a) Interpretation: The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH 3 is to be given. Concept introduction: Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product. The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical. To propose: The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH 3 .

Question

||| 7:47 ull 57% ← Problem 19 of 48 Submit Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the product of this carbocation rearrangement. Include all lone pairs and charges as appropriate. H 1,2-alkyl shift +

Answer 1

Question

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

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||| 7:47 ull 57% ← Problem 19 of 48 Submit Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the product of this carbocation rearrangement. Include all lone pairs and charges as appropriate. H 1,2-alkyl shift +

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Answer 2

Question

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

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Answer 3

Question

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

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Answer 4

Question

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

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Answer 5

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

Answer 6

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Answer 7

Chapter 9.SE, Problem 22MP

Interpretation Introduction

a)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 2-pentyne is reduced with Li in NH₃.

Answer 8

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Answer 9

Interpretation Introduction

b)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from deuteratedammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from the solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when 3-methyl-1-butyne is reduced with Li in ND₃.

Answer 10

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

Answer 11

Interpretation Introduction

c)

Interpretation:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃ is to be given.

Concept introduction:

Lithium metal donates an electron to the alkyne to give an anion radical which in the next step abstracts a proton from ammonia solvent to yield a vinylic radical. In the third step the vinylic radical accepts a second electron from another Li atom to produce a vinylic anion which in the fourth step abstracts another proton from ammonia solvent to yield the final trans product.

The addition takes place with trans stereochemistry. The stereochemistry is established in the third step when the less hindered vinylic anion is formed from vinylic radical.

To propose:

The product formed and the electron pushing mechanism for its formation, when propynylbenzene is reduced with Li in NH₃.

Answer 12

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Answer 23

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 that 2-pentyne gets an electron from the lithium metal to give an anion radical which in the next step abstracts a proton from ammonia solvent.

Chapter 9 Solutions