An organic compound C3H5Cl (A) when treated with magnesium in diy ether gives (B) which on treating with CO2 followed by acid hydrolysis gives C4H6O2 (C). (C) is also obtained on oxidation of a hydrocarbon (D) C8H12. Structure of A is

Question

An organic compound C3H5Cl (A) when treated with magnesium in diy ether gives (B) which on treating with CO2 followed by acid hydrolysis gives C4H6O2 (C). (C) is also obtained on oxidation of a hydrocarbon (D) C8H12. Structure of A is (A) CH2 = CH — CH2 — Cl (B)  (C)  (D)

Tardigrade Admin · Accepted Answer

The reaction can be summerised as, underset(A)C 3 H 5 Cl + Mg xrightarrow textether (B) xrightarrow[(ii) H2O/H+](i) CO2 underset(C)C 4 H 6 O 2 xrightarrow[ O ] underset(D)C 3 H 12 Let us consider any one of a, b and c options as C 3 H 5 Cl and proceeds the reaction CH2 = underset(A)CH-CH2-Cl xrightarrow[ textether]MgCH2-CH-CH2-MgCl

As it is known that carboxylic acid is also obtained on the oxidation of corresponding hydrocarbon. R- CH = CH -R stackrel[ O ] longrightarrow R COOH +R COOH Thus, by knowing the structure of (C) as as CH 2= CH - CH 2- COOH, we can say that structure of C 6 H 12 will be CH 2= CH - CH 2- CH = CH - CH 2-CH = CH 2 But this hydrocarbon on oxidation will not give acid (C) having molecular formula C 4 H 6 O 2 but it will give malonic acid, CO 2 and water. CH 2= CH - CH 2- CH = CH - CH 2

Thus, among a, b, c options none will give satisfactory explanation regarding the structure of hydrocarbon as they contain double bond hence, correct structure of (A) will be cyclopropyl chloride.

Q. An organic compound $C_{3} H_{5} Cl (A)$ when treated with magnesium in diy ether gives $(B)$ which on treating with $C O_{2}$ followed by acid hydrolysis gives $C_{4} H_{6} O_{2} (C)$ . $(C)$ is also obtained on oxidation of a hydrocarbon $(D) C_{8} H_{12}$ . Structure of $A$ is

$C H_{2} = C H — C H_{2} — Cl$

Q. An organic compound C3​H5​Cl(A) when treated with magnesium in diy ether gives (B) which on treating with CO2​ followed by acid hydrolysis gives C4​H6​O2​(C). (C) is also obtained on oxidation of a hydrocarbon (D)C8​H12​. Structure of A is

CH2​=CH—CH2​—Cl

Q. An organic compound $C_{3} H_{5} Cl (A)$ when treated with magnesium in diy ether gives $(B)$ which on treating with $C O_{2}$ followed by acid hydrolysis gives $C_{4} H_{6} O_{2} (C)$ . $(C)$ is also obtained on oxidation of a hydrocarbon $(D) C_{8} H_{12}$ . Structure of $A$ is

$C H_{2} = C H — C H_{2} — Cl$