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Given that anisole (methoxybenzene) protonates primarily on oxygen in concentrated

Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise ISBN: 9781936221349 461

Solution for problem 16.64 Chapter 16

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise

Organic Chemistry | 6th Edition

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Problem 16.64

Given that anisole (methoxybenzene) protonates primarily on oxygen in concentrated H2SO4, explain why 1,3,5- trimethoxybenzene protonates primarily on a carbon of the ring. As part of your reasoning, draw the structure of each conjugate acid.

Step-by-Step Solution:
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Relationship G, G, and Q  Reaction not at equilibrium, G = G + RTlnQ o R = gas constant (8.314 J/K x mol) o T = absolute temperature o Q = reaction quotient Ex: N 2 4g) 2NO (g) 2 2 Q= [NO ]2 [2 4 ] G reaction = nGproducts ­  nGreactants = (2 mol)(51.3 kJ/mol) – (1 mol)(97.8 kJ/mol) = 4.8 kJ Relationship G and k  Reaction at equilibrium: G = 0 and Q = k 0 = G + RTlnk or G = ­RTlnK or k = e ­ G /RT   lnk k At equilibrium Neg. pos. >1

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Chapter 16, Problem 16.64 is Solved
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Textbook: Organic Chemistry
Edition: 6
Author: Marc Loudon, Jim Parise
ISBN: 9781936221349

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Given that anisole (methoxybenzene) protonates primarily on oxygen in concentrated