a) Interpretation: The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided. Concept introduction: The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product. To propose: The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Question

The Concept of Aromaticity 21.15 State the number of 2p orbital electrons in each molecule or ion. (a) (b) (e) (f) (c) (d) (h) (i) DA (k) 21.16 Which of the molecules and ions given in Problem 21.15 are aromatic according to the Hückel criteria? Which, if planar, would be antiaromatic? 21.17 Which of the following structures are considered aromatic according to the Hückel criteria? ---0-0 (a) (b) (c) (d) (e) (h) H -H .8.0- 21.18 Which of the molecules and ions from Problem 21.17 have electrons donated by a heteroatom?

Answer 1

Question

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

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The Concept of Aromaticity 21.15 State the number of 2p orbital electrons in each molecule or ion. (a) (b) (e) (f) (c) (d) (h) (i) DA (k) 21.16 Which of the molecules and ions given in Problem 21.15 are aromatic according to the Hückel criteria? Which, if planar, would be antiaromatic? 21.17 Which of the following structures are considered aromatic according to the Hückel criteria? ---0-0 (a) (b) (c) (d) (e) (h) H -H .8.0- 21.18 Which of the molecules and ions from Problem 21.17 have electrons donated by a heteroatom?

1. Show the steps necessary to make 2-methyl-4-nonene using a Wittig reaction. Start with triphenylphosphine and an alkyl halide. After that you may use any other organic or inorganic reagents. 2. Write in the product of this reaction: CH3 CH₂ (C6H5)₂CuLi H₂O+

3. Name this compound properly, including stereochemistry. H₂C H3C CH3 OH 4. Show the step(s) necessary to transform the compound on the left into the acid on the right. Bri CH2 5. Write in the product of this LiAlH4 Br H₂C OH

Answer 2

Question

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

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Answer 3

Question

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Expert Solution & Answer

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Answer 4

Question

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

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Answer 5

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 6

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 7

Chapter 9.SE, Problem 24MP

Interpretation Introduction

a)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.

Concept introduction:

The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.

To propose:

The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Answer 12

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Answer 23

Ch. 9.1 - Prob. 1P Ch. 9.1 - Prob. 2P Ch. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4P Ch. 9.4 - Prob. 5P Ch. 9.4 - Prob. 6P Ch. 9.4 - Prob. 7P Ch. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P

Solution Summary: The author proposes the product of the two step process shown and to give a complete electron-pushing mechanism for its formation.

Chapter 9 Solutions