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 5, Problem 5.35P

(a)

Interpretation Introduction

Interpretation:

The type of isomers in limonene has to be identified.

Concept Introduction:

Chiral carbon: A carbon is said to be chiral carbon if it is bonded to four different substituents.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

(b)

Interpretation Introduction

Interpretation:

Possibility of having E, Z isomers in limonene has to be identified.

Concept Introduction:

Geometric isomers: Two compounds are considered as geometric isomers of each other if both contain same number of atoms but different in their arrangement.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the double bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the double bond.

(c)

Interpretation Introduction

Interpretation:

Reason for why isomers of limonene smell differently has to be explained.

Concept Introduction:

Chiral carbon: A carbon is said to be chiral carbon if it is bonded to four different substituents.

Chirality: It refers to a Carbon atom in a molecule that contains four different substituents.

Enantiomers: They are chiral molecules whose mirror images are not superimposable.

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2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. CH3 Ph OEt هد Ph CH3 Hint: the species on the left is an ynolate, which behaves a lot like an enolate.
b. CH3 H3C CH3 CH3 H3C an unexpected product, containing a single 9- membered ring the expected product, containing two fused rings H3C-I (H3C)2CuLi an enolate
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