Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
Question
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Chapter 21, Problem 21.56P

(a)

Interpretation Introduction

Interpretation:

The reagent has to be proposed for the conversion of A to B.

Concept introduction:

Michael reaction:

The nucleophile is reaction with α,β-unsaturated carbonyl compound (1,4 –addtion) which yield the addition product is called Michael reaction.

Organic Chemistry, Chapter 21, Problem 21.56P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The reagent has to be proposed for the conversion of B to C.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like LAH or NaBH4 which provides alcohol.

(c)

Interpretation Introduction

Interpretation:

The reagent has to be proposed for the conversion of C to D.

Concept introduction:

Chlorination: Alcohols reaction with thionyl chloride gives chlorinated compound.

Organic Chemistry, Chapter 21, Problem 21.56P , additional homework tip  2

(d)

Interpretation Introduction

Interpretation:

The mechanism has to be proposed for the conversion of E to F and the formation of methyl chloride has to be shown through mechanism.

(e)

Interpretation Introduction

Interpretation:

The reagent has to be proposed for the conversion of F to Fluoxetine.

Concept introduction:

Hydrolysis: Amide undergoes hydrolysis using base like sodium hydroxide gives acid.

(f)

Interpretation Introduction

Interpretation:

The possible stereoisomer’s has to be shown if the product is chiral.

Concept introduction:

Chiral:

A molecule is non superimposable on its mirror image is called chiral molecule.

Four different atoms attached to a carbon atom is called chiral molecule.

Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.

Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.

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Chapter 21 Solutions

Organic Chemistry

Ch. 21 - Name the following compounds and ions.Ch. 21 - Prob. 21.9PCh. 21 - Draw a structural formula for each compound. (a)...Ch. 21 - Molecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic...Ch. 21 - Following each name is the number of Kekul...Ch. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Which of the molecules and ions given in Problem...Ch. 21 - Prob. 21.17PCh. 21 - Naphthalene and azulene are constitutional isomers...Ch. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Following are IR and 1H-NMR spectra of compound D....Ch. 21 - Compound E (C8H10O2) is a neutral solid. Its mass...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Following are 1H-NMR and 13C-NMR spectral data for...Ch. 21 - Compound H (C8H6O3) gives a precipitate when...Ch. 21 - Compound I (C11H14O2) is insoluble in water,...Ch. 21 - Propose a structural formula for compound J...Ch. 21 - Propose a structural formula for the analgesic...Ch. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Given here are 1H-NMR and 13C-NMR spectral data...Ch. 21 - Prob. 21.32PCh. 21 - Prob. 21.33PCh. 21 - Prob. 21.34PCh. 21 - Arrange the molecules and ions in each set in...Ch. 21 - Prob. 21.36PCh. 21 - Prob. 21.37PCh. 21 - From each pair, select the stronger base.Ch. 21 - Prob. 21.39PCh. 21 - Prob. 21.40PCh. 21 - Prob. 21.41PCh. 21 - Prob. 21.42PCh. 21 - Following is an equation for iodination of...Ch. 21 - Prob. 21.44PCh. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - When warmed in dilute sulfuric acid,...Ch. 21 - In the chemical synthesis of DNA and RNA, hydroxyl...Ch. 21 - Prob. 21.49PCh. 21 - Write the products of the following sequences of...Ch. 21 - Prob. 21.51PCh. 21 - Show how to convert 1-phenylpropane into the...Ch. 21 - Prob. 21.53PCh. 21 - Cromolyn sodium, developed in the 1960s, has been...Ch. 21 - Prob. 21.55PCh. 21 - Prob. 21.56PCh. 21 - Prob. 21.57PCh. 21 - Prob. 21.58PCh. 21 - Prob. 21.59PCh. 21 - Prob. 21.60PCh. 21 - Prob. 21.61PCh. 21 - Prob. 21.62PCh. 21 - Prob. 21.63PCh. 21 - Following is a synthesis for toremifene, a...
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