Tag: aromatic-compounds

organic chemistry – Is the ammonium substituent (-NH3+) really meta-directing in electrophilic substitution?

The Question : 25 people think this question is useful If we make a resonance structure for the anilinium ion, with positive charge at either the ortho or the para position, we get a pentavalent nitrogen, which is not possible. So, how is the $\ce{-NH3+}$ group meta-directing in electrophilic aromatic substitution reactions, e.g. in nitration

organic chemistry – Why is cyclooctateraene shaped like a “tub” rather than a “chair”?

The Question : 27 people think this question is useful I understand that for cyclooctatetraene (COT) to “escape” the horrible prospect of becoming an anti-aromatic molecule, it must adopt a non-planar conformation. The widely touted conformation of COT is said to be “tub” shaped. My sources (random links Google threw up) also concur on this

organic chemistry – Unusual Friedel–Crafts alkylation with pivaloyl chloride

The Question : 27 people think this question is useful In class we were told of an anomalous Friedel–Crafts reaction with a tertiary acid chloride — $\ce{(CH3)3CCOCl}$, or pivaloyl chloride. When this reacts with benzene in the presence of $\ce{AlCl3}$, instead of effecting the normal acylation, it instead breaks down into the tert-butyl carbocation, which

organic chemistry – Why does nitration of N,N-dimethylaniline occur at the meta position?

The Question : 45 people think this question is useful The nitration of N,N-dimethylaniline with $\ce{H2SO4}$ and $\ce{HNO3}$ gives mainly the meta product, even though $\ce{-NMe2}$ is an ortho,para-directing group. Why is this so? The Question Comments : en.wikipedia.org/wiki/Tetryl – reaction can proceed in other way The best way around this issue, from a reagent/yield