# Tag: aromatic-compounds

## everyday chemistry – Why are smoke odors persistent in fabrics?

The Question : 25 people think this question is useful Obviously smoke is very complex, but apparently phenol compounds are the main components of wood smoke that produce the characteristic odor. (One of more significant of these compounds seems to be syringol.) The human nose seems to be pretty sensitive to these compounds. Smoke seems

## 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

## IUPAC nomenclature for an interesting looking organic compound

The Question : 35 people think this question is useful How can I name this organic compound while adhering to the IUPAC standards? The Question Comments : Congratulations! This structure breaks my favorite structure editor (ChemDoodle) when I attempt to have it name this molecule… Congratulations, this structure breaks ChemDraw’s structure-to-name feature too! I’ll try

## organic chemistry – Mechanism of arene side chain oxidation by permanganate

The Question : 40 people think this question is useful When treated with hot, concentrated acidic $\ce{KMnO4}$, arenes are oxidised to the corresponding carboxylic acids. For example, toluene is oxidised to benzoic acid. I’ve tried to examine how this happens, using the mechanism of oxidation of double bonds via cyclic intermediate as a reference, but

## 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