Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 7, Problem 7.30P

(a)

Interpretation Introduction

Interpretation:

The reaction sequences that are followed in the formation of the product with the given reactants has to be written.

(b)

Interpretation Introduction

Interpretation:

The reaction sequences that are followed in the formation of the product with the given reactants has to be written.

Concept Introduction:

The reagent Na / NH3 is used for the conversion of Alkynes to trans alkenes.  The reaction mechanism is the sodium forms the radical-anion in the Alkyne and then, a proton is transferred from the ammonia to the radical-anion.  The second atom in the sodium is transferred to form the carbanion.  The carbanion is neutralized by the proton of the ammonia.

(c)

Interpretation Introduction

Interpretation:

The reaction sequences that are followed in the formation of the product with the given reactants has to be written.

(d)

Interpretation Introduction

Interpretation:

The reaction sequences that are followed in the formation of the product with the given reactants has to be written.

(e)

Interpretation Introduction

Interpretation:

The reaction sequences that are followed in the formation of the product with the given reactants has to be written.

Concept Introduction:

The reagent (sia)2BH is known as Disimylborane.  It is used for chemo and regioselective hydroboration reactions.  This reagent is more selective for terminal hydroboration.

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Draw the structures of two alkenes that would react to form the haloalkane below upon addition of HBr. Your alkenes should be different regioisomers that yield the haloalkane as the major product without requiring rearrangement to occur.
Suppose the alkene in the drawing area below is put in strong acid solution, for example a solution of HBr. Highlight each carbon that might become protonated to form a carbocation intermediate. (The carbocation intermediate might then react with something else to form a final product.) سعد
Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*

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