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 14, Problem 13PP

Practice Problem 14.13

(a) The −-Sh group is sometimes called the mercapto group. 6-Mercaptopurine is used in the treatment of acute leukemia. Write its structure.

(b) Allopurinol, a compound used to treat gout, is 6-hydroxypurine. Write its structure.

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Explain the following observations :(i) The boiling point of ethanol is higher than that of methoxymethane.(ii) Phenol is more acidic than ethanol.(iii) o- and p-nitrophenols are more acidic than phenol.
Explain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.
(c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.

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