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Question

An alcohol X when treated with hot conc . H2SO4 gave an alkene Y with formula C4H8 . This alkene on ozonolysis gives a single product with molecular formula C2H4O. The alcohol is _______.

A
butan-1-ol
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B
butan-2-ol
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C
2-methylpropan-1-ol
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D
2,2-dimethylbutan-1-ol
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Solution

The correct option is A butan-2-ol
Given that:
X(ROH)+hot conc H2SO4Y(C4H8,alkene)ozonolysis−−−−−C2H4O
Ozonolysis reaction can be represented as:
C=Cozonolysis−−−−−C=O+O=C
where all C=C breaks to form C=O. Since C2H4O can be CH3CH=O. Also, it is the only product formed after ozonolysis i.e two moles of CH3CH=O are formed. thus the alkene from which it form will be CH3CH=CHCH3 i.e. C4H8=Y
Dehydration reaction of an alcohol can be represented as:
CHCOHH+C=C
Therefore the possible alcohol that can give CH3CH=CHCH3 will be CH3CH(OH)CH2CH3=X
Thus overall reaction is
CH3CH(OH)CH2CH3+hot conc H2SO4CH3CH=CHCH3ozonolysis−−−−−CH3CH=O+O=CHCH3
The alcohol is 2-butanol.

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