EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
EBK ORGANIC CHEMISTRY STUDY GUIDE AND S
6th Edition
ISBN: 9781319385415
Author: PARISE
Publisher: VST
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Chapter 10, Problem 10.21P
Interpretation Introduction

(a)

Interpretation:

The absolute configuration of the alkyl chloride obtained from the reaction of thionyl chloride with (S)-CH3CH2CH2CHDOH is to be stated.

Concept introduction:

The nucleophilic substitution reactions are the reactions in which one nucleophile is substituted by the another nucleophile. These reactions depend upon the nucleophilicity and concentration of the incoming nucleophile.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of incoming nucleophile and removal of outgoing nucleophile takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

The absolute configuration of 2-bromopentane obtained from the reaction of Ph3PBr2 with the R enantiomer of 2-pentanol is to be stated.

Concept introduction:

The nucleophilic substitution reactions are the reactions in which one nucleophile is substituted by the another nucleophile. These reactions depend upon the nucleophilicity and concentration of the incoming nucleophile.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of incoming nucleophile and removal of outgoing nucleophile takes place simultaneously.

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(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?
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Chapter 10 Solutions

EBK ORGANIC CHEMISTRY STUDY GUIDE AND S

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