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Top and bottom temperatures of fractionating column:
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- HCN is highly toxic, so KCN/HCl is typically employed. Nitriles are precursors to amines/carboxylic acids
- amine attacks carbonyl group, oxygen protonated to remove negative charge, deprotonation gives a carbinolamine (H taken from the N), OH group protonated into a good leaving group, water leaves, C=N double bond forms, intermediate deprotonated to generate enamine
- so that the less hindered end of the double bond comes from the ylide