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

You are a Quality Manager for a very well-known food ingredient company that produces umami powder, and you are responsible for setting specification limits. The net weight (in grams) of bags of unami powder is monitored by taking samples of six bags on an hourly basis during production. The label on every bag reports a contents of 1KG umami powder. The process mean is μ = 1012 g, and when the process is properly adjusted, it varies with σ = 11 g. QUESTION: Your organisation strives to ensure that >99.97% of bags of umami powder produced conforms to specification. What performance process index value is required to achieve this process yield? Calculate PPK using the following formula: Ppk = (USL – mean)/3 σ Ppk = (mean -LSL)/ 3 σ

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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You are a Quality Manager for a very well-known food ingredient company that produces umami powder, and you are responsible for setting specification limits. The net weight (in grams) of bags of unami powder is monitored by taking samples of six bags on an hourly basis during production. The label on every bag reports a contents of 1KG umami powder. The process mean is μ = 1012 g, and when the process is properly adjusted, it varies with σ = 11 g. QUESTION: Your organisation strives to ensure that >99.97% of bags of umami powder produced conforms to specification. What performance process index value is required to achieve this process yield? Calculate PPK using the following formula: Ppk = (USL – mean)/3 σ Ppk = (mean -LSL)/ 3 σ

You are a Quality Manager for a very well-known food ingredient company that produces umami powder, and you are responsible for setting specification limits. The net weight (in grams) of bags of unami powder is monitored by taking samples of six bags on an hourly basis during production. The label on every bag reports a contents of 1KG umami powder. The process mean is μ = 1012 g, and when the process is properly adjusted, it varies with σ = 11 g. QUESTION: Provide a valid and full justification as to whether you would advise your manager that the process is satisfactory when it is properly adjusted, or would you seek their approval to improve the process?

You are a Quality Manager for a very well-known food ingredient company that produces umami powder, and you are responsible for setting specification limits. The net weight (in grams) of bags of unami powder is monitored by taking samples of six bags on an hourly basis during production. The label on every bag reports a contents of 1KG umami powder. The process mean is μ = 1012 g, and when the process is properly adjusted, it varies with σ = 11 g. QUESTION: Using all the available information, set the upper and lower specification limits.

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 13

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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