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Question

A primary alcohol, C3H8O(A) on heating with sulphuric acid undergo dehydration to give an alkene, B. B, when reacted with HCl, gave C, which on treatment with aqueous KOH gives compound D(C3H8O).
A and D are:

A
functional isomers
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B
position isomers
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C
chain isomers
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D
stereoisomers.
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Solution

The correct option is C position isomers
C3H8O(A)H2SO4,ΔB(alkene)HClCaq.KOHD(C3H8O)

Since A is primary alcohol, thus it can only be CH3CH2CH2OH
upon dehydration it gives B as:

CH3CH2CH2OHH2SO4,ΔCH3CH=CH2

thus BCH3CH=CH2

Alkene with HCl will undergo addition across double bond by Markovnikov's rule as:

CH3CH=CH2+HClCH3C|ClHCH3

Thus CCH3C|ClHCH3
Alkyl halide with aq. KOH will undergo substitution reaction. Since KOH is a strong base, it will follow SN2 meachanism and will substitute Cl with OH as

CH3C|ClHCH3+aq.KOHCH3C|OHHCH3
Thus A is CH3CH2CH2OH

and D is CH3C|OHHCH3
A and D are position isomers.

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