Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 22.4, Problem 7P
Interpretation Introduction

Interpretation:

Considering the resonance structure, the reason that the given compounds are weaker base than aniline corresponding to the effect of the substituent is to be explained.

Concept Introduction:

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The major factors that contribute to the basic strength are s character, inductive effect and polarity.

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The high percentage of s character decreases the basicity, Positive inductive effect increases the basic strength of the compounds, whilenegative inductive effect decreases the basic strength of the compounds.

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An acidic substance in a reaction donates a proton, while a base in a reaction accepts a proton.

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The elimination of a proton leads to the formation of a conjugate base. If the base accepts a proton the species formed is known as conjugate acid.

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. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavage
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