a) Interpretation: How to convert 1-butyne in to butanone is to be shown. Concept introduction: Terminal alkynes when hydrated with dilute H 2 SO 4 in the presence of HgSO 4 are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product. To show: How to convert 1-butyne in to butanone.

Question

Where are the chiral centers in this molecule? Also is this compound meso yes or no?

Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

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Where are the chiral centers in this molecule? Also is this compound meso yes or no?

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Expert Solution & Answer

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Expert Solution & Answer

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Expert Solution & Answer

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Answer 5

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Answer 6

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Answer 7

Chapter 9.SE, Problem 37AP

Interpretation Introduction

a)

Interpretation:

How to convert 1-butyne in to butanone is to be shown.

Concept introduction:

Terminal alkynes when hydrated with dilute H₂SO₄ in the presence of HgSO₄ are converted in to enols. The addition of water takes place following Markovnikov regiochemistry. The enols upon tautomerization yield ketones as the product.

To show:

How to convert 1-butyne in to butanone.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to convert 1-butyne in to butanal is to be shown.

Concept introduction:

Terminal alkynes when hydrated using hydroboration-oxidation reaction yield an enol with OH group attached to the terminal carbon as the reaction follows anti-Markovnikov regiochemistry. The enol obtained then tautomerizes to an aldehyde.

To show:

How to convert 1-butyne in to butanal is to be shown.

Answer 10

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Answer 11

Interpretation Introduction

c)

Interpretation:

How to convert ethynylbenzene in to propynylbenzene is to be shown.

Concept introduction:

Terminal alkynes are converted in to acetylides by treating with NaNH₂ in liquid ammonia. The acetylides can be converted to higher alkynes by treating with alkyl halides having required number of carbon atoms.

To show:

How to convert ethynylbenzene in to propynylbenzene.

Answer 12

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Answer 13

Interpretation Introduction

d)

Interpretation:

How to convert propynylbenzene in to cis-1-propenylbenzene 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 hydrogenation occurs with syn stereochemistry giving a cis alkene as the product.

To show:

How to convert 1-propynylbenzene in to 1-propenylbenzene.

Answer 14

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Answer 15

Interpretation Introduction

e)

Interpretation:

How to convert 1-butyne in to propanoic acid is to be shown.

Concept introduction:

Alkynes gets cleaved when treated with powerful oxidizing agents like KMnO₄. Internal alkynes give carboxylic acids as products. Terminal alkynes give CO₂ also along with a carboxylic acid.

To show:

How to convert 1-butyne in to propanoic acid.

Answer 16

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Answer 17

Interpretation Introduction

f)

Interpretation:

How to convert 1-hexene in to 1-hexyne in two steps is to be shown.

Concept introduction:

Alkenes when treated with bromine yield a dibromo alkane which upon dehydrohalogenation with alc.KOH eliminates two molecules of HBr to yield an alkyne as the product.

To show:

How to convert 1-hexene in to 1-hexyne in two steps

Answer 18

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Answer 19

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Answer 23

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Answer 29

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

Chapter 9 Solutions