Adapted from PLTL

Chem 227/ Dr. Rusay

Turn in answers to the questions only on the form provided.

Carbohydrates
1. Reminder: A Fischer projection is a way of representing 3-D molecules on 2-D surfaces. As in all
conventions, there are specific rules to be obeyed. (R)-Glyceraldehyde is the simplest monosaccharide.
Convert the 3-D representation into a Fischer projection formula.
H

HO CH 2OH
HC O

(R)-(+)-glyceraldehyde
2. Refer to: http://ep.llnl.gov/msds/orgchem/Chem227/naming.html

a. Draw a Fischer projection formula or Haworth formula for each of the six compounds.

b. Name each carbohydrate: detailed generic or precise names accepted. Clearly identify any that are
not "carbohydrates".

c. For each of the models that are carbohydrates, indicate if it is a mono-, di-, or polysaccharide and if
it is a reducing or a non-reducing sugar.

3. Provide structures that satisfy the following descriptions:

a. The aldopentose that would give the same aldaric acid as D-arabinose upon oxidation with nitric
acid.

b. The aldohexose that gives an optically inactive aldaric acid upon treatment with nitric acid and
gives D-ribose on sequential treatment with (i) Br2, H2O, and (ii) Fe2(SO4)3, H2O2.

c. The enediol that is an intermediate in the isomerization of the carbonyl group of D-arabinose from
the 1-position to the 2-position in aqueous base.

4. Provide structures for the major organic products of the following reactions:

CH3O OCH3
O H3O , H2 O
a. (give Fischer projection)
CH3O OCH3
OCH3

CH3 CH2OH
b. D-mannose (give chair conformation of product(s))
cat H3 O

NaBH 4
c. D-glucose (draw Fischer projection)
H2O
 Adapted from PLTL

O
2 H 3C CH3
a primary alcohol, C12H 20O6
d. D-glucose
(give chair conformation)
cat H3 O

CHO
H OH
1. HCN, CN
e. HO H
H OH 2. H3O , H2O, !
3. H2, Pd(BaSO4)
CH2 OH
4. H3O , H2O
 Adapted from PLTL

5. Optically active carbohydrate A (C14H20O7) does not react with Cu(II) complex (indicates an
aldehyde is not present), and upon treatment with dilute HCl gives optically active carbohydrate B
(C7H14O7) plus benzyl alcohol. Reaction of A with excess dimethyl sulfate gives C, which upon
dilute acid hydrolysis gives the optically active 2,3,5,6,7-pentamethyl aldoheptose D. When B is
treated with nitric acid, optically inactive E is formed. Oxidative removal of C1 of B gives D-glucose.
Give structures A through E consistent with this information.

Cu+2 (complex)
no reaction
H2O, OH

dil. HCl
A C14H20O7 B (C7 H14O7) + CH2 OH
optically active H2O optically active

O CHO
CH3 OSOCH3 CHOMe
O CHOMe
dil. HCl
C D = CHOH
–OH/H
2O
H2O optically
active CHOMe
CHOMe
CH2 OMe
HNO3 optically
B E inactive
H2O

CHO
H OH
HO H
1. Br2/H2O
H OH
2. Fe 2(SO4)3/H2 O2
H OH
CH2 OH

D–glucose
 Adapted from PLTL

6. Complete the Wordsearch on the turn in form.

7. Refer to: http://ep.llnl.gov/msds/orgchem/Chem227/naming.html

II.a) Select two planets that reflect the proportional difference between the size of a glucose molecule relative to
a virus.

b) Select three planets that reflect the proportional difference between the respective sizes of a virus, a
bacterium and a red blood cell.

c) How many glucose molecules could be contained within: i) the space of a virus and ii) the space of a red
blood cell?

(V = 4.189 r3) Show your respective calculations.