Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 13PP
Interpretation Introduction

Interpretation:

The order of decreasing nucleophilicity in a protic solvent of the given compounds is to be ranked.

Concept introduction:

Nucleophilicity is a measure of the ability of any nucleophile to react with an electron-deficient species.

Nucleophiles are Lewis bases, mean electron rich, and have the ability to donate electron pairs.

The order of nucleophilicity can be decided on the basis of charge.

A negatively charged nucleophile is more reactive than its conjugate acid.

In the given nucleophiles, the negatively charged nucleophiles are more reactive than the neutral one.

The nucleophile attached with electron withdrawing group has less nucleophilicity because electron withdrawing attracts electron density toward itself.

Nucleophilicity increases down the group in the periodic table.

Protic solvents are the solvents that form hydrogen bonds. They contain a hydrogen atom, which is bonded to an electronegative atom such as oxygen or nitrogen.

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4.33  Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol  (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.
5.34 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol dovolonentanol or cyclohexanol
O PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)
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