Organic Chemistry - With Access (Custom)
Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
Question
Book Icon
Chapter 9.SE, Problem 20MP
Interpretation Introduction

a)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 20MP , additional homework tip  1

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 π 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)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 20MP , additional homework tip  2

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 π 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)

Organic Chemistry - With Access (Custom), Chapter 9.SE, Problem 20MP , additional homework tip  3

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 π 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.

Blurred answer
Students have asked these similar questions
Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism of the reactions. Br MeOH OSO2CH3 MeOH
Provide the correct IUPAC name for the compound shown here. Reset cis- 5- trans- ☑ 4-6- 2- 1- 3- di iso tert- tri cyclo sec- oct but hept prop hex pent yl yne ene ane
Q6: Predict the major product(s) for the following reactions. Note the mechanism (SN1, SN2, E1 or E2) the reaction proceeds through. If no reaction takes place, indicate why. Pay attention to stereochemistry. NaCN DMF Br σ Ilm... Br H Br H H NaCN CH3OH KOtBu tBuOH NaBr H₂O LDA Et2O (CH3)2CHOH KCN DMSO NaOH H₂O, A LDA LDA System

Chapter 9 Solutions

Organic Chemistry - With Access (Custom)

Ch. 9.8 - Prob. 11PCh. 9.9 - Show the terminal alkyne and alkyl halide from...Ch. 9.9 - Beginning with acetylene and any alkyl halide...Ch. 9.SE - Name the following alkynes, and predict the...Ch. 9.SE - From what alkyne might each of the following...Ch. 9.SE - Prob. 16VCCh. 9.SE - The following cycloalkyne is too unstable to...Ch. 9.SE - Prob. 18MPCh. 9.SE - Assuming that strong acids add to alkynes in the...Ch. 9.SE - Prob. 20MPCh. 9.SE - Prob. 21MPCh. 9.SE - Prob. 22MPCh. 9.SE - Prob. 23MPCh. 9.SE - Prob. 24MPCh. 9.SE - Reaction of acetone with D3O+ yields...Ch. 9.SE - Give IUPAC names for the following compounds:Ch. 9.SE - Draw structures corresponding to the following...Ch. 9.SE - Prob. 28APCh. 9.SE - Prob. 29APCh. 9.SE - Prob. 30APCh. 9.SE - Predict the products from reaction of l-hexyne...Ch. 9.SE - Prob. 32APCh. 9.SE - Prob. 33APCh. 9.SE - Propose structures for hydrocarbons that give the...Ch. 9.SE - Identify the reagents a-c in the following scheme:Ch. 9.SE - Prob. 36APCh. 9.SE - Prob. 37APCh. 9.SE - Prob. 38APCh. 9.SE - How would you carry out the following...Ch. 9.SE - Prob. 40APCh. 9.SE - Synthesize the following compounds using 1-butyne...Ch. 9.SE - Prob. 42APCh. 9.SE - Prob. 43APCh. 9.SE - Prob. 44APCh. 9.SE - Prob. 45APCh. 9.SE - A hydrocarbon of unknown structure has the formula...Ch. 9.SE - Compound A(C9H12) absorbed 3 equivalents of H2 on...Ch. 9.SE - Hydrocarbon A has the formula C12H8. It absorbs 8...Ch. 9.SE - Occasionally, a chemist might need to invert the...Ch. 9.SE - Prob. 50APCh. 9.SE - Prob. 51APCh. 9.SE - Prob. 52APCh. 9.SE - Prob. 53APCh. 9.SE - Prob. 54APCh. 9.SE - Prob. 55APCh. 9.SE - Prob. 56APCh. 9.SE - Prob. 57AP
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning