Structure and Reactivity
Paracetamol consists of a benzene ring core, substituted by one hydroxyl group and the nitrogen atom of an amide group in the para (1,4) pattern. The amide group is acetamide (ethanamide). It is an extensively conjugated system, as the lone pair on the hydroxyl oxygen, the benzene pi cloud, the nitrogen lone pair, the p orbital on the carbonyl carbon, and the lone pair on the carbonyl oxygen are all conjugated. The presence of two activating groups also make the benzene ring highly reactive toward electrophilic aromatic substitution. As the substituents are ortho, para-directing and para with respect to each other, all positions on the ring are more or less equally activated. The conjugation also greatly reduces the basicity of the oxygens and the nitrogen, while making the hydroxyl acidic through delocalisation of charge developed on the phenoxide anion.
Read more about this topic: Paracetamol
Famous quotes containing the words structure and and/or structure:
“Slumism is the pent-up anger of people living on the outside of affluence. Slumism is decay of structure and deterioration of the human spirit. Slumism is a virus which spreads through the body politic. As other “isms,” it breeds disorder and demagoguery and hate.”
—Hubert H. Humphrey (1911–1978)
“Women over fifty already form one of the largest groups in the population structure of the western world. As long as they like themselves, they will not be an oppressed minority. In order to like themselves they must reject trivialization by others of who and what they are. A grown woman should not have to masquerade as a girl in order to remain in the land of the living.”
—Germaine Greer (b. 1939)