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

Use the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 31 0.5 30 26 29 22 28 100 27 33 26 23 15 4 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. 妊 n ? Previous Next

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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Use the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 31 0.5 30 26 29 22 28 100 27 33 26 23 15 4 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. 妊 n ? Previous Next

for this question. Write the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 98.1106. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)

PLEASE READ!!! I DONT WANT EXAMPLES, I DONT WANT WORDS OR PARAGRAPHS!!! PLEASE I UNDERSTAND THE BASICS BUT THIS IS AN EXCEPTION THAT EVEN THE INTERNET CANT HELP!!!! THIS IS THE THIRD TIME I'VE SENT THOSE QUESTIONS SO PLEASE DONT RESEND THE SAME STUFF, ITS NOT HELPING ME!!! I ALSO ALREADY TRIED TO DRAW THE MECHANISM MYSELF, SO IF ITS RIGHT PLEASE TELL ME OR TELL ME WHAT I HAVE TO CHANGE!!! First image: I have to SHOW (DRAWING) the mechanism (with arows and structures of molecules) NOT WORDS PLEASE! of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary Second image: I have to show the mechanism (IMAGE) (with arrows and structures of the molecules) NOT WORDS PLEASE !! for the reaction on the left, where the alcohol A is added fast in one portion HOMEWORK, NOT EXAM!! ALL DETAILS ARE IN THE IMAGES PLEASE LOOK AT THE IMAGES, DONT LOOK AT THE AI GENERATED TEXT!!!

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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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