a) Interpretation: The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn. Concept introduction: In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg 2+ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate. To draw: The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Question

The following molecule can undergo keto–enol tautomerization upon addition of hydroxide. Draw the structure of the enol form and the mechanism by which it forms.

Answer 1

Question

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

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The following molecule can undergo keto–enol tautomerization upon addition of hydroxide. Draw the structure of the enol form and the mechanism by which it forms.

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Answer 2

Question

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

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Answer 3

Question

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

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Answer 4

Question

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

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Answer 5

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

Answer 6

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Answer 7

Chapter 9.SE, Problem 20MP

Interpretation Introduction

a)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of ethynylbenzene.

Answer 8

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Answer 9

Interpretation Introduction

b)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of propyne.

Answer 10

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

Answer 11

Interpretation Introduction

c)

Interpretation:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne is to be drawn.

Concept introduction:

In the first step attack of the Ï€ electrons of the triple bond on the electrophilic Hg²⁺ ion takes place to yield a mercury containing vinylic carbocation intermediate. In the second step nucleophilic attack of water takes place on the carbocation. A new C-O bond is formed leading to the formation of a protonated mercury containing enol. In the third step water abstracts a proton from the protonated enol to yield the organomercury intermediate.

To draw:

The electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of 3-methyl-1-butyne.

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 the electron pushing mechanism for the formation of the organo-mercury intermediate obtained during the mercury catalyzed hydration of phenylacetylene.

Chapter 9 Solutions