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Chem 23.1
Inorganic Analytical Chemistry Laboratory

Isomerism and Stereochemistry

Asparin, Jade Frances B.
College of Science, University of the Philippines-Cebu, Philippines
Contact number: +639954619301 Email address: jbasparin@up.edu.ph

Worksheet Answers

A. Isomerism

1. Methane, CH4
a. Is there any difference between the way that these configurations look? Can the four atoms be
considered equivalent?
 No there is no difference between the ways that the configurations look because only in the
presence of a lone pair does a bond distort. In the case of methane, all H atoms have equal
electronegativity leaving behind no lone pairs. Thus the electrons are shared with equal
density of which we call the sp3 hybridization. This makes the H atoms equivalent.
b. Tilt the model such that only two H atoms are in contact with the desk and imagine pressing the
model flat onto the desktop. What would the 2-D representation of this look like? Draw the
corresponding projection.
 Refer to the worksheet for the projection

2. Chloromethane or methyl chloride, CH3Cl

a. Grasp the atom representing Cl and tilt it to the right, keeping two H’s on the desk. Draw the resulting
2-D projection when flattened or viewed on top of the desk
 Refer to the worksheet for the projection
b. Does the structure of CH3Cl change between these projections?
 No, the structure does not change because it represents the same molecule.

3. Dichloromethane, CH2Cl2
a. Are the projections below (i) representations of the same compound, or (ii) different isomers of
CH2Cl2? Why?
 The projections are only representations of the same compound and not isomers. This is
because there has been no change in branching or in atom arrangement which are
characteristics of isomers.
4. Ethane, C2H6.
a. Write the structural formula for ethane.
 Refer to the worksheet
b. Are all six hydrogens in ethane equivalent? Why or why not?
  Yes, all the six hydrogens of ethane are equivalent. This is because no matter what way the
compound is named, it will still be the same (ethane). Moreover, each individual hydrogen
atom is in an identical environment (attached to a carbon atom that is linked to 2 other
hydrogens and one methyl group).
For letters c and d, kindly refer to the worksheet.

e. Twist and turn your model. Draw two different Newman projections of chloroethane. Do these
projections represent (i) different isomers or (ii) conformers of the same compound? Why?
 The two projections are conformers of the same molecule. As seen in the projection, the
first is eclipsed while the other is staggered.
f. Are all the hydrogens in chloroethane equivalent? If not, which one/s are equivalent to each other?
 Yes, all hydrogens are equivalent because no matter what way the molecule is named, it
will still be the same.

5. Dichloroethane, C2H4Cl2
a. Draw and compare these two structures. Are these (i) isomers or (ii) the same compound? Why or
why not? Assign IUPAC names to the two structures.
 The two structures appear to be isomers--specifically stereoisomers--since they differ in
atom arrangement. The first structure has both chlorine atoms in carbon 1, while the second
structure is a superimposable mirror-image (diastereomers).
b. In each structure, which hydrogens are equivalent to each other?
 For both the first and second structures, the hydrogens will still be equivalent either way.
This is because the naming holds true no matter which side of the chain will be chosen.

6. Isomers of C2H6O (dimethyl ether and ethanol)

a. Manipulate each model by twisting or turning. Can either be turned into the other?
 It cannot be turned into the other by mere twisting or turning because the position of their
oxygen atoms are different.
b. Label and compare the equivalent hydrogens present in each isomer.
 Refer to the worksheet

7. Butane, C4H10
a. Are these (i) isomers or (ii) different orientations of the same compound?
 These are basically just different orientations of the same compound. This is because there
has been no significant change in connectivity or in atom arrangement which can qualify it
to be an isomer.

c. Based on this, how many distinct chlorobutane (C4H9Cl) isomers are possible? Draw their
structures and assign IUPAC names.
 There are only two distinct isomers which are 1-chlorobutane and 2-chlorobutane. (Refer
to the worksheet for the structures)
d. Is the resulting structure an isomer or the same compound? If yes, draw its structure and give its
IUPAC name.
 Yes, it is an isomer of the given compound which is 2-methylpropane. (Refer to the
worksheet for the structure)
e. Which hydrogens are equivalent to each other in the reconstructed second butane model? Based
on this, how many distinct chlorobutane (C4H9Cl) isomers are possible? Draw their structures and
assign IUPAC names. Compare your answers with those obtained from (c).
  All hydrogens are equivalent to each other in the reconstructed second butane model
because if we replace any of the nine CH3 atoms with a Cl, we will get the same compound:
1-chloro-2-methylpropane. So the nine CH3 atoms form one set of equivalent H atoms.
Consequently, if we replace the H atom on C-2, we’ll get a different compound: 2-chloro-
2-methylpropane. Therefore, the lone H atom forms a second set of 1 hydrogen atom by
itself.
 There are 2 distinct chlorobutane isomers possible: 1-chloro-2-methylpropane and 2-
chloro-2-methylpropane. (Refer to the worksheet for the structures)
 From the answers obtained in c, we observed that the number of carbon, hydrogen and
chlorine atoms are similar. The only difference is the position of chlorine and the nature of
the chain (branched or chain). From this observation, we inferred that the 4 structures from
answers c and e are constitutional isomers.

B. Stereochemistry

2. Stereocenter with four different substituents: red, white, blue, and green
a. Does this model have a plane of symmetry? Molecules without a plane of symmetry are
said to be chiral; otherwise they are achiral.
 No, there is no plane of symmetry; hence, it is chiral.
b. Construct the mirror image of the original model. Is it chiral? Try to superimpose the second
model onto the first (i.e., the atoms fall exactly one on top of the other). Are these mirror images
superimposable? Enantiomers are two molecules that are non-superimposable mirror images of
each other.
 Yes, it is chiral and the images cannot be superimposable. Thus, both models are
enantiomers.
c. In the first model (a), replace the blue atom with a second green atom. Is this new model chiral or
achiral? Why? If it has a plane of symmetry, what are the left and right halves of the cutting plane?
 Given the replacement of the blue atom with another green atom, there appears to be a
plane of symmetry because of the two identical substituents. This, then, makes the model
achiral. If we cut it in half, the left half of the cutting plane will have a green atom and the
other half will also have a green atom.
d. Construct the mirror image of the model in (c). Are the two models (c) and (d) enantiomers or
just identical molecules? Why?
 Both are just identical molecules because there is a line of symmetry which makes the
molecule achiral. However, it is not an enantiomer because the molecules can be
superimposed over the over.
e. Reconstruct the original models of (a) and (b). Draw and compare both the dashed-line-wedge
and Fischer projections of the two enantiomers (a) and (b).
 Refer to the worksheet for the figures.
f. If you have any Fischer projection and rotate it by 180o, is the resulting projection representative
of the same molecule?
 Rotation of the Fischer projection by 180º in either direction without lifting it off the plane
of the paper does not change the absolute configuration at the chiral center. Since it is only
the orientation that has changed, it is still the same molecule. The assumption holds true.
g. Go back to the original model in (a) and interchange the position of the red and green atoms.
Draw the Fischer projection. Does this exchange give you the enantiomer? Now interchange the
 blue and white atoms. Does this return you to the original model? What generalizations can be
made regarding Fischer projections?
 Yes, it will result in an enantiomer because now it is a mirror image and non-
superimposable. Yes, it will return to the original model. (Refer to the worksheet for the
projection)
 With this, a molecule that is turned 180 degrees on the sample plane will still result as the same
structure. If it is mirrored, however, it will produce an enantiomer.

3. Tartaric acid
a. Is there a plane of symmetry in tartaric acid? Is the molecule chiral or achiral?
 Tartaric acid lacks a plane of symmetry therefore it is chiral.
b. Are the two models enantiomers or identical molecules? Why?
 The two models are not enantiomers. They are just identical or more specifically
called meso compounds.
c. Does this new model have a plane of symmetry? Is it chiral or achiral?
 Since there is no plane of symmetry, it is chiral.
d. Does this new model have a plane of symmetry? Is it chiral or achiral?
 It also has no plane of symmetry. Thus, it is chiral.
e. Diastereomers are stereoisomers that are not related as mirror images. Compare models (a), (b),
(c), and (d). Which pairs are enantiomers? Which pairs are diastereomers? Which pairs are
identical (these are called meso compounds)?
 Enantiomers: A & B, C & D
 Diastereomers: A & C, B & D
 Mesocompounds: A & B, C & D
f. Draw and compare the Fischer projections of (a), (b), (c), and (d). What conclusions
can be drawn?
 Enantiomers are chiral and non-superimposable molecules, whereas
diastereomers can be achiral and can be superimposable while still being
isomers. As for mesocompounds, these are compounds with a plane of
symmetry.