SP21 234 R20 Carbohydrates In Class PDF

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CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates

H

OH

HO H

H OH

O H

2

H HO H H

CHO OH H OH

HOH2C

OH CH2OH

O

1

CHO

O

O

O

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates 1. Convert Fisher Projection to chain form:

CHO HO H HO H

H OH H OH CH2OH

CHO H OMe

2

H MeO

OMe H

H

OH CH2OH

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates

CHO H OH HO HO H

MeO MeO H H

H H OH CH2OH

CHO H H OMe OH CH2OH

3

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates 2. Convert the Fisher projection of the open-chain form of each of the following molecules:

OMe OMe H

OH O

OMe OH

OH OMe O HO

H OMe OMe

4

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates 3. Convert chair conformation to the open-chain form of each of the following molecules:

OH O

HOH2C

OH OH

OH

OH

OH

O H3 C

OH

HO HO

OH H H OH

5

O

H

OH

H OH

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates 4. Predict the product for the following transformation.

HO H HO H

H OH H

H2O, H+

+

OH CH2OH α -pyranose form

H H

O OH OH

HO H

H OH

H2O, H+

β-pyranose form

+

CH2OH α -pyranose form

6

β-pyranose form

Prepared by Dr. Maria Yermolina

CHEM 234 • Organic Chemistry II Review 20 • Carbohydrates

OH

OH

O

HO

H3O+ H

OH

OH

OH

HO

1. H2O, H+ H

OH OH

+ 2. KH, 18-c-6, THF Br

Ph

α

7

β

Prepared by Dr. Maria Yermolina...