9-Borabicyclo[3.3.1]nonane (9-BBN) is a reagent commonly
Chapter 9, Problem 9.88(choose chapter or problem)
9-Borabicyclo[3.3.1]nonane (9-BBN) is a reagent commonly used in the hydroboration of alkynes (Section 10.7), but it can also be employed in reactions with alkenes. The following table provides the relative rates of hydroboration (using 9-BBN) for a variety of alkenes (J. Am. Chem. Soc. 1989, 111, 14141418): Alkenes Relative Reactivity CH2 CHOBu, 1 1615 CH2 CHBu, 2 100 CH2 CHCH2OMe, 3 32.5 CH2 CHOAc, 4 22.8 CH2 CHCH2OAc, 5 21.9 CH2 CHCH2CN, 6 5.9 CH2 CHCH2Cl, 7 4.0 cis- 2-Butene, 8 0.95 trans-CH3CH2CH CHCl, 9 0.003 (a) Provide a structural explanation for the relative rates of reactivity for compounds 15. Be sure to explore resonance effects as well as inductive effects. (b) Provide a structural explanation for the relative rates of reactivity for compounds 5, 6, and 7. (c) Provide a structural explanation for the relative rates of reactivity for compounds 2, 8, and 9.
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