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A chloro compound with M.F C3H3Cl shows ...

A chloro compound with M.F `C_3H_3Cl` shows the following properties
(i) Decolourized bromine in `C Cl_4` ,
(ii)Absorbed hydrogen catalytically ,
(iii)Gave a precipitate with ammoniacal cuprous chloride solution.
Deduce the structure of the chloro compound.

Text Solution

Verified by Experts

(i)Since compound (A) absorbs hydrogen catalytically and decolourizes bromine in `C Cl_4`, it must be an unsaturated compound.
(ii)Since Compound (A) gives a precipitate with ammoniacal cuprous chloride, it must be a terminal alkyne.
The only terminal alkyne with molecular formula `underset"3-Chloro-1-propyne"(Cl-CH_2-C-=CH)`
Step 1.To explain the reactions involved in the question
(i)`underset"3-Chloro-1-propyne(A)"(Cl-CH_2-C-=CH)+ 2Br_2 overset(C Cl_4)to underset"1,1,2,2-Tetrabromo-3-chloropropane"(Cl-CH_2-CBr_2-CHBr_2)`
(ii)`Cl-CH_2-C-=CH+2H_2 overset"Catalyst"to underset"1-Chloropropane"(Cl-CH_2-CH_2-CH_3)`
(iii)`ClCH_2C-=CH+CuCl + NH_3 to underset"(Red ppt. )"(Cl-CH_2)-C-=C-Cu+NH_4Cl`
Thus, the compound (A) is 3-chloro-1-propyne.
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