Marked similarities exist between the mechanism of nitrous acid deamination of B-aminoalcohols and the pinacol rearrangement. Following are examples of each. Nitrous acid NH, NANO, HCI =O + Ng + H,O deamination of a B-aminoalcohol: `OH OH H,SO4 Pinacol СНО + H,О rearrangement: HO,

The bicyclo [3.1.0] hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One method for preparing this ring system involves the conversion of compound 1 to compound 2, as shown below. Draw the structure of compound 2 and provide a reasonable mechanism for its formation. Add any remaining curved arrows to complete step one of the mechanism, and modify the given drawing as needed to show the intermediate that is formed in this step.

Select the major product from the reaction sequence shown. 1) MezNH, [TSOH], - H2O 2) 3) HO مال منه NMez .OH ? ka ta

Please provide a detailed mechanism for the following transformation. Also, show the appropriate curved arrows to rationalize the next step. The quality of the electron pushing counts.