JEEMOCKSby Edzok
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Organic Compounds Containing Oxygen

Migratory aptitude disregarded

What goes wrong

Selects a migrating group without checking carbocation stability or migratory aptitude order.

Next time

Check for 1,2-shifts by comparing potential carbocation stabilities and migrating the best group following the H−>Ph−>alkyl−\text{H}^- > \text{Ph}^- > \text{alkyl}^- aptitude order.

Questions that set this trap

1 published question

Exhaustive aldol substitution stopped early Ester assumed more reactive than anhydride Ketone assumed more reactive than aldehyde HVZ halogenation regiochemistry misplaced Conjugation ignored in elimination regiochemistry Ether hydrogen bonding capacity ignored