1.

An organic compound (A), C_18H_20O on ozonolysis gives (B), C_10H_12O and (C) C_8H_8O_2 . Compound (B) gives iodoform reaction and products an oxime (D), C_10H_13ON on treatment with NH_2OH. Compound (D) reacts with PCI_5 in dry ether to give (E) which on hydrolysis (F), C_8H_11N and acetic gives acid. (F) on treatment with HNO_2 followed by oxidation gives phthalic acid. Compound (C) on mild oxidation gives (G) which gives effervescence with NaHCO_3 . (G) on treatment with HI produces p-hydroxy benzoic acid and CH_3I. Give structures of (A) to (G) with proper reasoning.

Answer»

Solution :
The COMPOUND (B) gives iodoform TEST as it has `-OVERSET(O)overset(||)C-CH_3` group and produces oxime with `NH_2OH`.


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