OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
Question
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Chapter 9.SE, Problem 20MP
Interpretation Introduction

a)

OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th, 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)

OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th, 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)

OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th, 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.

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Chapter 9 Solutions

OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th

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
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