An unknown organic compound P has a molecular formula of CaH160. P reacts with 2,4- dinitrophenylhydrazine but not with Tollen's reagent. P also reacts with iodine in sodium hydroxide to give yellow precipitate. On reduction, compound P produces a new compound Q. On heating the compound Q with concentrated sulphuric acid produces R which decolourises bromine in tetrachloromethane. Identify P, Q and R. Explain your reasoning.

An unknown organic compound P has a molecular formula of CaH160. P reacts with 2,4- dinitrophenylhydrazine but not with Tollen's reagent. P also reacts with iodine in sodium hydroxide to give yellow precipitate. On reduction, compound P produces a new compound Q. On heating the compound Q with concentrated sulphuric acid produces R which decolourises bromine in tetrachloromethane. Identify P, Q and R. Explain your reasoning.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.60P

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