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

Arrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5) Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them. ▸ View Available Hint(s) Least acidity NH&F NaBr NaOH NH,Br NaCIO Reset Greatest acidity

Answer 1

Question

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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Arrange the solutions in order of increasing acidity. (Note that K (HF) = 6.8 x 10 and K (NH3) = 1.8 × 10-5) Rank solutions from least acidity to greatest acidity. To rank items as equivalent, overlap them. ▸ View Available Hint(s) Least acidity NH&F NaBr NaOH NH,Br NaCIO Reset Greatest acidity

1. Consider the following molecular-level diagrams of a titration. O-HA molecule -Aion °° о ° (a) о (b) (c) (d) a. Which diagram best illustrates the microscopic representation for the EQUIVALENCE POINT in a titration of a weak acid (HA) with sodium. hydroxide? (e)

Answers to the remaining 6 questions will be hand-drawn on paper and submitted as a single file upload below: Review of this week's reaction: H₂NCN (cyanamide) + CH3NHCH2COOH (sarcosine) + NaCl, NH4OH, H₂O ---> H₂NC(=NH)N(CH3)CH2COOH (creatine) Q7. Draw by hand the reaction of creatine synthesis listed above using line structures without showing the Cs and some of the Hs, but include the lone pairs of electrons wherever they apply. (4 pts) Q8. Considering the Zwitterion form of an amino acid, draw the Zwitterion form of Creatine. (2 pts) Q9. Explain with drawing why the C-N bond shown in creatine structure below can or cannot rotate. (3 pts) NH2(C=NH)-N(CH)CH2COOH This bond Q10. Draw two tautomers of creatine using line structures. (Note: this question is valid because problem Q9 is valid). (4 pts) Q11. Mechanism. After seeing and understanding the mechanism of creatine synthesis, students should be ready to understand the first half of one of the Grignard reactions presented in a past…

Answer 2

Question

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 3

Question

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

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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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