An organic compound C6H4N2O4 is insoluble in both dilute acid and base. Dipole moment of the compound is zero. Write the IUPAC name of the compound.
Submission Closed
Cracked By:
Ankul Garg, 12th, Delhi
T.R. Manoj, 12th, Hyderabad
Sooraj Prakash, 12th Pass, Bhopal
Harikrishna Devarajan, Chennai
Virgaonkar Waman, 12th, Nashik
Chandni Bhatia, 12th, Bhopal
Akshay Hattiangadi, 12th, Mumbai
Praveen Gorakavi, 12th Pass, Hyderabad
Answer: 1,4-dinitrobenzene
The following answer is the edited version of the explanations provided by Manoj & Sooraj:
As the D.U. is 6 and hydrogen to carbon ratio is less than 1, we expect the benzene ring (Huckel's rule satisfies this as well). As the above compound is insoluble in base, it means there is no acidic proton donor site, hence no phenolic or carboxylic acid group is expected in the side chain (in fact looking at the chemical formula, the side chain must have nitrogen and oxygen). Now as the above compound is insoluble in acid it means there is no basic site .i.e there is no lone pair on nitrogen available for donation. All these are possible in the case of nitro group. Also, intermolecular hydrogen bonding is ruled out as well (further cause for solubility). Finally, as the dipole moment is zero it means the molecule is symmetric.