Escolar Documentos
Profissional Documentos
Cultura Documentos
EXPERIMENT NO. 6
STEREOCHEMISTRY
I. Introduction
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.
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.
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.
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.
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.
15. Examine the models for the presence of a plane symmetry. Which of them has at least
one plane of symmetry?
Answer: A and B.
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.
(a) (b)
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)
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.
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.
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.
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.
Compare your models with the Newman projections below by looking through the
C2 C3 and C5 C6 bonds at the same time.
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.
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.
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.