Question

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2. (pts) The following transformations require 5-6 steps. Show how to accomplish the transformations below using benzene as the starting material and any other monounctional organic reagents and inorganic reagents. To maximize your chances for partial credit show the products obtained after each step. Mechanisms should NOT be included. Your best 1 of 2 will be graded. отьору OH

Answer 1

Benzene undergo nitration with nitrating mixture to form nitrobenzene which further undergo chlorination with chlorine and FeCl3 to form m-chloro nitro benzene. Then, nitro is reduced with Fe and ammonium chloride to form 3-chloroaniline. Further, hydrolysis of amine to hydroxyl group is carried by diazotization reaction. Finally, ethyl is formed by alkylation of phenol derivative in presence of K2CO3 and ethyl iodide to form 1-chloro-3-ethoxybenzene.

Benzene undergo formylation reaction with DMF and POCl3 to form benzaldehyde. Further reaction with chlorine and FeCl3 forms meta chloro benzaldehyde. Aldehyde group is reduced with NaBH4 and converted to Br using pBr3.Finally, benzyl bromide derivative reacts with Lithium metal and 3-pentanone to form final product. Here, lithium metal does not react with aromatic chloride.

NO2 NO2 NH2 OH m.mm.5 ora. Cam.co . En annen HNO3, H2SO4 Cl2, FeCl3 Fe, NHACI, Ethanol NaNO2, HCI H2O 3-chlorophenol benzene nitrobenzene 1-chloro-3-nitrobenzene 3-chloroaniline K2CO3, Ethyl iodide, DMF 1-chloro-3-ethoxybenzene OH DMF, POCIE NCS, CCIA NaBH4, THF PBrz, DCM Dr.- benzene benzaldehyde 3-chlorobenzaldehyde (3-chlorophenyl)methanol 1-(bromomethyl)-3-chlorobenzene НО, 3-(3-chlorobenzyl)pentan-3-ol