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- Final exam scheduling opens Wed., 22nd of April 10:10 am. Deadline 26th of April at 11:55 pm.- Two sessions May 1st: session 1: 8-10 am
session 2: 6:00-8:00 pm
-If you have a conflict, bring me form from registrar office.
-Final is cumulative and it will cover all chapters including chapter 25 (carbohydrate).
-OWL deadline
- practice exams
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Mechanisms included in the final exam
Grignard reaction with carbonyl mechanism (Ch 19) Wittig reaction mechanism (Ch19) NaBH4 reaction with ketone/aldehyde mechanism (Ch 19) Fischer esterification mechanism (Ch 20) Basic epoxide ring opening mechanism (Ch 18) -Enol formation (tautomerization) under basic conditions (Ch 22) -Enol formation (tautomerization) under acidic conditions (Ch 22) - Aldol condensation rxn (Ch 23) -Claisen condensation rxn (Ch 23) 1,2 and 1,4 addition mechanism (Ch14)
- Electrophilic Aromatic substitution mechanism (Ch 16)
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Cyclic Structure
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Furanose: A five member cyclic hemiacetal form of a monosaccharide.
Pyranose: A six member cyclic hemiacetal form of a monosaccharide.
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Haworth Projections
-Anomeric carbon: the hemiacetal carbon of the cyclic form of a monosaccharide.-OH groups on the left in Fischer projection are in the upper face of the ring.- For D sugars(CH2OH) on last stereocenter is on the top face of the ring
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Number the carbons in the Fischer projection.
Draw pyranose with oxygen to the back. Anomeric carbon (carbon that used to have C=O) in the right front.
Draw OH groups on the left in Fischer projection in the upper face of the ring. (Right down)
For D sugars, the CH2OH on the last stereocenter (carbon 6 in an aldohexoses) should be on the top face of the ring.
The hemiacetal carbon is chiral. Formation of two anomers alpha and beta.
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means that the -OH on the anomeric carbon is on the same side of the ring as the terminal -CH2OH.
means that the -OH on the anomeric carbon is on the side of the ring opposite from the terminal -CH2OH.
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HO
HOCH2 OH
HHO
CH2OH
OHH
H
C=O
CH2OH
HOH
CH2OH
OHH
HO HOH
HOHOCH2
HO HCH2OH
OH
D-Fructose
1
2
5
5
5
1
2
2
()
-D-Fructofuranose(-D-Fructose)
-D-Fructofuranose(-D-Fructose)
()
1
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Which of the following is a beta-furanose Haworth projection?
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Which of the following is an alpha-furanose Haworth projection?
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Draw the Haworth projection(s) of alpha anomer of D-galactopyranose.
A B
C D
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Draw the chair conformation of the alpha anomer D-galactopyranose.
A B
C D
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