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

10
votes
2answers
Secondary allylic halides can be produced in high yield with the following Mitsunobu-type reaction:[1] The yield being $94~\%$. The last step in the mechanism is: Why is the $\mathrm{S_N2}$ reac …
asked Feb 16 '15 by RBW
5
votes
0answers
Why does the Ziegler–Natta polymerization display the regioselectivity shown in the image? Internal nucleophiles (coordinated to the metal) should attack the alkene on the less substituted end, like …
asked Jun 29 '15 by RBW
8
votes
1answer
Why does benzofuran react preferentially at position 2 when nitrated or formylated, while indole reacts preferentially at position 3 (source: Joule and Mills, Heterocyclic Chemistry 5th ed., p 371)? …
asked Oct 5 '15 by RBW
14
votes
1answer
In the electrophilic aromatic substitution (EAS) of pyrrole, why is the alpha position preferred over the beta position so much?
asked Feb 28 '15 by RBW