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Ozonolysis of compound ‘A’ (C7 H14) yields a mixture containing compounds ‘B’ and ‘C’. Both ‘B’ and ‘C’ give positive 2.4 - DNP test and Tollen’s test. ‘B’ undergoes Cannizzaro’s reaction. ‘C’ undergoes aldol condensation to give ‘D’. ‘B’ is also obtained by the reaction of 2, 2 –dimethylpropanol with PCC. Deduce the structures of A, B, C and D and justify your answer by giving the equations of the reactions involved.

Ozonolysis of compound ‘A’ (C7
H14) yields a mixture containing compounds ‘B’ and ‘C’.
Both ‘B’ and ‘C’ give positive 2.4 - DNP test and Tollen’s test. ‘B’ undergoes Cannizzaro’s
reaction. ‘C’ undergoes aldol condensation to give ‘D’. ‘B’ is also obtained by the reaction
of 2, 2 –dimethylpropanol with PCC. Deduce the structures of A, B, C and D and justify
your answer by giving the equations of the reactions involved.

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