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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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