Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 22, Problem 22.53P

(a)

Interpretation Introduction

Interpretation:

Mechanism for the conversion of compound (A) to compound (B) has to be given.

Concept Introduction:

Acid catalyzed reactions:

In an organic synthesis reactions, most of the reactions are initiated by the abstraction of proton from acids by the reactant.  Sulphuric acid is one of the reagent used for this purposes.

(b)

Interpretation Introduction

Interpretation:

For the conversion of compound (B) to compound (C) reagents has to be proposed.

Concept Introduction:

Grignard addition:

It is an addition of organomagnesium halide to an aldehyde or ketone, to form a secondary or tertiary alcohol respectively.

(c)

Interpretation Introduction

Interpretation:

Mechanism for the conversion of compound (C) to compound (D) has to be given.

Concept Introduction:

Acid catalyzed reactions:

In an organic synthesis reactions, most of the reactions are initiated by the abstraction of proton from acids by the reactant.  Sulphuric acid is one of the reagent used for this purposes.

(d)

Interpretation Introduction

Interpretation:

For the conversion of compound (d) to amitriptyline reagents has to be proposed.

Concept Introduction:

SN2 reaction:

SN2 stands for bimolecular nucleophilic substitution reaction.  In this type of reactions, simultaneous bond breaking and bond making steps are involved.

Organic Chemistry, Chapter 22, Problem 22.53P

(e)

Interpretation Introduction

Interpretation:

The chirality of amitriptyline and the number of possible stereoisomers has to be checked.

Concept Introduction:

Stereoisomers and chiral:

Isomers differing only in their spatial arrangement of atoms are called as stereoisomers.

The geometric property of a molecule that cannot be superimposed on its mirror image is known as chirality.  Chiral carbon is the one which is attached with four different groups or atoms.

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Chapter 22 Solutions

Organic Chemistry

Ch. 22 - What product do you predict from the reaction of...Ch. 22 - Other groups besides H+ can act as leaving groups...Ch. 22 - Prob. 22.14PCh. 22 - Prob. 22.15PCh. 22 - Prob. 22.16PCh. 22 - Prob. 22.17PCh. 22 - Suggest a reason why the nitroso group, N=O, is...Ch. 22 - Prob. 22.19PCh. 22 - Prob. 22.20PCh. 22 - The following molecules each contain two aromatic...Ch. 22 - Prob. 22.22PCh. 22 - Prob. 22.23PCh. 22 - The insecticide DDT is prepared by the following...Ch. 22 - Prob. 22.25PCh. 22 - Prob. 22.26PCh. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Prob. 22.32PCh. 22 - Show how to prepare each compound from...Ch. 22 - Prob. 22.34PCh. 22 - Show reagents and conditions to bring about the...Ch. 22 - Prob. 22.36PCh. 22 - Propose a synthesis for each compound from...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - The first widely used herbicide for the control of...Ch. 22 - Prob. 22.40PCh. 22 - Prob. 22.41PCh. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - Cancer of the prostate is the second leading cause...Ch. 22 - Prob. 22.45PCh. 22 - Prob. 22.46PCh. 22 - Prob. 22.47PCh. 22 - When certain aromatic compounds are treated with...Ch. 22 - Prob. 22.49PCh. 22 - Following is the structure of miconazole, the...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Show how the antidepressant venlafaxine (Effexor)...Ch. 22 - Prob. 22.57PCh. 22 - Given this retrosynthetic analysis, propose a...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - A newer generation of antipsychotics, among them...Ch. 22 - Prob. 22.63P
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