Chemistry 251

Aromatic Review Sheet

1. Using the textbook and class notes, show how the ollowing com!o"nds co"ld be synthesi#ed rom $%&'%&%. (o" are allowed to "se any reagents that we have covered in class. Ass"me that yo" can se!arate ortho and para isomers i needed. a) *+ethylben#enes"l onic acid b) ,+bromoaniline c) ,+chloroben#oic acid d) *+isob"tylc"mene e) 2+chloro+*+nitrotol"ene ) 1,,,5+trinitroben#ene 2. -raw all the resonance str"ct"res ormed when ethoxyben#ene is alkylated with ben#yl chloride. ./int0 i ortho/para s"bstit"tion is ex!ected, there will be 2 sets o str"ct"res.)
O CH2 CH3 CH2 Cl AlCl3

,. Using the s!ectral tables available, determine the identity o the com!o"nds rom textbook !roblems 12, 1,, 1* *. $e able to draw the ste!wise mechanisms or0 halogenation, nitration, alkylation, and acylation o an aromatic ring. 5. 2now the str"ct"res or0 ben#ene, tol"ene, c"mene, !henol, aniline, ben#aldehyde, ben#oic acid, ben#enes"l onic acid, ben#onitrile, aceto!henone.