Q. The dihalogen derivative ‘X’ of a hydrocarbon with three carbon atoms reacts with alcoholic $KOH$ and produces another hydrocarbon which forms a red precipitate with ammoniacal $Cu_{2}Cl_{2}.$ ‘X’ gives an aldehyde on reaction with aqueous $KOH$. The compound ‘X ’ is

A) 1,3-dichloropropane
B) 1,2-dichloropropane
C) 2,2-dichloropropane
D) 1,1-dichloropropane
Explanation

(d)
$‘X’$ is a three carbon compound with two halogen atom, so its molecular formula is $C_{3}H_{6}Cl_{2}$. Only terminal alkynes give red ppt. with ammoniacal $Cu_{2}{Cl}_{2}$, so the hydrocarbon produced by the reaction of $‘X’$ with alc. $KOH$, must be a terminal alkyne $(i.e.,\ CH_{3}C \equiv CH)$.
$C_{3}H_{6}Cl_{2}\overset{Alc.KOH}{\rightarrow}CH_{3}C \equiv CH\overset{Amm.Cu_{2}Cl_{2}}{\rightarrow}CH_{3}C \equiv CCu \downarrow$
red ppt.
Compound $(X)$ gives an aldehyde when reacts with aqueous $KOH$. This suggests that both the halogens are present on same terminal carbon atom. Thus, the formula of compound $(X)$ is
[image:13_image267.emf]and the reactions are as follows
[image:13_image268.emf]
$CH_{3}C \equiv CH\underset{Cu_{2}Cl_{2}}{\overset{Ammoniacal}{\rightarrow}}CH_{3}C \equiv CCu \downarrow$
red ppt.
[image:13_image269.emf]
[image:13_image270.emf]

Dr. Abubacker
Reviewed by Dr. Abubacker

Physics Educator & NEET/JEE Specialist

Ph.D. in Physics with 19+ years of teaching experience.

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