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2

The issue in this Grob fragmentation is whether or not the C-C and C-OTs bonds are antiperiplanar. The C-OH bond is free to rotate and the unpaired electrons of the negative oxygen can align with the other two bonds. In the first example a), the red bonds are gauche to one another. Standard E2 elimination is likely the source of the mixture. Examples b), c) ...


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Yes, E2 and SN2 are competing reactions. Keep in mind, E2 reactions require a base whereas SN2 reactions require a nucleophile. Nucleophilicity corresponds to the ability to donate a lone pair of electrons ‒ here, to a carbon bearing leaving group ‒ which is a kinetic property (time does matter). Basicity corresponds to accepting a hydrogen, a thermodynamic ...


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