Name Group 3

Ilagan, Lineses, Maderazo, Mercado

ACTIVITY Section Schedule Monday
4 Introduction to Stereochemistry Q1A2
Instructor Date 03/18/19
Sir Edu Gonzales

ACTIVITY 4
Introduction to Stereochemistry

Pre-Lab Questions

Define the following:

a. Structural Isomer - any of two or more compounds with identical chemical

formulas, such as propyl alcohol and isopropyl alcohol, that differ structurally in the
sequence in which the atoms are linked. Structural isomers do not exhibit the same
chemical behavior.
b. Geometric Isomer - each of two or more chemical compounds having the same
molecular formula but a different geometric arrangement, an unsaturated
compound or ring compound in which rotation around a carbon bond is restricted,
as in cis- and trans- configurations.
c. Chiral center - Chiral centers are tetrahedral atoms (usually carbons) that have
four different substituents. Each chiral center in a molecule will be either R or S.
d. Achiral center - a molecule is a achiral if it is superimposable on its mirror image.
Most achiral molecules do have a plane of symmetry or a center of symmetry.
e. Asymmetric Carbon - is a carbon atom that is attached to four different types of
atoms or groups of atoms.
f. Polarimeter - is a scientific instrument used to measure the angle of rotation
caused by passing polarized light through an optically active substance.
g. Racemic mixture - is one that has equal amounts of left- and right-handed
enantiomers of a chiral molecule.
h. Stereochemistry - the branch of chemistry concerned with the three-dimensional
arrangement of atoms and molecules and the effect of this on chemical reactions.
i. Chirality -is a geometric property of some molecules and ions. A chiral
molecule/ion is non-supposable on its mirror image. The presence of an
asymmetric carbon center is one of several structural features that induce chirality
in organic and inorganic molecules.
j. enantiomer -optical isomers or each of a pair of molecules that are mirror images
of each other.
I. INTRODUCTION
Stereochemistry refers to the branch of Chemistry which deals with the
spatial arrangement of atoms and groups in molecules. The study of
stereochemistry focuses on stereoisomers, which by definition have the same
molecular formula and sequence of bonded atoms (constitution), but differ in
the three-dimensional orientations of their atoms in space. Stereochemistry
spans the entire spectrum of organic, inorganic, biological, physical and
especially supramolecular chemistry.
Stereochemistry includes methods for determining and describing these
relationships; the effect on the physical or biological properties these
relationships impart upon the molecules in question, and the manner in which
these relationships influence the reactivity of the molecules in question
(dynamic stereochemistry). Louis Pasteur could rightly be described as the first
stereo chemist, having observed in 1842 that salts of tartaric acid collected from
wine production vessels could rotate plane polarized light, but that salts from
other sources did not. This property, the only physical property in which the two
types of tartrate salts differed, is due to optical isomerism.
Molecular structures are so frequently represented in two dimensions that
we often experience considerable difficulty in thinking about molecules in three
dimensions. The purpose of this exercise is to train the student of organic
chemistry to think in three dimensions. The exercise is designed so that there
is a gradual step by step introduction to the basic concepts of stereochemistry.
Before you start you must be able to:
a. write and interpret molecular and structural formulas
b. recognize that the compound with a particular Lewis structure can exist
in a number of different forms called stereochemical isomers

Throughout the activity, you will actively participate in the learning

process by answering questions and constructing and inspecting molecular
models.
II. OBJECTIVES

a. To be able to construct three-dimensional models of molecules and

translate them to two-dimensional representations (drawings) and
vice versa.
b. To be able to determine chirality of molecules in terms of:
a. Superimposability / non-superimposability with a
corresponding mirror image.
b. Presence / absence of a simpleelement of symmetry like a
plane of symmetry.
c. Presence / absence of chiral centers
d. Presence / absence of optical activity
c. To be able to predict the existence of enantiomerism and
diastereomerism in certain compounds.
d. To be able to differentiate:
a. Enantiomers and a racemic mixture
b. Enantiomers and diasteroisomers
e. To recognize that:
a. free rotation about C – C single bonds gives rise to different
conformations
b. conformations are continuously and rapidly interconverting
c. there is a preferred conformation
f. To be able to differentiate between conformational and
configurational stereoisomers
III. Materials
Plastic balls of different colors, sticks, small mirror, pencil, drawing paper
IV. Procedure
V. Data and Results
Questions:
1. Determine whether each of the following pairs of objects are identical with
each other, i. e., superimposable:
a. Two forks
b. Your left hand and your right hand
2. View your right hand in front of the mirror.
a. Is the reflection of your right hand superimposable on your left hand?
b. Is your right hand the mirror image of your left hand?
3. Using a mirror, decide whether the following objects are superimposable on
their mirror images:
a. A fork
b. A pentagon
c. Your left hand
4. A plane of symmetry is an imaginary plane or sheet that divides the object
so that one half is the exact reflection of the other half. Determine whether
each of the following has at least one plane of symmetry:
a. A sphere
b. A regular tetrahedron
c. A shoe
5. Determine whether the objects in no. 4 are superimposable on their mirror
images or not.
6. Describe the relationship between the presence of a plane of symmetry in
an object and the object’s superimposability on its mirror image/

a. Construct the mirror image of the object. If the mirror image is identical to
the object, or is, superimposable, then the object is ACHIRAL. Otherwise, it is
chiral.

b. Inspect the object for the presence of a plane of symmetry. If it has a plane
of symmetry, then the object is ACHIRAL. Otherwise, it is chiral.

7. Construct a model of CH4. Is it chiral or achiral? Why?

8. Construct a model of CBrFClK. Is it chiral or achiral? Why?
9. a. Are enantiomers chiral?
b. Do enantiomers have the same molecular formula?
c. Does one structural formula represent both members of a pair of
enantiomers?
10. Are enantiomers steroisomers?
11. Determine whether each of the following is optically active:
a. CH3CH(NH2)COOH
 b. CH3CH2CHClCH3
c. CH3CH2CH2CH3
12. Which enantiomer of alanine rotates the plane of polarized light clockwise?
13. Substances which do not rotate the plane of polarized light are said to be
optically inactive. Which of the following aqueous solutions are likely to be
optically inactive?
a. A solution of ethanol, CH3CH2OH
b. A solution of (+) alanine
c. A solution of (-) alanine
d. A solution containing equimolar quantities of (+) alanine and (-)
alanine
14. Consider the following structural formulas:

H Cl

H3 – C – COOH H3 – C – CH2Br

OH Cl

a b
Which of the two contains a chiral center? Mark the chiral center with an
asterisk (*).

15. Which of the above is a chiral molecule? Explain your answer.

16. a. Which of the above can exist as a pair of enantiomers?
b. Draw the pair of enantiomers.
17. a. How many chiral centers does it have?
b. Mark the chiral centers with asterisks.
c. Copy the structure and encircle the four groups which are attached to
each chiral carbon.
18. Construct a model of ethane CH3CH3. Rotate the C – C single bond.

a) Is there a change in the relative positions of the different atoms?

 b) Does the ethane molecule have more than one conformation?
c) Draw the conformations of an ethane molecule
d) In which of the two extreme conformations are the hydrogens farthest
apart from each other?
19. Construct a model of 1,2 – dibromoethane, BrCH2CH2Br. Examine possible
conformations of this molecule. Which of the following interactions will be
the greatest?
a) H – H interactions
b) H – Br interactions
c) Br – Br interactions
20. Construct a model of the cyclohexane molecule (C6H12).
21. In which conformations are the hydrogens farthest apart?
22. . Mark the axial bonds with white sticks. Hold carbon atoms 1, 2, 3, 5 and
6 firmly and flip up C4. What conformation results?
23. Then holding carbons 2, 3, 4, 5 and 6 firmly, flip down C1. What
conformation results?

1. a. 2. a. Yes 3. a. Superimposable
Superimposable b. Yes b. Superimposable
b. Not c. Not superimposable
superimposable

4. a. Yes 5. a. Superimposable 6. With the phone symmetry being

b. Yes b. Superimposable present, that means that the object is
c. Yes c. Not superimposable super imposable and that is because
one half of the object is exactly a
reflection of the other half. This results
to the mirror image being align with all
the parts of the objects.
 7. Archiral because it is
superimposable on tits mirror image.
8. Chiral

9. a. Yes 10. Yes 11. a. optically active

b. Yes b. optically active
c. No c. optically inactive
13. 14. Both A and B
12.(+)- Alanine a. optically active
b. optically active 15. A.
c. optically active
d. optically active
16. 17. 18.
a. A a. 3 a. Yes
b. b. b. Yes
c.

c.

d. Eclipse

19. a. 20. No, cyclohexane has

no flat form.

b. H – Br
Interactions
21. Chair 22. Chair Conformation 23. Chair Conformation
Conformation
(staggered)

VI. Conclusion
First thing the researchers learned about this activity is how to determine
chirality of molecules. There are several methods in knowing the chirality of
molecules. Number one, draw the mirror image of the molecule and see if the
two molecules are the same or different. If they are different, then the molecule
is chiral. If they are the same, then it is not chiral. Number two, if the molecule
has only one chiral center, then the molecule is chiral. If the molecule has more
than one chiral center, it is most likely chiral. Lastly, If a molecule has a plane
of symmetry, then the molecule is not chiral. Aside from that the students have
also gained knowledge and has been able to differentiation conformational and
configurational stereoisomers. Configurational isomers are stereoisomers that
cannot be converted into one another by rotating the molecule around a single
bond. The rotation of the molecule around a single bond does not give its
isomer. There are two types which are geometrical isomers and optical
isomers. Conformational isomers on the other hand are stereoisomers that can
be converted into one another by rotating the molecule at a single bond. The
rotation of the molecule around a single bond can give multiple isomers. There
are four types which are eclipsed conformation, staggered conformation,
gauche conformation and anti-conformation. The study of stereochemistry is
important especially in terms of pharmaceutical studies since it tackles about
the spatial arrangement of atoms that forms the structure of molecules and how
to manipulate them which is very much needed in the making of medicinal
drugs.