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 FRP, Problem 4P

Describe how solubility could be used to distinguish between members of each of the following pairs of compounds:

(a) 4-Chlorophenol and 4 -chloro- l-methylbenzene

(b) 4-Methylphenol and 4-methylbenzoic acid

(c) 4-Methylphenol and 2, 4, 6-trinitrophenol

(d) Ethyl phenyl ether and 4-ethylphenol

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Use the symbol (V) to indicate a positive reaction and the symbol (X) to indicate a negative reaction and a () if a test was not performed in the shaded columns. Don't forget to write the number of your unknown underneath where it says number! IDENTIFICATION OF A CARBONYL COMPOUND (GROUP I) Unknowns Number Number methyl ketone Test Aldehyde ketone DNP Fehling's Tollen's X lodoform X Therefore, unknown number is IDENTIFICATION OF ALCOHOL (GROUP II) Unknown Primary alcohol Secondary Tertiary alcohol number: alcohol Test Lucas (in ~5 mins) (immediately) Bordwell - Wellman Therefore, unknown number is > x x >
2) Provide structures for the following compounds: a) ethyl acetate b) Pentanoic acid
What is the chemical equation when nitrating mixture is added to the following:(a) Cyclohexane  (b) Cyclohexene(c) Toluene

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