Whether products with reasonable selectivity are obtained should be identified. Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation. The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Answer 1

Question

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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C. Draw the structure for the product formed in each of step of the following synthetic sequences. 1. C NH₂ SOCI₂ or P₂O5 or POCI3 (dehydration) 1.CH3MgBr 2.H3O+ 1. NaOH, 12 2. H3O+ + yellow precipitate

H. H ÔMe Ph;P LIAIH4 compound a compound b HO. Bombykol C16H300 The above reaction scheme presents one possible synthesis of the compound. Work out the synthesis on a separate sheet of paper, and then draw the structure of compound b. Consider E/Z stereochemistry of alkenes. Do not show stereochemistry in other cases.

A. B. C. D. E. Br Br H H OH Which of these synthetic

Answer 2

Question

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Answer 3

Question

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Answer 4

Question

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

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Answer 5

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 6

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 7

Chapter 3, Problem 30P

(a)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 8

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

Answer 9

(b)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction: Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of orbital capable of donation of electrons more is the stabilization.

Answer 10

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 11

(c)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 12

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 13

(d)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 14

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 15

(e)

Interpretation Introduction

Interpretation:Whether products with reasonable selectivity are obtained should be identified.

Concept introduction:Tertiary C – H bonds reactive more readily than secondary those, in turn, are faster to react than primary. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.

The phenomenon of hyperconjugation refers to donation of σ electrons into the partly vacant p orbital lobes of radical carbon. More will be number of σ orbital capable of donation of electrons more is the stabilization.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 3.1 - Prob. 3.2TIY Ch. 3.1 - Prob. 3.3E Ch. 3.4 - Prob. 3.5TIY Ch. 3.5 - Prob. 3.6E Ch. 3.7 - Prob. 3.7E Ch. 3.7 - Prob. 3.9TIY Ch. 3.9 - Prob. 3.11TIY Ch. 3.11 - Prob. 3.12E Ch. 3 - Prob. 15P Ch. 3 - Prob. 16P

Solution Summary: The author explains that tertiary C – H bonds are reactive more readily than secondary and are faster to react than primary.

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Chapter 3 Solutions