a) Interpretation: How to synthesize butanal from 1-pentyne is to be shown. Concept introduction: Alkynes can be converted in to the corresponding alkenes by treating with H 2 in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms. To show: How to synthesize butanal from 1-pentyne.

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Answer 1

Question

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

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Each of the following syntheses requires more than one step. How would you carry them out? Show the step-wise reactions

How would the following conversion be achieved? Please show the reaction mechanism step by step

Br Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:

Answer 2

Question

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Expert Solution & Answer

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See solution

Answer 3

Question

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Answer 6

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Answer 7

Chapter 9.SE, Problem 38AP

Interpretation Introduction

a)

Interpretation:

How to synthesize butanal from 1-pentyne is to be shown.

Concept introduction:

Alkynes can be converted in to the corresponding alkenes by treating with H₂ in the presence of Lindlar catalyst. The alkene produced upon ozonolysis followed by treatment with Zn and acetic acid yields an aldehyde with lesser number of carbon atoms.

To show:

How to synthesize butanal from 1-pentyne.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne is to be shown.

Concept introduction:

Higher alkynes can be prepared first by converting the lower alkyne in to an alkynide by reacting with NaNH₂ in liquid NH₃ followed by the reaction of the alkynide with alkyl halide containing the required number of carbon atoms. The higher alkyne thus obtained upon treatment with Li in liquid NH₃ will get reduced to yield a trans alkene as the product.

To show:

How to synthesize trans- 6-methyl-3 heptene from 4-methyl-1-pentyne.

Answer 10

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Answer 11

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Answer 12

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Answer 13

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

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Chapter 9 Solutions