a) Interpretation: The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed. Concept introduction: The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon. To propose: The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Question

13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)! Google

Answer 1

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)! Google

Print Last Name, First Name Initial Statifically more chances to abstract one of these 6H 11. (10pts total) Consider the radical chlorination of 1,3-diethylcyclohexane depicted below. 4 4th total • 6H total 래 • 4H total 21 total ZH 2H Statistical H < 3° C-H weakest - product abstraction here bund leads to thermo favored a) (6pts) How many unique mono-chlorinated products can be formed and what are the structures for the thermodynamically and statistically favored products? Product 6 Number of Unique Mono-Chlorinated Products Thermodynamically Favored Product Statistically Favored Product b) (4pts) Draw the arrow pushing mechanism for the FIRST propagation step (p-1) for the formation of the thermodynamically favored product. Only draw the p-1 step. You do not need to include lone pairs of electrons. No enthalpy calculation necessary H H-Cl Waterfox

10. (5pts) Provide the complete arrow pushing mechanism for the chemical transformation → depicted below Use proper curved arrow notation that explicitly illustrates all bonds being broken, and all bonds formed in the transformation. Also, be sure to include all lone pairs and formal charges on all atoms involved in the flow of electrons. CH3O II HA H CH3O-H H ①

Answer 2

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 3

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 4

Question

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

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Answer 5

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 6

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 7

Chapter 7.SE, Problem 60AP

Interpretation Introduction

a)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocation is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 8

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 9

Interpretation Introduction

b)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation can rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 10

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 11

Interpretation Introduction

c)

Interpretation:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given is to be proposed.

Concept introduction:

The stability of carbocations are in the order tertiary > secondary > primary. A carbocation will rearrange to a more stable carbocation either by a hydride shift or by an alkyl shift from adjacent carbon.

To propose:

The structure of more stable carbocation obtainable by the rearrangement of the carbocation given.

Answer 12

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Answer 23

Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2P Ch. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5P Ch. 7.3 - Prob. 6P Ch. 7.3 - Prob. 7P Ch. 7.4 - Prob. 8P Ch. 7.4 - Prob. 9P Ch. 7.4 - Prob. 10P

Solution Summary: The author proposes the structure of more stable carbocation obtainable by the rearrangement of the n-butylcarbocated.

Chapter 7 Solutions