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For questions involving selectivity as to where a functional group reacts.

2
votes
Well yes, a primary carbocation is more reactive than a secondary carbocation. But both are still so extremely reactive that they have lifetimes as short as is physically possible. Any reactions with …
answered Sep 18 '17 by Jan
2
votes
There have been tons of articles, review articles and even books written on the subject. The tl;dr version is that it depends on the conditions you use. In general, the less-hindered enolisation (in …
answered Nov 4 '17 by Jan
9
votes
The different reactivities of $\ce{KCN}$ and $\ce{AgCN}$ with alkyl halide, giving nitriles and isonitriles, respectively, has often been cited as a prime example of Pearson’s hard and soft acids and …
answered Aug 30 '16 by Jan
7
votes
The halogenation of toluene is possible by two mechanisms. In German, they are referred to by the shorthands KKK and SSS, where KKK stands for Katalysator, Kälte, Kern (catalyst, cold and core) while …
answered Jun 6 '16 by Jan
5
votes
First, let’s take a look at the radical chain reaction that leads to the substitution in question: $$\begin{align}\ce{Br^. + H-R &-> HBr + R^.}\tag{1}\\[0.4em] \ce{R^. + Br-Br &-> R-Br + Br^.}\tag{2} …
answered Dec 11 '16 by Jan
5
votes
I propose the route in the following scheme. I don’t see any unfavourable intermediates. In short, the first step would be formation of a Schiff base with the extracyclic amino group and the aldehyde. …
answered Jan 22 '17 by Jan
3
votes
Cyclohexene is very symmetric. At first approximation, you can draw two planes of symmetry: one containing the double bond and one orthogonal, bisecting the double bond. These two planes of symmetry …
answered Oct 4 '17 by Jan
8
votes
For the enolates that can be formed, the others have already given comprehensive answers: All four enolates are possible and since we are under thermodynamic control (weak base), we expect o observe t …
answered Dec 29 '15 by Jan