a) Interpretation: The product formed when 2-hexyne reacts with 2 equivalents of bromine. Concept introduction: In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond. To give: The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Question

Draw the structure of the product of the reaction given the IR and MS data. Spectral analysis of the product reveals: MS: M 150, M-15, M-43 CH.COCI AICI, IR: 3150-3000 cm, 2950-2850 cm and 1700 cm

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

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Draw the structure of the product of the reaction given the IR and MS data. Spectral analysis of the product reveals: MS: M 150, M-15, M-43 CH.COCI AICI, IR: 3150-3000 cm, 2950-2850 cm and 1700 cm

Part II. Identify whether the two protons in blue are homotopic, enantiopic, diasteriotopic, or heterotopic. a) HO b) Bri H HH c) d) H H H Br 0

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution & Answer

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution & Answer

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Answer 5

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Answer 6

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Answer 7

Chapter 9.SE, Problem 33AP

Interpretation Introduction

a)

Interpretation:

The product formed when 2-hexyne reacts with 2 equivalents of bromine.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the corresponding alkane or its derivatives as products. With one molar equivalent of a reagent they yield the corresponding alkene or its derivative as the products. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To give:

The product formed when 2-hexyne reacts with two molar equivalents of bromine.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with two molar equivalents of a reagent yield the derivatives of the corresponding alkane as the product. With one molar equivalent of a reagent they yield a derivative of the corresponding alkene as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with 1 equivalent of HBr.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product formed when 2-hexyne reacts with 1 equivalent of HBr is to be predicted.

Concept introduction:

In addition reactions, alkynes when treated with excess amount of a reagent yield the derivatives of the corresponding alkane as the product. The addition to unsymmetrical alkenes follows Markovnikov regiochemistry. The negative part of the reagent adds on to the more highly substituted carbon in triple bond.

To predict:

The product formed when 2-hexyne reacts with excess of HBr.

Answer 12

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Answer 13

Interpretation Introduction

d)

Interpretation:

The product formed when 2-hexyne reacts with Li in ammonia.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with anti stereochemistry to give a trans- alkene as product if Li in ammonia is used.

To predict:

The product formed when 2-hexyne reacts with Li in ammonia.

Answer 14

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Answer 15

Interpretation Introduction

e)

Interpretation:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is to be given.

Concept introduction:

When treated with H₂O, H₂SO₄ in the presence of HgSO₄ alkynes get hydrated to produce enols. The addition of water to unsymmetrical alkynes follows Markonikov regiochemistry while it cannot be applied in the case of symmetrical alkynes. The enols produced then undergo tautomerization to give a ketone as the product.

To predict:

The product formed when 2-hexyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Answer 16

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Answer 17

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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

Solution Summary: The author explains the product formed when 2-hexyne reacts with 2 molar equivalents of bromine.

Chapter 9 Solutions