When 1-methylcyclohexene undergoes hydration in D₂O, the product is a mixture of diastereomers; the hydration is thus not a stereoselective reaction. (See Fig. P7.57)

(a) Show why the accepted mechanism for this reaction is consistent with these stereochemical results.

(b) Why must D₂O (rather than H₂O) be used to investigate the stereoselectivity of this addition?

(c) What isotopic substitution could be made in the starting material, 1-methylcyclohexene, that would allow investigation of the stereoselectivity of this addition with H₂O?

Transcribed Image Text:

CH3 Figure P7.57 + D₂0 H₂C LOD ~·¢ 'H D D30+ OD LCH3 D "H both compounds are racemates