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Question:

An alkene "A" on reaction with O3 and Zn-H2O gives propanone and ethanal in equimolar ratio. Addition of HCl to alkene "A" gives "B" as the major product. The structure of product "B" is:

H3C−C|HCl−CH3

Cl−CH2−CH2−C|CH3H|CH3

H3C−CH2−C|HCH2Cl−CH3

H3C−CH2−C|Cl|CH3−CH3

Solution:

Correct option is C. The ozonolysis of alkene A gives propanone and ethanal in equimolar ratio. This indicates that alkene A is CH3-CH=C(CH3)2. Addition of HCl to this alkene follows Markovnikov's rule, where the hydrogen atom adds to the carbon atom with more hydrogen atoms, and the chlorine atom adds to the carbon atom with fewer hydrogen atoms. This results in the major product B as H3C-CH2-C(Cl)(CH3)2.