An organic compound (A), C18H20O on ozonolysis givea (B), C10H12O and (C), C8H8O2. Compound (B) gives iodoform reaction and produces an oxide (D), C10H13ON on treatment with NH2OH. Compound (D) reacts with PCl5 in dry ether to give (E) which on hydrolysis gives (F), C8H11N and acetic acid. (F) on treatment with HNO2 followed by oxidation gives pthalic acid. Compound (C) on mild oxidation gives (G) which gives effervescene with NaHCO3. (G) on treatment with HI produces p-hydroxy benzoic acid and CH3I.
Give structures of (A) to (G) with proper reasoning.
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alkene A is symmetric because it gives a carboxyl compound (C8H8O) on ozonolysis.
C8H8O - NAOH+I2 C6H5COONa
On the basis of compound B structure A is symmetric alkenes show the property of geometrical isomerism.
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