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Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. [3] It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.
However, another effect that plays a role is the +M effect which adds electron density back into the benzene ring (thus having the opposite effect of the -I effect but by a different mechanism). This is called the mesomeric effect (hence +M) and the result for fluorine is that the +M effect approximately cancels out the -I effect.
Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline.
Heteroarenes are aromatic compounds, where at least one methine or vinylene (-C= or -CH=CH-) group is replaced by a heteroatom: oxygen, nitrogen, or sulfur. [3] Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one ...
Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene. Simple monocyclic aromatic rings are usually five-membered rings like pyrrole or six-membered rings like pyridine.
The fluorine atom is para with respect to the substituent Z in the benzene ring. The image on the right shows four distinguished ring carbon atoms, C1, C2, C3, C4 in p-F-C 6 H 4-Z molecule. The carbon with Z is defined as C1(ipso) and fluorinated carbon as C4(para). This definition is followed even for Z = H.
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As it generally begins with nucleophilic attack by the aromatic group, the electron density of the ring is an important factor. Some aromatic compounds, such as pyrrole, are known to formylate regioselectively. [6] Formylation of benzene rings can be achieved via the Gattermann reaction and Gattermann-Koch reaction.