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Magazine Chapter 19: Q25P (page 1014)
Show how you would convert aniline to the following compounds
(a)flurobenzene (b) chlorobenzene
(c) 1,3,5- trimethylbenzene(d) bromobenzene
(e) iodobenzene(f) benzonitrile
(g) phenol
(h)
Short Answer
(a)
(c)
(d)
(e)
(f)
(g)
(h)
Step by step solution
Aniline to fluorobenzene
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to give benzene diazonium salt. This compound is reacted to HBF4to give flurobenzene.
(a)
Aniline to chlorobenzene
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to give benzene diazonium salt. This compound is reacted to Cu2Cl2 to give flurobenzene. This is the Sandmeyer step.
Aniline to 1,3,5- trimethylbenzene
At first aniline is reacted methyl iodide in presence aluminium trichloride then reacted to NaNO2/ HCl at 0o C temperature to give 1,3,5- trimethyldiazonium salt. This compound is reacted to H3PO3heat to give 1,3,5-trimethylbenzene.
Aniline to bromobenzene
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to give diazonium salt. This compound is reacted to CuBr and HCl to give bromobenzene.
Aniline to iodobenzene
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to givediazonium salt. This compound is reacted to KI to give iodobenzene.
Aniline to benzonitrile
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to givediazonium salt. This compound is reacted to CuCN to give benzonitrile.
Aniline to benzene
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to givediazonium salt. This compound is reacted to HBF4 to give benzene.
Aniline to (E)-4-(phenyldiazenyl)benzene-1,2-diol
At first aniline is reacted to NaNO2/ HCl at 0o C temperature to givediazonium salt. This compound is reacted to HBF4 benzene-1,2,4-triol to give (E)-4-(phenyldiazenyl)benzene-1,2-diol.
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