Newman Projection - Lecture Notes | York University - Edubirdie

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

2023
Views:

399

Pages:

4
Author:

Niklas

Newman Projection: *Gauche B H No Overlap! *Overlap! H How do α and β anomers convert in acidic solution? Example: 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 Mechanism: HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH Protonate anomeric carbon! HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH H2O can attack from the top or the bottom! HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH α HO-CH2OH | H-C-OH | HO-C-H | H-C-OH | CH2OH β Effect of 1/2 Chair on Selectivity HO | HO-C-H | HO-C-H | H-C-OH | CH2OH HO | HO-C-H | HO-C-H | H-C-OH | CH2OH Equatorial Preferred! HO | HO-C-H | HO-C-H | H-C-OH | CH2OH Axial High NRG! Strong 1,3-diaxial interaction

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