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Organic Chem

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CHEM 232
1.

Organic Chemistry II

Problem Set 12

Identify each of the following compounds as reducing or nonreducing sugars:
H HO HO H HO CH2 O H OH H CH2OH OH B Nonreducing sugar (acetal) CHO H H E OH OH CH2OH CHO OH OH OH CH2OH H H G OH HO CH2OH O H H H OCH2CH3 H HO H OH OH CH2OH O H H H OH CH2 O C OH H CH2OH H OH H

H

O

H HO A

Reducing sugar (hemiketal)

Nonreducing sugar (acetal and ketal) CH2OH C O OH OH CH2OH

CH2OH HO OH H

O H

CH2OH H

H H H F

OH D

Reducing sugar (hemiketal)

Reducing sugar (aldose)

Reducing sugar (aldose)

Reducing sugar (ketose)

2.

Which of the structures shown above are: a. Pyranose monosaccharides A and B b. Furanose monosaccharides D c. Tetroses E d. Aldopentoses F e. Ketopentoses G f. Disaccharides C

3.

Give the Haworth formula for α-D-Glucopyranose.
H HO H OH CH2OH O H H OH H OH

4.

Complete the following reactions:
a. CH3CH2CH(OH)CH2OH b. O HOCH2 C CH2OH HIO4 CH3CH2CHO

+ CH2=O
OH O O

AgNO3-NaOH NH3

HOCH2 CH C

Ag0

OH HOCH2 C
c. H H CHO OH OH CH2OH HIO4 3 HCO2H

OH CHOH HOCH2 CH C
d.

O H
CHO H H OH OH CH2OH HCN CN H H H OH OH OH CH2OH HO CN H OH OH CH2OH

+ CH2=O

+

H H

e. H HO H

CHO OH H OH CH2OH

NaBH4 H2O

H HO H

CH2OH OH H OH CH2OH
h. H HO

f. HO H H

CHO H OH OH CH2OH

CHO 1. Br2/H2O 2. H2O2 Fe2(SO4)3 H H OH OH CH2OH

g. CHO H OH H H OH OH CH2OH 3 PhNHNH2

CH NNHPh C H H NNHPh OH

CH2OH O H H H OH OH

H OH

CH3OH H+

H HO

CH2OH O H H H

OCH3

OH CH2OH Osazone

OH OH Acetal (mixture of anomers)

5.

For the structrures shown below: a. Which structure is an L-sugar? Answer: X b. Which structure is an epimer of Y?
CHO H OH OH CH2OH CHO H OH H CH2OH CHO OH OH OH CH2OH CHO H H OH CH2OH

Answer: W

HO H H W

HO H HO X

H H H Y

HO HO H Z

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