- Propose syntheses of the following compounds from benzene: (a) N,N-Dimethylaniline (b) p-Chloroaniline (c) m-Chloroaniline (d) 2,4-Dimethylaniline
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- When pyrrole is added to a dilute solution of D2SO4 in D2O, 2-deuteriopyrrole is formed. Propose a mecha-nism to account for the formation of this compound.Give a rearrangement reaction equation to synthesize N-ethyl-2-methyl-buthylamide from the corresponding α-diazoketone. Give the structures of all intermediary products. Do not give a mechanism.One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.
- Give the expected products of lithium aluminum hydride reduction of the followingcompounds (followed by hydrolysis).(a) butyronitrile (b) N-cyclohexylacetamide (c) e@caprolactamGive the expected products of lithium aluminum hydride reduction of the followingcompounds (followed by hydrolysis).(a) butyronitrile (b) N-cyclohexylacetamidePropose a mechanism to account for the following finding:
- In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?Indicate the order of basicity of: aniline, 2-propylamine and 1-(2-aminophenyl)ethanone. Explain.a) Write a mechanism for the formation of semicarbazone Y.b) Explain why formation of imine Z is not favoured.
- Suggest ways of synthesizing the following compounds, how would youmake the disconnections and what are the synthons?Compound A has the molecular formula C14H25Br and was obtained by thereaction of sodium acetylide with 1,12-dibromododecane. On treatment ofcompound A with sodium amide, compound B (C14H24) was obtained. Ozonolysisof compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation ofcompound B over Lindlar palladium gave compound C (C14H26), andhydrogenation over platinum gave compound D (C14H28). Further, C yieldedO=CH(CH2)12CH=O on ozonolysis. Assign structures to compounds A through Dso as to be consistent with the observed transformations.When N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three products