Marked similarities exist between the mechanism of nitrous
Chapter 23, Problem 23.37(choose chapter or problem)
Marked similarities exist between the mechanism of nitrous acid deamination of b-aminoalcohols and the pinacol rearrangement. Following are examples of each. NaNO2 NH , HCl 2 OH "O N 1 12 H2O Nitrous acid deamination of a -aminoalcohol: H2SO4 OH Pinacol 1 H2O rearrangement: OH CHO (a) Analyze the mechanism of each rearrangement and list their similarities. (b) Why does the fi rst reaction, but not the second, give ring expansion? (c) Suggest a b-aminoalcohol that would give cyclohexanecarbaldehyde as a product.
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