EP ORGANIC CHEMISTRY-OWL V2 ACCESS
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
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Chapter 24, Problem 24.36P

(a)

Interpretation Introduction

Interpretation:

Mechanism for the 1st step of the reaction has to be given along with the reason for the direction.

Concept Introduction:

Acid-base reaction:

The species that release proton or accept lone pair of electrons are called acids and the species that accept proton or donate lone pair of electrons are called base.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the oxidation step has to be shown.

Concept introduction:

The palladium reagent used as electron transfer reagent to the phenolic oxygen.

(c)

Interpretation Introduction

Interpretation:

The mechanism of the respective step has to be given along with the stereochemistry.

Concept introduction:

Diels Alder reaction:

The Diels-Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene which is called dienophile to form a substituted cyclohexene derivative.  It is one type of pericyclic reaction with a concerted mechanism and more specifically it is thermally allowed [4+2] cycloaddition.  Dienes attached to some electron donating group are good HOMO and dienophile with electron withdrawing group are good LUMO.  The mechanism is as follows,

EP ORGANIC CHEMISTRY-OWL V2 ACCESS     , Chapter 24, Problem 24.36P

(d)

Interpretation Introduction

Interpretation:

Whether the product is racemic or single enantiomer that has to be determined.

Concept introduction:

Racemic mixture:

Racemic mixture is the mixture that has equal amounts of left and right handed enantiomers of the chiral molecule.

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The poison gelsemoxonine can be isolated from the leaves of a plant native to southeastern Asia (Gelsemium elegans). A key step in a synthesis of this natural product involves a thermally initiated (70°C) sigmatropic rearrangement of the compound shown below (R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634–17637).     Draw the curved arrows for the mechanism of the formation of gelsemoxonine. Include lone pairs in your answer.
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