Question

A compound 1 (C6H12Br), on reaction with magnesium turnings in diethyl ether followed by carbon dioxide, furnished 2 (CH1402) on work-up. Product 2 reacted with excess ammonia in methanol to yield 3 (C-H5NO), which was degraded by alkaline sodium hypobromite to 4 (C6H5N) with the evolution of carbon dioxide. Treatment of 4 with excess iodomethane in diethyl ether gave a crystalline solid 5, which, on heating with moist silver(II) oxide, furnished 1-hexene. Identify substances 1-5 and rationalize the conversions taking place.

Answer 1

Mg CO2 NaObr excess CH3l, Ago Compound 4 1-hexene Compound 1 CH3BT Compound 2 C7H1402 Compound 3 C7H150N CHIEN Lets take the reverse route of formation when an amine is treated with alkyl halide and silver oxide it forms an alkene. Therefore following reaction takes place O Ag20 -ZO CH31 excess NH2 hexan-1-amine Chemical Formula: C&H5N Compound 4 hex-1-ene Amines can be obtained by hoffmann degradation method by using NaOBr Therefore following reaction occurs NH2 NaOBr heptanamide 6 Chemical Formula: C7H15NO Compound 3 Hoffman degradation NH2 hexan-1-amine Chemical Formula: C&H5N Amide can be synthesized using excess ammonia reactino with acid OH NH2 heptanoic acid © heptanamide 6 Chemical Formula: C7H1402 Chemical Formula: C7H15NO Compound 2 Acid was obtained by addition of grignard reagent on CO2 which was prepared by using alkyl halide Br Mg, ether CO2 Mg, etherm OH MgBr – 1-bromohexane Chemical Formula: CH 13Br Compound 1 heptanoic acid 6 Chemical Formula: C7H1402