Answered: 8. When (1R,2R)-2-bromocyclohexanol is… | bartleby

Organic Chemistry

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

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8. When (1R,2R)-2-bromocyclohexanol is treated with NaOH, the product does not exhibit a
broad IR stretch at 3000-3500 cm³¹ and does not rotate plane polarized light. However, when
(1R,2S)-2-bromocyclohexanol is treated with NaOH, the product exhibits a strong, broad IR
signal at 3000-3500 cm³¹, and is found to be optically active. Draw the two starting materials and
propose a mechanism for their reactions with NaOH that is consistent with these observations.
(16 pts)

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