From the following list of possibilities and observations identify the compounds

Question

From the following list of possibilities and observations identify the compounds A thru E. The possibilities are cyclopentene, CH3CH2CH2CH2CHO, (CH3)2CH-O-CH(CH3)2, tert-amylbromide, 2-butanol, CH3CH2CH2- C - CH2CH2CH3 and p-tert-butyl phenol. The observations are:
A- water insoluble, gives brown ppt with alcoholic KMnO4, forms a dark color upon addition to a solution of FeCl3.
B- water soluble, no ppt with 2,4-DNP, yellow ppt with I2/KI/ NaOH mixture.
C- Border line water solubility, gives a brown ppt with alcoholic KMnO4, yellow ppt with 2,4-DNP, no ppt with I2/KI/NaOH mixture.
D- water insoluble, burns clean, forms white ppt with alcoholic AgNO3.
E- water insoluble, no ppt with KMnO4, yellow ppt with 2,4-DNP, no ppt with I2/KI/NaOH mixture.

Explanation / Answer

A----------p-tert-butyl phenol

B---------- (CH3)2CH-O-CH(CH3)2

C----------- CH3CH2CH2CH2CHO

D---------- tert. amyl bromide

E------------CH3CH2CH2- C - CH2CH2CH3 (assuming that middle C is C=O)

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