As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism. Concept introduction: In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia ( -78 °C ), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R - species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

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Answer 1

Question

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

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Answer 2

Question

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

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Answer 3

Question

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

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Answer 4

Question

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

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Answer 5

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

Answer 6

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

Answer 7

Chapter 25, Problem 25.59P

Interpretation Introduction

Interpretation:

As we saw in this chapter, dissolving metal reductions reduce alkynes to trans alkenes. Why dissolving metal reductions fail with a terminal alkyne is to be explained. Hint: What species appear in the mechanism.

Concept introduction:

In a dissolving metal reduction, solvated electrons behave like the free radical species. When alkyne is treated with sodium metal dissolved in liquid ammonia (-78 °C), the triple bond is reduced to a double bond. But fail with a terminal alkyne. The reason is that a very strong basic R- species appears in the mechanism, which will irreversibly deprotonate a terminal alkyne. Reduction of such a deprotonated terminal alkyne would not be reasonable because it would proceed through an intermediate with adjacent negatively charged C atoms.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 25 - Prob. 25.1P Ch. 25 - Prob. 25.2P Ch. 25 - Prob. 25.3P Ch. 25 - Prob. 25.4P Ch. 25 - Prob. 25.5P Ch. 25 - Prob. 25.6P Ch. 25 - Prob. 25.7P Ch. 25 - Prob. 25.8P Ch. 25 - Prob. 25.9P Ch. 25 - Prob. 25.10P

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Chapter 25 Solutions