An unknown unbranched hydrocarbon with molecular formula $C_{5} H_{10}$ decolourise $B r_{2} + H_{2} O$ and onreaction with $H C l / C C l_{4}$ give 2-chloro pentane as major product. Identify total number of possible reactants. (excluding stereochemistry)

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Solution

Chlorine to be added at $2^{n d}$ position there are two possibilities double bond may present at first carbon or second carbon.
Unsaturated hydrocarbons decolurises $B r_{2} + H_{2} O$ . According to a given molecular formula, $C_{5} H_{10}$ structures may be
$H_{2} C = C H - C H_{2} - C H_{2} - C H_{3}$
1 - pentene
$C H_{3} - C H = C H - C H_{2} - C H_{3}$
2-pentene

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