CABAǸAZ, KIRSTEN LUCILLE

MEMBREVE, MARIANE JAN

TAMBULE, PRETTY MARIE

BS – PSYCHOLOGY, LEVEL 2

CHY 43 ORGANIC CHEM WITH BIOCHEM

PROF. NELLIE C. LASTIMOSA
MW 4:00PM – 5:30PM

CASE STUDY NO. 2

AN ADVENTURE IN STEREOCHEMISTRY: ALICE IN MIRROR IMAGE LAND

I. INTRODUCTION

II. QUESTIONS AND ANSWERS

1. Professor Lime tells Alice that she could digest only one of the amino acids found
in Mirror Image Land (MIL). But couldn’t digest any of the proteins found there.
Which amino acid could Alice eat? If she can eat an amino acid, why can’t she
eat MIL proteins?
Alice could only eat glycine because it does not have a chiral carbon
and therefore does not have a “non-superimposable mirror image” which
is also known as enantiomer. If Alice ate proteins that consisted of amino
acids other than glycine, she could not digest them because she only has
enzymes that digests L-amino acid stereo-isomers and in MIL, the amino
acids are D-amino acids, an exact opposite of the latter.
2. In our world, starch is a polymer formed from a single monomer unit, D-glucose.
How would MIL starch differ from our starch? Draw the structure of the monomer
unit that would present in MIL starch.

H O O H
C C

HO C H H C OH

H C OH OH C H

HO C H H C OH

HO C H H C OH

CH2OH HO2HC
L-GLUCOSE MIRROR D-GLUCOSE

3. Professor Lime tells Alice that she could eat some MIL fats, but not others. We
will limit our consideration of fats to mono-, di-, and triglycerides that are formed
from glycerol and various achiral fatty acids. Assuming that the fatty acids
represented by the R-groups may be the same or different, and further assuming
that they are not themselves stereo genic (chiral), decide which glycerides (fats)
Alice could safely eat in MIL.
Alice could only consume the glycerides that do not comprise a chiral
carbon. Alice could eat any 2-monoglyceride or any 1, 2-diglyceride and
she could eta the 1, 3-diglycerides only when R is exactly the same as R’ –
non-chiral. In addition, Alice could only eat the triglycerides only when R
is exactly the same as R’’ – non-chiral.

4. The structure of carvone is shown, but its stereochemistry is not specified. Draw
the structures of two carvone enantiomers and correctly label each. Specify the
priorities that you have assigned to the groups attached to the stereo genic
carbon atom.
CH3 H3C
O O

C H H C
H3C CH2 H2C CH3
(-)-Carvone (caraway) (+)-Carvone (spearmint)
 5. The sweetener in the sugar-free gum that Professor gives to Alice is a
carbohydrate named xylitol. What can you say about the chirality of xylitol?
The sugar-free gum the professor gave to Alice is not good for her
because based on the structure of xylitol, it is found to have a one chiral
carbon on its bottom carbon on the ring.

6. Professor Lime cautions Alice that she must be careful what pain reliever she
chooses to take to relieve her headache. Shown in the case study sre the
structures of four commonly used analgesics. If we assume that only the mirror
image isomers of these compounds were available to Alice in MIL, which of these
compounds would be good choices for Alice to take?
Aspirin and Acetaminophen would be fine for Alice to take because
they have no chiral carbons.

7. Alice is confused when professor Lime tells her that she can breathe in MIL she
can eat anything that is “like our air”. He also includes water in the things that
Alice could use safely in MIL. Explain the Professor’s reasoning when he made
these statements to Alice.
Professor Lime made these statement to reason out that because Non
chiral molecules like that gas molecules in air would be fine for Alice’s
survival.

8. The Professor cautions Alice that she would be able to use some MIL vitamins,
but that others would not work for her. The structures of B-carotene and three
important vitamins are shown in the case study. Which of these could Alice use,
which would be ineffective for her in MIL?
The molecules with chiral carbons would be ineffective: Vitamin E and
Vitamin C.

III. SUMMARY
IV. REFERENCES