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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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1
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