p. 473 — since when is the C – C bond length 1.47 Angstroms? — I remember 1.54
p. 475 — Great to see actual physical evidence for the charge distribution in protonated benzene using 13C NMR (and on p. 485 for protonated toluene).
p. 479 — The fact that ortho and para positions are brominated in phenol, shows you that the symmetrical ring current in benzene isn’t the whole picture. The electron distribution is asymmetric as shown by the proton shifts in NMR (and elsewhere by the 13C shifts in NMR). It would be interesting to see the bond lengths between the ring carbons (I couldn’t find it).
p. 481 — How does concentrated nitric acid oxidize phenol (and to what does it oxidize it?).
p. 488 — What does FeBr3 look like? In the mechanism FeBr5- is written down (but not drawn out).
p. 489 — Poor overlap of the p orbitals of the halogens with the p orbital of carbon is mimicked in the following table (however these are sigma bonds, but the effect on p orbital overlap should be the same).
It’s also amusing, on reading the editorial and the paper, how little shrift organic chemists give to the Heisenberg uncertainty principle and quantum mechanics in general. This work is all about moving atoms and groups around in space, with the only uncertainty being how to make the reaction work. Ultimately, of course chemistry rests on QM — atoms of an element have the properties they do because their energy levels are fixed, and identical for all.
p. 491 — It would have been quite a digression for the text, but you should look up the structure of P2O5 (formed by burning elemental phosphorus). It comes in several forms one of which looks like adamantane (P40xygen10) with oxygens where the secondary carbons would be linking the 4 phosphorus atoms at what would be the 4 tertiary carbons of amantadine. In addition there are 4 oxygens coming off the 4 phosphorus atoms.
p. 509 — “The litthium cuprates (R2CuLi) that are formed are not stable” — what happens to them?
p. 512 — The cyanoimine shown in the inset doesn’t look ‘simple’ to me. How in the world is it made?
p. 513 — Does the alpha effect explain why Br2 is a better nucleophile than Br- (if in fact it is). Is this true for all halogens?
p. 519 — An 80 fold increase in rate is only a 4 fold decrease in activation energy. See p. 482 in these notes.