a) Interpretation: The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst. Concept introduction: Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used. To predict: The product formed when 5-decyne reacts with H 2 in the presence of Lindlar catalyst.

Question

Want to see more full solutions like this?

Answer 1

Question

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 18

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 19

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 20

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Students have asked these similar questions

Determine whether the following reaction is an example of a nucleophilic substitution reaction: H NO2 H+ NO 2 + Molecule A Molecule B Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. What word or two-word phrase is used to describe the role Molecule A plays in this reaction? What word or two-word phrase is used to describe the role Molecule B plays in this reaction? Use a 6 + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. O Yes ○ No ☐ 0 dx 000 HE ?

Draw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. :0: NaOH H

5. Calculate the total amount of heat transferred as 50 g of wat Specific heat H₂O (g) 2.00 J/g°C -10 °C. Specific heat H₂O (1) Specific heat H₂O (s) 4.18 J/g°C 2.11 J/g°C Heat of vaporization 2260 J/g Heat of fusion 334 J/g Melting point 0°C 6. Calculate the total amount of heat transferred as 25 g of water is heated from 50 °C to 100 °C as a gas. Boiling point 100 °C

Answer 2

Question

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Answer 6

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Answer 7

Chapter 9.SE, Problem 32AP

Interpretation Introduction

a)

Interpretation:

The product formed when 5-decyne reacts with H2 in the presence of Lindlar catalyst.

Concept introduction:

Alkynes can be reduced by treatment with hydrogen in the presence of a catalyst. The hydrogenation occurs with syn stereochemistry to give a cis alkene as product if Lindler catalyst is used.

To predict:

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst.

Answer 8

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Lindlar catalyst, the addition of hydrogens to both carbons in triple bond takes place resulting in the formation of cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 3

Answer 13

Conclusion

The product expected when 5-decyne reacts with H₂ in the presence of Lindlar catalyst is cis-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 4

Answer 14

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Answer 15

Interpretation Introduction

b)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with Li in ammonia.

Answer 16

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

When 5-decyne reacts with hydrogen in the presence of Li in ammonia, the addition of hydrogens to both carbons in triple bond takes place following antistereochemistry resulting in the formation of trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 7

Answer 21

Conclusion

The product expected when 5-decyne reacts with Li in ammonia is trans-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 8

Answer 22

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Answer 23

Interpretation Introduction

c)

Interpretation:

The product formed when 5-decyne reacts with one equivalent of bromine.

Concept introduction:

Alkynes undergo addition reactions with anti stereochemistry when treated with bromine. When treated with one equivalent of bromine a trans-dibromoalkene results as product by the addition of bromine atoms to the carbons in triple bond from opposite faces.

To predict:

The product formed when 5-decyne reacts with one equivalent of bromine.

Answer 24

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-hexene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 10

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

When 5-decyne reacts with bromine, the addition of bromine to both carbons in triple bond takes place following anti stereochemistry, resulting in the formation of trans-5,6-dibromo-5-decene as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 11

Answer 29

Conclusion

The product formed when 5-decyne reacts with one equivalent of bromine is trans-5,6-dibromo-5-decene.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 12

Answer 30

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Answer 31

Interpretation Introduction

d)

Interpretation:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Concept introduction:

Alkynes get hydrated in the hydroboration oxidation reaction. The reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product.

To predict:

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-.

Answer 32

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH- is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 14

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

When 5-decyne is treated with BH₃ in THF followed by with H₂O₂, OH-, the reaction occurs with syn stereochemistry following anti Markovnikov regiochemistry to produce an enol. The enol then tautomerizes to yield a ketone as the product. The Boron and hence the OH group adds to the less highly substituted carbon in triple bond and H adds to the more highly substituted carbon atom in the triple bond to produce an enol. The enol then tautomerizes to yield the ketone as the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 15

Answer 37

Conclusion

The product formed when 5-decyne reacts with BH₃ in THF followed by with H₂O₂, OH-is 6-decanone.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 16

Answer 38

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Answer 39

Interpretation Introduction

e)

Interpretation:

The product formed when 5-decyne 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 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄.

Answer 40

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

5-Decyne is a symmetrical alkyne. Hence Markonikov regiochemistry is not applicable. When treated with dilute H₂SO₄ in the presence of HgSO₄, the OH group adds to a carbon in triple bond and H adds to the other carbon in triple bond to yield an enol. The enol then tautomerizes to yield the ketone, 5-decanone.

Answer 45

Conclusion

The product formed when 5-decyne reacts with H₂O, H₂SO₄ in the presence of HgSO₄ is 5-decanone.

Answer 46

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23

Conclusion

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 24

Answer 47

Interpretation Introduction

f)

Interpretation:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is to be given.

Concept introduction:

When treated with excess H₂, Pd/C catalyst the alkynes react with two molar equivalents of hydrogen to give the parent alkane as the product.

To predict:

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C.

Answer 48

Expert Solution

Answer to Problem 32AP

The product formed when 5-decyne reacts with excess H₂ in the presence of Pd/C is n-decane.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 22

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

When 5-Decyne is treated with excess H₂ in the presence of Pd/C, two molar equivalents of hydrogens add to the triple bond. The corresponding alkane, n-decane is the product.

EBK ORGANIC CHEMISTRY, Chapter 9.SE, Problem 32AP , additional homework tip 23