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  4. Compound X (molecular formula, C 5 H 8 O ) does not react appreciably with Lucas reagent at room temperature but gives a precipitate with ammoniacal silver nitrate with excess of MeMgBr, 0.42 g of X gives 224 mL of CH 4 at STP. Treatment of X with H 2 in presence of Pt catalyst followed by boiling with excess HI, gives n-pentane. Suggest structure for X and write the equation involved.

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Q. Compound $X$ (molecular formula, $C _{5} H _{8} O$ ) does not react appreciably with Lucas reagent at room temperature but gives a precipitate with ammoniacal silver nitrate with excess of $MeMgBr, 0.42 \,g$ of $X$ gives $224\, mL$ of $CH _{4}$ at STP. Treatment of $X$ with $H _{2}$ in presence of $Pt$ catalyst followed by boiling with excess $HI$, gives $n$-pentane. Suggest structure for $X$ and write the equation involved.

IIT JEEIIT JEE 1992Alcohols Phenols and Ethers

Solution:

Compound $X \xrightarrow{\text{Lucas reagent}}$ No reaction at room temperature .
$C_5H_8O\xrightarrow[AgNO_3]{\text{Ammoniacal}} $ ppt, $X\xrightarrow [CH_3MgBr]{\text{Excess of }} CH_4$
$ X \xrightarrow[HI \,\text{excess}]{H_2/Pt} n-$ pentane
Above information suggest that $X$ has a terminal triple bond and it contain primary $—OH$ group.
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