Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 10, Problem 10.12P
Interpretation Introduction

Interpretation:

The curved-arrow mechanism for the rearrangement of alcohol is to be stated.

Concept introduction:

The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. First is the elimination of leaving group to give carbocation intermediate. Second step is the addition of incoming nucleophile to the carbocation intermediate.

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(a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?
Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)
10.16 Design a preparation of each of the following compounds from an alcohol using sulfonate ester methodology. (a) (b) -CH,CH,CH,– SCH, 10.21 (a) According to the mechanism of the reaction shown in Eq. 10.34, what would be the absolute configuration of the alkyl chloride obtained from the reaction of thionyl chloride with (S)-CH,CH,CH,CHD-OH? Explain. (b) According to the mechanism shown in Eqs, 10,36a and 10.36b, what would be the absolute configuration of 2-bromopentane obtained from the reaction of Ph,PBr, with the R enantiomer of 2-pentanol? Explain.

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