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Conformation cyclic cpds
1.
2. Conformation of cyclic compound
( viewed by Fisher and Haworth projections with
Chair conformations)
2 conformers of cyclohexane: boat and chair (more stable)
3. The 2 orientations of substituents in the CHAIR forms:
a) Equitorial = bonds that project outside along the plane of a ring
b) Axial = bonds that project above and below the plane or perpendicular
to the plane
Note: equatorial bonds are more stable than axial due to less steric
hindrance - the more bulky groups on the equatorial, the
more stable
4.
5.
6. CONVERTING FISCHER PROJECTIONS OF “D”
MONOSACCHARIDES INTO HAWORTH STRUCTURES
1. The hemiacetal carbon is the carbon where the C=O found
2. All of the atoms on the right in Fischer are pointed down in the Haworth structure.
3. All of the atoms on the left in Fischer are pointed up in the Haworth structure.
4. The CH2OH (the carbon-#6 in D-glucose) is pointed up in the Haworth structure
5. The OH attached to carbon-#5 (box around it) becomes part of the ring.
6. The linear Fischer projection becomes a cyclic hemiacetal in the Haworth structure.
7. The hemiacetal Carbon-1 “*” is the anomeric carbon in the Haworth
