a) Interpretation: How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown. Concept introduction: Terminal alkynes can be converted into their acetylides by treating with NaNH 3 in liquid NH 3 . The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. To state: How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Question

My question is whether HI adds to both double bonds, and if it doesn't, why not?

Answer 1

Question

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

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My question is whether HI adds to both double bonds, and if it doesn't, why not?

Strain Energy for Alkanes Interaction / Compound kJ/mol kcal/mol H: H eclipsing 4.0 1.0 H: CH3 eclipsing 5.8 1.4 CH3 CH3 eclipsing 11.0 2.6 gauche butane 3.8 0.9 cyclopropane 115 27.5 cyclobutane 110 26.3 cyclopentane 26.0 6.2 cycloheptane 26.2 6.3 cyclooctane 40.5 9.7 (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) H. H Previous Next

A certain half-reaction has a standard reduction potential Ered +1.26 V. An engineer proposes using this half-reaction at the anode of a galvanic cell that must provide at least 1.10 V of electrical power. The cell will operate under standard conditions. Note for advanced students: assume the engineer requires this half-reaction to happen at the anode of the cell. Is there a minimum standard reduction potential that the half-reaction used at the cathode of this cell can have? If so, check the "yes" box and calculate the minimum. Round your answer to 2 decimal places. If there is no lower limit, check the "no" box.. Is there a maximum standard reduction potential that the half-reaction used at the cathode of this cell can have? If so, check the "yes" box and calculate the maximum. Round your answer to 2 decimal places. If there is no upper limit, check the "no" box. yes, there is a minimum. 1 red Πν no minimum Oyes, there is a maximum. 0 E red Dv By using the information in the ALEKS…

Answer 2

Question

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

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Answer 3

Question

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

Expert Solution & Answer

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Answer 4

Question

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

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Answer 5

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 6

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 7

Chapter 9.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their acetylides by treating with NaNH₃ in liquid NH₃. The acetylides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed.

To state:

How to synthesize 1-pentyne from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. Acetylene has two acidic hydrogens. Both hydrogens can be replaced by alkyl groups through this process.

To state:

How to synthesize 3-hexyne from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 10

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 11

Interpretation Introduction

c)

Interpretation:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne can be reduced to the corresponding alkene by reduction with H₃ in the presence of Lindlar catalyst or by using Li in liquid ammonia.

To state:

How to synthesize 4-methyl-1-pentene from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 12

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 13

Interpretation Introduction

d)

Interpretation:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkyne needed. The alkyne undergoes hydration when treated with dilute H₃SO₄ in the presence of HgSO₄ to yield an enol which tautomerizes to a ketone.

To state:

How to synthesize 4-octanone from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 14

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 15

Interpretation Introduction

e)

Interpretation:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons is to be shown.

Concept introduction:

Terminal alkynes can be converted into their alkynides by treating with NaNH₃ in liquid NH₃. The alkynides when treated with alkyl halides with the required number of carbons yield the higher alkynes needed. The alkynes yield enols with OH on terminal carbon in hydroboration-oxidation reaction which tautomerize to yield aldehydes.

To state:

How to synthesize hexanal from acetylene using any alkyl halide with four or fewer number of carbons.

Answer 16

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Answer 17

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Answer 18

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Answer 19

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Answer 20

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Answer 21

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Answer 22

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Answer 23

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Answer 27

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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