9701 MCQ Solution 26

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Question 26: [Organic > Hydrocarbons]:
Oxidation of an alkene Y gives a diol; further oxidation gives a diketone.

What could be Y?
A CH3CH=C(CH3)2
B (CH3)2CHCH=CH2
C C6H5CH=CHC6H5
D (C6H5)2C=CHCH3
Reference: Past Exam Paper – November 2002 Paper 1 Q26



Solution 26:
Answer: C.

To form a diol the alkene would require that the unsaturated carbons each have at least 1 hydrogen atom bonded to it. 
Option A and D do not provide this hence are eliminated. 
In option B the compound has 2 hydrogen atoms bonded to 1 of the unsaturated carbons this will cause it to become partially a primary alcohol and further oxidation will lead to fusion of a ketone from one side and a carboxylic acid on the other not a diketone. Hence option B is also incorrect. 
Option C provides a secondary alcohol on both sides hence will produce a diketone, making it the correct option.

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