Question

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4. If (R)-2-bromo-3-methylbutane were to react with water, describe reaction conditions of how the achiral compound 2-methylbutan-2-ol would form. Draw the mechanism. 5.Put the following three compounds in order of increasing basicity. OH OH OH 6.What type of reaction happened if 3-chlorohexane reacted with water to form hexan-3-ol given the following chart and why? Draw the mechanism. Angle of light rotation as reaction proceeds 130 105 80 55 30 5 -20 45 -70 -95 -120 0 1 2 3 5 6 7 8 9

Answer 1

4 H₂C ram C BV 4 back the (=R (R)-2-bromo-3-methylbutane CH3 CH3 CH3 Haf 2 Carbocation & H-migration le CH3 (H - migration occure because 3° Carbo Cation is more stable 3° Carbo Cation | H2O I H CH3 H₂C H Carbocati than 2 combocation) Holt CH3 CH3 H H Atz -CH₃ H₂C OH (2-methylbutan-2-01 OH - ta CH3 City Product
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