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)
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)
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 59AP
Related questions
Question
Question is attached. thank you
Transcribed Image Text: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)
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 1 images
Recommended textbooks for you
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning