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

A solution contains 0.097 M Ce3+, 1.55x10-3 M Ce4+, 1.55x10-3 M Mn2+, 0.097 M MnO4-, and 1.00 M HClO4 (F= 9.649 x 104 C/mol). a) Write a balanced net reaction that can occur between species in this solution. b) Calculate deltaG0 and K for the reaction. c) Calculate E and deltaG for the conditions given. Ce4+ + e- = Ce3+ E0= 1.70 V MnO4- + 8H+ + 5e- = Mn2+ + 4H2O E0= 1.507 V

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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A solution contains 0.097 M Ce3+, 1.55x10-3 M Ce4+, 1.55x10-3 M Mn2+, 0.097 M MnO4-, and 1.00 M HClO4 (F= 9.649 x 104 C/mol). a) Write a balanced net reaction that can occur between species in this solution. b) Calculate deltaG0 and K for the reaction. c) Calculate E and deltaG for the conditions given. Ce4+ + e- = Ce3+ E0= 1.70 V MnO4- + 8H+ + 5e- = Mn2+ + 4H2O E0= 1.507 V

1. Provide a step-by-step mechanism for formation of ALL STEREOISOMERS in the following reaction. Na HCO3 (Sodium bicarbonate, baking soda) is not soluble in CH2Cl2. The powder is a weak base used to neutralize strong acid (pKa < 0) produced by the reaction. Redraw the product to show the configuration(s) that form at C-2 and C-4. Br2 OH CH2Cl2 Na* HCO3 Br HO OH + Na Br +

2. Specify the solvent and reagent(s) required to carry out each of the following FGI. If two reagent sets must be used for the FGI, specify the solvent and reagent(s) for each reagent set. If a reaction cannot be carried out with reagents (sets) class, write NP (not possible) in the solvent box for reagent set #1. Use the letter abbreviation for each solvent; use a number abbreviation for reagent(s). Solvents: CH2Cl2 (A); H₂O (B); Reagents: HBr (1); R₂BH (6); H2SO4 (2); CH3OH (C); Br₂ (3); CH3CO₂H (D) NaHCO3 (4); Hg(OAc)2 (5); H₂O2/HO (7); NaBH4 (8) Reagent Set #1 Reagent Set #2 FGI + enant OH Solvent Reagent(s) Solvent Reagent(s)

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.

Expert Solution & Answer

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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