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

My question is whether HI adds to both double bonds, and if it doesn't, why not?

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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My question is whether HI adds to both double bonds, and if it doesn't, why not?

Strain Energy for Alkanes Interaction / Compound kJ/mol kcal/mol H: H eclipsing 4.0 1.0 H: CH3 eclipsing 5.8 1.4 CH3 CH3 eclipsing 11.0 2.6 gauche butane 3.8 0.9 cyclopropane 115 27.5 cyclobutane 110 26.3 cyclopentane 26.0 6.2 cycloheptane 26.2 6.3 cyclooctane 40.5 9.7 (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) H. H Previous Next

A certain half-reaction has a standard reduction potential Ered +1.26 V. An engineer proposes using this half-reaction at the anode of a galvanic cell that must provide at least 1.10 V of electrical power. The cell will operate under standard conditions. Note for advanced students: assume the engineer requires this half-reaction to happen at the anode of the cell. Is there a minimum standard reduction potential that the half-reaction used at the cathode of this cell can have? If so, check the "yes" box and calculate the minimum. Round your answer to 2 decimal places. If there is no lower limit, check the "no" box.. Is there a maximum standard reduction potential that the half-reaction used at the cathode of this cell can have? If so, check the "yes" box and calculate the maximum. Round your answer to 2 decimal places. If there is no upper limit, check the "no" box. yes, there is a minimum. 1 red Πν no minimum Oyes, there is a maximum. 0 E red Dv By using the information in the ALEKS…

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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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