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Question:

A compound A with molecular formula C10H13Cl gives a white precipitation on adding silver nitrate solution. A on reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis gives C and D. C gives Cannizaro reaction but not aldol condensation. D gives aldol condensation but not Cannizaro reaction. A is:

C6H5−CH2−CH2−CH2−CH2−Cl

C6H5−CH2−CH2−C∣ClH−CH3

Solution:

The correct option is C
Compound A is an alkyl chloride. On treatment with silver nitrate, it gives the white ppt of AgCl. This confirms the presence of Cl. (tertiary carbocation stable)
Option C is correct.