Chapter 5

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Section: 5.1

1. Which of the following represent cis isomers?

A. B. C.

D. E. F.

G. H. I.
Answer: b, f, g, h

For more examples of this type of problem, see Skillbuilder

5.1.
Section: 5.1

1. Which of the following represent cis isomers?

A. B. C.

D. E. F.

G. H. I.

a. a, b, f, g
b. a, f, g, h
c. b, c, g, h
d. b, f, g, h
e. c, e, h, i
Answer : d
Section: 5.2

2. Identify all the chirality centers in the following molecules….

Answer: 4, 7, 8

Tetrahedral carbons with 4 different groups are chirality

centers. For more examples of this type of problem, see
Skillbuilder 5.2.
Section: 5.2

2. Identify all the chirality centers in the following molecules….

a. 4
b. 7
c. 8
d. 4, 8
e. 4, 7, 8
Answer is: e
Section: 5.3

3. Which of the following is the highest priority in the Cahn-Ingold-

Prelog system of prioritizing groups for R/S nomenclature?

 a. Propyl group

 b. Methyl group
 c. Bromine
 d. Chlorine
Answer: c

Priority is determined by atomic number, Br = 35, Cl = 17,

C = 6, C = 6. Therefore, Br has the highest priority. For
more examples of this type of problem, see Skillbuilder 5.4.
Section: 5.3

4. Using the priorities assigned to carbon 2, what is the

stereochemical designation of carbon 2?

 a. R
 b. S
 c. neither
Answer: b

Orient the molecule with the methyl facing away from you,
the bromine is #1 then you go counterclockwise to the
chlorine and then continue counterclockwise to the propyl.
Therefore, the designation is S. For more examples of this
type of problem, see Skillbuilder 5.4.
Section: 5.3

5. What is the stereochemical designation of carbon 2?

 a. R

 b. S

 c. neither
Answer: b

Bromine is priority #1, propyl is #2 and methyl is #3.

Hydrogen, the #4 priority group, is already facing away from
you. Starting at bromine you go counterclockwise to get to the
propyl. Therefore, the designation is S. For more examples of
this type of problem, see Skillbuilder 5.4.
Section 5.3 b. S

 c. neither

6. What is the stereochemical designation of carbon 2?

 a. R

b. S

 c. neither
Answer: a

Bromine is priority #1, propyl is #2 and methyl is #3. Hydrogen,

the # 4 priority group, is facing towards you. When the #4 group
is facing towards you, start at #1 priority and determine if you
go counterclockwise or clockwise just like you would normally.
Starting at bromine you go counterclockwise to get to the
propyl. Therefore, the designation would normally be S. Since
the #4 group is facing you, whatever orientation you get (which
is S in this case), change it to the other one (which would be
R). Therefore, this is R. Bottom line: when #4 group faces you,
figure out R/S as usual and then change it to the opposite
orientation. For more examples of this type of problem, see
Skillbuilder 5.4.
Section: 5.3

7. What is the stereochemical designation of the following

molecule?

 a. R

 b. S

 c. neither
Answer: b

All four attached groups are carbons, which have the same
priority. When you have groups with the same atomic #,
especially carbon, you proceed to the other attached groups
to the carbon. In this case we have a CH3, CH2, CH2, CH.
This means CH is highest priority and CH3 is lowest priority.
The other two are CH2CH3 and CH2CH2CH3. If you look at
each one's second carbon you are comparing a CH3 to a
CH2, CH2 has less hydrogen so is higher priority. This means
CH2CH3 is third in priority and CH2CH2CH3 is second in
priority. Going from the highest priority, you move clockwise.
But since the lowest priority if facing you, the correct
designation is S. For more examples of this type of problem,
see Skillbuilder 5.4.
Section: 5.3

8. What is the stereochemical designation of the following

molecule?

 a. R

 b. S

 c. neither
Answer: c

In assigning priority, the OH is #1 and the hydrogen is #4. But

the carbon clockwise from the “stereocenter” is CH double
bonded to a CH to a C with two methyls. The carbon
counterclockwise from the “stereocenter” is CH double bonded
to CH to a C with two methyls. In other words, you cannot
decide which side has priority. In addition, this molecule has a
plane of symmetry going through the alcohol carbon,
consistent with this position being achiral. Therefore, the
designation is neither R nor S. For more examples of this type
of problem, see Skillbuilder 5.4.
Section: 5.4

9. If a sample of the pure R enantiomer of a molecule has a

specific rotation of – 40° and your mixture of that molecule has an
observed optical rotation of + 22°, what is the % ee of your
sample?

 a. 55 % ee R

 b. 55 % ee S

 c. 18 % ee R

 d. .55 % ee R

 e. none of the

above
Answer: b

% ee = (observed/specific) × 100% ee = (22/40) × 100; 0.55 ×

100 = 55 %. Since the pure R rotates the polarized light
counterclockwise or levorotatory (which is determined by the
rotation being negative) and your observed rotation is positive,
that means your sample has more S than R since S is positive
in this case. For more examples of this type of problem, see
Skillbuilder 5.5 and 5.6.
Section 5.4

10. If a sample is 50 % ee of R stereoisomer, what is the % R in

the mixture?

 a. 50

 b. 100

 c. 25

 d. 75
Answer: d

If a sample is 50 % ee R, that means 50 % is pure R. The

other 50 % is 1/2 R and 1/2 S. 1/2 of 50 is 25 %. Therefore,
the mixture is 75 % R(50 + 1/2(50)) and 25 %S (1/2 (50)). For
more examples of this type of problem, see Skillbuilder 5.6.
Section 5.4

11. If a chemical reaction produces a mixture of 80% R and 20 %

S, what is the % ee?

 a. 80

 b. 60

 c. 20

 d. 4
Answer: b

% ee = % R – % S or 80 – 20 = 60 % ee. For more

examples of this type of problem, see Skillbuilder 5.6.
Section 5.4

12. If a sample of the pure R enantiomer of a molecule has a

specific rotation of – 40° what is the specific rotation of pure S?

 a. –60°

 b. +60°

 c. –40°

 d. +40°

 e. cannot be
determined
Answer: d

Whatever the specific rotation is for one isomer, the other

isomer will be the same value with the opposite sign.
Therefore, –40 is R so +40 is S. For more examples of this
type of problem, see Skillbuilder 5.5.
Section: 5.4

13. If the specific rotation of (R)-2-methylhexan-2-ol is –35°, what

is the specific rotation of (S)-hexan-2-ol?

 a. –35°

 b. +35°

 c. it is negative but value

cannot be determined

 d. it is positive but value

cannot be determined

 e. it cannot be determined

Answer: e

If the R isomer of one molecule is negative, the S isomer of

that same molecule will be positive. But the S isomer of a
different molecule could be either negative or positive. For
more examples of this type of problem, see Skillbuilder 5.5.
Section 5.4

14. If a sample of the pure R enantiomer of a molecule has a

specific rotation of – 40° and your mixture of that molecule has
an 82% ee S, what is the observed specific rotation of your
sample?

 a. +40°

 b. +8.2°

 c. +32.8°

 d. –48.7°

 e. cannot be
determined
Answer: c

% ee = (observed/specific) × 100. 82 = (X/40) × 100; 82 =

(100 X)/40; 82 × 40 = 100 X; 3280 = 100 X; X = 3280/100 =
32.8. Since the pure R rotates the polarized light
counterclockwise or levorotatory (which is determined by the
rotation being negative) and your mixture is predominately S,
the observed rotation will be positive. For more examples of
this type of problem, see Skillbuilder 5.5.
Section: 5.5

15. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: b

There is one stereocenter, so disastereomers are

eliminated. The molecules have the same formula and
connectivity so different molecules and constitutional
isomers are eliminated. The two molecules are
nonsuperposable mirror images of each other; therefore,
they are enantiomers. Additionally, the first molecule is R
and the second is S. This also makes them enantiomers of
each other. For more examples of this type of problem, see
Skillbuilder 5.7.
Section: 5.5

16. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: a

There is one stereocenter, so disastereomers are

eliminated. The molecules have the same formula and
connectivity so different molecules and constitutional
isomers are eliminated. The two molecules are
superposable mirror images of each other; therefore, they
are the same molecules. Additionally, the first molecule is R
and the second is R. This also makes them the same
molecule. For more examples of this type of problem, see
Skillbuilder 5.7.
Section 5.5

17. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: b

There are two stereocenters, so disastereomers are not

eliminated. The molecules have the same formula and
connectivity so different molecules and constitutional
isomers are eliminated. The two molecules are
nonsuperposable mirror images of each other; therefore,
disatereomers and the same molecules are eliminated.
Additionally, the first molecule is (2R, 3S) and the second is
(2S, 3R). This also makes them enantiomers of each other.
If two molecules have exactly opposite designations they
are enantiomers, i.e. R,R,R is the enantiomer of S,S,S and
so forth. For more examples of this type of problem, see
Skillbuilder 5.7.
Section: 5.5

18. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: e

The two molecules have different connectivities but the same

molecular formula. The first molecule has a methyl on carbon
4, the second molecule has a methyl on carbon 3. These are
constitutional isomers. For more examples of this type of
problem, see Skillbuilder 5.7.
Section: 5.5

19. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: c

There are two stereocenters, so disastereomers are not

eliminated. The molecules have the same formula and
connectivity so different molecules and constitutional
isomers are eliminated. The two molecules are not
mirror images of each other and not superposable;
therefore, enantiomers and the same molecules are
eliminated. Additionally, the first molecule is (2R, 3S)
and the second is (2R, 3R). This also makes them
disatereomers of each other. If two molecules do not
have exactly opposite designations they are
disatereomers, i.e. R,R,R is the diastereomer of S,R,R
and of R,R,S and of R,S,R and so forth. For more
examples of this type of problem, see Skillbuilder 5.7.
Section 5.5

20. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: d

The two molecules have different molecular formulas. The

first molecule has 9 total carbons, the second molecule
has 10 total carbons. These are different molecules. For
more examples of this type of problem, see Skillbuilder
5.7.
Section: 5.6

21. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: a

Both drawings are of cis-1,3-dimethylhexane, which

has a plane of symmetry. Therefore, they are the same
molecule. For more examples of this type of problem,
see Skillbuilder 5.8.
Section: 5.6

22. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional
isomers
Answer: b

Both drawings are of trans-1,3-dimethylhexane,

which does not have a plane of symmetry. Therefore,
they can be the same or enantiomers. Since they are
nonsuperposable mirror images of each other, they
are enantiomers. For more examples of this type of
problem, see Skillbuilder 5.8.
Section: 5.6

23. Indicate the relationship of the pair of molecules shown.

 a. same molecules

 b. enantiomers

 c. diastereomers

 d. different molecules

 e. constitutional isomers

Answer: c

One drawing represents trans-1,3-dimethylhexane and

the other represents cis-1,3-dimethylhexane. Since they
represent the same connectivity and one is cis and the
other is trans, they are diastereomers of each other.
Cis/trans pairs are always diastereomers of each other
(as long as they have the same connectivity). For more
examples of this type of problem, see Skillbuilder 5.8.
Section: 5.7

24. What is the stereochemical designation of the indicated

chirality center?

 a. R

 b. S

 c. neither
Answer: a

For the Fischer projection, convert one of the

horizontal lines to a wedge and one of the vertical
lines to a dash. Assign priority and determine R or S.
For more examples of this type of problem, see
Skillbuilder 5.9.