Names: Balo, Marielle Date Submitted: 31 March 2017

Deseo, Maria Rogemae

Gerolaga, Winston Jake
Group: 4

EXPERIMENT NO. 6
STEREOCHEMISTRY

I. Introduction

Stereochemistry is concerned with the shapes of molecules and how the

differences in shapes can affect the properties and reactions of compounds. Subtle
differences in molecular shape have far-reaching consequences and it is probably the
field of molecular biology that a full awareness of molecular shapes has emerged.
Knowledge of the molecular shapes of vital compounds such as sugars, amino acids,
and proteins is essential in understanding their reactions and properties. 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 persuade you to think in three dimensions.

II. Chirality, enantiomerism, diastereomerism and optical activity.

Objects which are IDENTICAL are SUPERIMPOSABLE that is, when we

imagine the two objects are used together, all the corresponding parts match exactly.
Thus, a sphere is superimposable on another sphere of the same diameter. A sphere,
however, is not superimposable on a cube nor on a sphere of a different diameter.

1. Determine whether the following pairs of objects are superimposable or not

superimposable with each other.
a. Two forks
Answer: SUPERIMPOSABLE.
b. Your left hand and your right hand
Answer: NOT SUPERIMPOSABLE.
2. Yes or No. View your right hand in front of the mirror.
a. Is the reflection of your right hand superimposable on your left hand?
Answer: NO.
b. Is your right hand the mirror image of your left hand?
Answer: NO.

3. Using a mirror, decide whether the following objects are superimposable or not
superimposable on their mirror images.
a. A fork
Answer: SUPERIMPOSABLE.
b. A pentagon
Answer: SUPERIMPOSABLE.
c. Your left hand
Answer: NOT SUPERIMPOSABLE.

A PLANE OF SYMMETRY is an imaginary plane or sheet that divides the

objects so that one half is exactly a reflection of the other half.

4. Yes or No. Tell whether the following objects contain at least one plane of symmetry.
a. A sphere
Answer: YES.
b. A regular tetrahedron
Answer: YES.
c. A shoe
Answer: NO.

5. Determine whether the objects in No. 4 are superimposable or not superimposable

on their mirror images.
a. A sphere
Answer: SUPERIMPOSABLE.
b. A regular tetrahedron
Answer: SUPERIMPOSABLE.
 c. A shoe
Answer: SUPERIMPOSABLE.

6. Describe the relationship between the presence of a plane of symmetry in an object

and the objects superimposability on its mirror image in your own words.
Answer: If there is a presence of a plane of symmetry in a molecule, then the
molecule will be superimposable on its mirror image.

Objects which are not superimposable on their mirror images are

CHIRAL objects, while those which are superimposable on their mirror images
are ACHIRAL.

7. Look for the model of CH4. Is it chiral or achiral? Why?

Answer: Methane (CH4) is achiral since there is a

plane of symmetry and it is superimposable on its
mirror image.

8. Look for the model of CBrFClH. Is it chiral or achiral? Why?

Answer: CBrFClH is chiral since the mirror image of the

molecule is not superimposable.

Non-superimposable mirror images are called ENANTIOMERS.

9.
a. Are enantiomers chiral?
Answer: YES.
 b. Do enantiomers have the same formula?
Answer: YES.
c. Does one structural formula represent both members of a pair of
enantiomers?
Answer: NO.

10. Are enantiomers stereoisomers?

Answer: Yes because their only difference is their three-dimensional
arrangement.

One of the most important property of chiral molecules is their effect on plane
polarized light. Both enantiomers rotate the plane of polarized light. Substances with
this property are said to be optically active. Chiral substances containing molecules
which are not superimposable on their mirror images are optically active. Enantiomers
are also known as optical isomers.

11. Determine whether each of the following are optically active or optically inactive.
a. CH3CH(NH2)COOH
Answer: OPTICALLY ACTIVE.
b. CH3CH2CHClCH3
Answer: OPTICALLY ACTIVE.
c. CH3CH2CH2CH3
Answer: OPTICALLY INACTIVE.

The rotation of the plane polarized light is used to observe experimentally

one of the main differences between a pair of enantiomers. One enantiomer rotates
plane polarized light clockwise (as seen by the observer), the other enantiomer,
counterclockwise by the same amount. Conventions used to indicate the direction of
rotation of the plane of polarization are:

Clockwise (+): dextrorotatory, d

Counter-clockwise ( - ): levorotatory, l
12. Which enantiomer of alanine rotates the plane-polarized light clockwise?
Answer: (+)-alanine

13. Which of the following aqueous solutions are likely to be optically inactive?
a. A solution of ethanol, CH3CH2OH
Answer: OPTICALLY ACTIVE.
b. A solution of (+)-alanine
Answer: OPTICALLY ACTIVE.
c. A solution of (-)-alanine
Answer: OPTICALLY ACTIVE.
d. A solution containing equimolar quantities of (+)-alanine and (-)-alanine
Answer: OPTICALLY INACTIVE.

A mixture containing equimolar quantities of a pair of enantiomers is called a

RACEMIC MIXTURE.

14. How is the racemic mixture of alanine represented?

Answer: ()-alanine

15. Examine the models for the presence of a plane symmetry. Which of them has at least
one plane of symmetry?

(a) (b) (c) (d)

Answer: A and B.

16. Which are superimposable on their mirror image?

Answer: A, B, and C.
 17. Which model represents a chiral molecule?
Answer: D only.

18. How many different atoms of groups of atoms must be attached to the central carbon
atom in order to confer chirality to the molecule?
Answer: There should be four different types of atoms or groups of atoms
attached to the central atom in order to confer the chirality of the
molecule.

Consider the following structural formulas for items 19 and 20.

(a) (b)

19. Which is a chiral molecule?

Answer: A only.

20. Which can exist as pair of enantiomers? Draw the pair of enantiomers.
Answer: A only.

HOOC CH3

HO

Now, we will consider molecules with more than one chiral center. Consider 2,3-
dihydroxybutanoic acid.
 The flying-wedge representation of 2,3-dihydroxybutanoic acid is shown below.

MIRROR
IMAGE

(I) (II)

21. No question.
22.
a. Draw the flying wedge representation of its mirror image (II).

(I) (II)

b. Are I and II chiral?

Answer: NO.

A compound which contains two different chiral centers can exist as four optically
inactive stereoisomers. The flying-wedge representations of the four stereoisomeric 2,3-
dihydroxybutanoic acid are given below.
 Some are related as enantiomers while others, called DIASTEREOISOMERS are
not related as mirror images at all.

23. What is the relationship between

a. I and II
Answer: ENANTIOMERS.
b. III and IV
Answer: ENANTIOMERS.
c. I and IV
Answer: DIASTEREOMERS.
d. II and IV
Answer: DIASTEREOMERS.

24. What is the relationship between

a. I and III
Answer: DIASTEREOMERS.
b. II and III
Answer: DIASTEREOMERS.

CONFORMATIONS. Atoms within the molecules can vibrate and are free to rotate
about the single bond. This rotation may result in the atom taking different positions
relative to the rest of the molecule. Molecular structures that are interconvertible by simple
bond rotations are called conformations.

OPEN CHAIN COMPOUNDS

25. Look for the model of ethane. Rotate the C C single bond.
a. Is there a change in the relative positions of the different atoms as the C
C bond is rotated?
Answer: YES.
b. Does the ethane molecule have more than one conformation?
Answer: YES.
 Ethane can adopt an infinite number of conformations but the two extreme
conformations are eclipsed and staggered.

NEWMAN PROJECTION

Eclipsed Staggered

SAWHORSE PROJECTION

Eclipsed Staggered

26. In which extreme conformation are the hydrogens farthest apart from each other?
Answer: Staggered conformation.

27. Draw the Newman and Sawhorse representation of ethane with the highest potential
energy.
 28. Draw the Newman and Sawhorse representation of ethane with the lowest potential
energy.

29. Which is the preferred conformation of ethane?

Answer: Staggered conformation.

30. Look at the model of chloroethane.

a. Do all chloroethane molecules spend all of their time in this preferred
conformation?
Answer: YES.
b. What is the preferred conformation called?
Answer: Staggered conformation.

RING COMPOUNDS

31. Look at the model of cyclohexane. Rotate the carbon atoms and examine the different
conformations.
a. Are there any conformations in which all carbon atoms of the ring are in
one plane?
Answer: NO.

The two extreme conformations of cyclohexane are referred to as chair and boat.
 Put your model carefully in the chair conformation. Look at the relative positions of
the hydrogen atoms along the axes of C2 C3 and C5 C6. Hold carbons 2, 3, 5, and 6 firmly in
one hand, then without moving carbon 1, flip carbon 4 up (or down) without breaking any bond.
Again look at the relative positions of the hydrogens along the C2 C3 and C5 C6 bonds.

32. Does flipping of carbon 4 result in a change in conformation?

Answer: YES.

33. In which conformations are the hydrogens farthest apart?

Answer: Chair conformation.

34. Which is the preferred conformation?

Answer: Chair conformation.

Compare your models with the Newman projections below by looking through the
C2 C3 and C5 C6 bonds at the same time.

35. Which is the eclipsed conformation?

Answer: II

36. Which is the staggered conformation?

Answer: I

In the chair conformation, there are two conformations of the hydrogen atoms.
Bonds that are oriented vertically are called axial bonds while the rest is known as equatorial
bonds.
37. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon
4. What is the resulting conformation?
Answer: Chair projection.

38. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon 1. What is now the
resulting conformation?
Answer: Boat conformation.

39. Did you break any bonds?

Answer: NO.

40. What is the orientation of the marked bonds now?

Answer: Equatorial bond.

41. Make a sketch of the final conformation showing the marked bonds.

Now with the equatorial bonds marked, reverse the process and rotate the bonds
to reform the chair conformation with the axial bonds marked. This overall process of one
chair conformation changing to another chair conformation is called RING INVERSION.

42. Represent the process using the symbol to indicate that the to chair conformations
are in dynamic equilibrium.
43. Construct a model of methylcyclohexane with the methyl attached axially. Make the
ring undergo inversion and complete the following.

(a) (b)

44.
a. In which chair conformation (a or b) is the methyl group farthest from the
neighboring hydrogen atom?
Answer: Conformation A.
b. In which chair conformation (a or b) does the methyl group have greater
room?
Answer: Conformation B.
c. Which is the preferred conformation?
Answer: Conformation A.

45. Make a general statement about the preferred conformation of monosubstituted

cyclohexanes.

A substituent on the cyclohexane ring can occupy the axial or equatorial position.
Interconversion between cyclohexane with methyl in the equatorial position and
cyclohexane with methyl in the axial position takes place via a ring flip. The conformation
where methyl is in the equatorial position is more stable by around 1.7 kcal/mol therefore,
it is the most preferred conformation of a monosubtituted cyclohexane.