question_answer

A compound A with molecular formula \[{{C}_{10}}{{H}_{13}}Cl\] gives a white precipitate 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:

A) \[{{C}_{6}}{{H}_{5}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-Cl\]

B) \[{{C}_{6}}{{H}_{5}}-C{{H}_{2}}-C{{H}_{2}}-\underset{Cl}{\mathop{\underset{|}{\mathop{C}}\,}}\,H-C{{H}_{3}}\]

C)

D)

Correct Answer: C

Solution :

[c] Compound A reacts with alc. KOH to give compound B which on further ozonolysis gives C (does not contains \[\alpha \]-H atom) and D (contains \[\alpha \]-H atom).This reaction sequence can be achieved by compounds in option [a] and [c]. Since compound A gives white ppt. with \[AgN{{O}_{3}}\] preferable option will be [c] as tert alkyi reacts with \[AgN{{O}_{3}}\] more quickly