The compound shown is nitrated with one equivalent of HNO3 and H2SO4 (introducing a second nitro group). Which structure is the major product?

MolSynapse / Question bank / Organic Reaction Mechanisms II: Electrophilic and Radical Reactions / EAS major product and directing effects in drawn benzenes

JEE Advanced levelSingle correct optionDifficulty 3 of 3o2268

The compound shown is nitrated with one equivalent of $HNO X_{3}$ and $H X_{2} SO X_{4}$ (introducing a second nitro group). Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: D

The compound is 4-nitrobiphenyl. The ring carrying the nitro group is strongly deactivated, whereas the other ring is activated slightly by the aryl substituent, so the second nitration occurs on the unsubstituted ring. The phenyl-type substituent directs ortho/para and the para position is less hindered, giving 4,4'-dinitrobiphenyl.

Practice Organic Reaction Mechanisms II: Electrophilic and Radical Reactions More on EAS major product and directing effects in drawn benzenes

Previous questionNext question

The compound shown is nitrated with one equivalent of HNOX3​ and HX2​SOX4​ (introducing a second nitro group). Which structure is the major product?

Answer: D

More questions on EAS major product and directing effects in drawn benzenes

The compound shown is nitrated with one equivalent of $HNO X_{3}$ and $H X_{2} SO X_{4}$ (introducing a second nitro group). Which structure is the major product?