHammett equation. Concept introduction: Hammett reaction constant ( ρ )is the slope of logarithm of rate constant ( logk ) versusHammett substitution constant ( σ ) graph. The logk Vs σ graph can be represented as: The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Question

The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below: The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities. a. Cl: ortho > meta > para b. NO2: ortho > para > meta c. NH2: meta > para > ortho

Answer 1

Question

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

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The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below: The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities. a. Cl: ortho > meta > para b. NO2: ortho > para > meta c. NH2: meta > para > ortho

Explain why a carbonyl absorption shifts to lower frequency in an α,β-unsaturated carbonyl compound—a compound having a carbonyl group bonded directly to a carbon–carbon double bond. For example, the carbonyl absorption occurs at 1720 cm−1 for cyclohexanone, and at 1685 cm−1 for cyclohex-2-enone.

In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?

Answer 2

Question

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

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Answer 3

Question

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

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Answer 4

Question

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

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Answer 5

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 6

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 7

Chapter 15, Problem 92P

(a)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction:

Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 10

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 11

(c)

Interpretation Introduction

Interpretation:

To explain the following result obtain from theHammett equation.

Concept introduction: Hammett reaction constant (ρ)is the slope of logarithm of rate constant (logk) versusHammett substitution constant (σ) graph. The logk Vs σ graph can be represented as:

The negative value of the ρ means electrons flow out from the aromatic ring in the rate-determining step and positive value of ρ electrons flow into the aromatic ring in the rate determining step.

Answer 12

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Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3P Ch. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6P Ch. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...

Solution Summary: The author explains the Hammett reaction constant, which is the slope of logarithm of rate constant ( logk ) versusHammet

Chapter 15 Solutions