Mutarotation & Ring Formation + Examples - Lecture Notes - Edubirdie

University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

233

Pages:

2
Author:

Niklas

MutaRotation: Change in equilibrium between 2 anomers. HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH Pure α-anomer HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH α-anomer HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH β-anomer Ring Formation: CHO | H-C-OH | HO-C-H | H-C-OH | CH2OH HO-C-H | H-C-OH | HO-C-H | H-C-OH | CH2OH HO-C-H | H-C-OH | HO-C-H | H-C-OH | CH2OH Preferred! α-anomer HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH β-anomer HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH Haworth Projection HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH Examples: AcO | AcO-C-Cl | OAc Equilibrium shifts to right OAc | Cl-C-OAc | OAc (<2%) (>98%) Anomeric Effect Electronic effect wins over steric effect. Compare: MeO | MeO-C-X | OMe MeO | MeO-C-X | OMe X = -OH, -Br, -Cl, etc. Periplanar = same plane No extra stabilization - No overlap Extra Stabilization from overlapping orbitals

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