HARD
JEE Advanced
IMPORTANT
Earn 100

An aromatic compound (A) with molecular formula C14H20O4 with HIO4 gives 2 moles of (B) C2H4O and
mole of (C) C10H8O2. Both (B) and (C) give yellow precipitate with I2/OH-.(C) with I2/OH- gives (D) C8H6O4
and 2 moles of CHI3. Compound (D) with red P and HI gives (E). Which has zero dipole moment? Give the structures of A, B, C, D and E.

Important Questions on Reduction and Oxidation Reactions of Organic Compounds

HARD
JEE Advanced
IMPORTANT
An optically active alcohol A C6H10O absorbs two moles of hydrogen per mole of A. Upon catalytic hydrogenation, gives a product B. The compound B is resistant to oxidation by CrO3 and does not show any optical activity. Deduce the structures of A and B.
HARD
JEE Advanced
IMPORTANT
An unknown hydrocarbon (A), with formula C6H12, react with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also react with OsO4 to give a diol (B). When oxidized with KMnO4 in acidic solution, 'A' gives two fragments. One fragment is propanoic acid and other fragment is a ketone (C). What are the structures of A, B and C ?
HARD
JEE Advanced
IMPORTANT
An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic reduction to give decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-cyclohexane-1,2-dicarboxylic acid and oxalic acid. A possible structure for the unknown compound is: