CH203 Fall 2014 Practice Exam 1

1) The rotational barrier in ethane is 12.6 kJ/mol, while in trifluoroethane is has been shown to
be 14.4 kJ/mol.

What is the structure of 1,1,1-trifluoroethane?




Draw an energy diagram illustrating energy vs. rotamer for trifluoroethane. Draw the
conformations for each energy minimum and transition state.




























What do you think causes this increase in energy for the rotation about the C-C bond in 1,1,1-
trifluoroethane compare to ethane?

2) Draw the structures of the following compounds

Acetic Acid



Acetone




trans-1-Amino-4-t-butylcyclohexane
(Draw a. a planar structure with stereochemical representation of substituents, and b. the most
stable conformation.)










(S)-3-Bromocyclohexanone
(Draw a. a planar structure with stereochemical representation of substituents, and b. the most
stable conformation.)










(2R,3R)-butane-2,3-diol


3) Tocetrapib (1) is a cholesterol-controlling drug used in combination with Lipitor to increase
HDLs.






How many chiral centers are in tocetrapib (1)? Label each as R or S on the structure of 1 above.




How many stereoisomers exist for this compound?


Two carbamate groups exist in 1. Draw all possible resonance structures of the carbamate group
and rank them in order of importance (starting with the carbamate as drawn)




N Et
N
OEt O
F
3
C
CF
3
O
MeO
CF
3
1

4) What is the ground-state electronic configuration of a fluorine atom (fluorine: atomic number
9)?
a. 1s
1
2s
1
2p
7

b. 1s
2
2s
2
2p
5

c. 1s
2
2s
2
2p
6

d. 1s
0
2s
2
2p
7




5) What is the ground-state electronic configuration of a fluoride anion (fluorine: atomic number
9)?
a. 1s
2
2s
2
2p
2

b. 1s
2
2s
2
2p
5

c. 1s
2
2s
2
2p
6

d. 1s
2
2s
2
2p
7



6) Which of the following is trigonal planar?
a. boron trifluoride, BF
3

b. methyl anion, CH
3
!

c. methane, CH
4

d. ammonia, NH
3


7) Which of the following statements is not true regarding resonance structures?
a. All resonance structures must have the same number of electrons
b. Each atom in all of the resonance structures must have a complete shell of valence
electrons
c. All resonance structures must have the same arrangement of atoms
d. All resonance structures must be valid Lewis structures



8) Which of the following statements is not true regarding resonance structures?
a. Each resonance structure is in rapid equilibrium with all of the other structures
b. The resonance structures may have different energies
c. All resonance structures must have the same arrangement of atoms
d. All resonance structures must have the same number of electrons

9) Which of the following is a primary (1) alcohol?



a. 1
b. 2
c. 3
d. 4

10) Which of the following is a secondary (2) amine?



a. 1
b. 2
c. 3
d. 4

11) Which of the following shows curved arrows that correctly accounts for the differences
between the two structures?



a. 1
b. 2
c. 3
d. 4


12) What is the IUPAC name of the following compound?



a. 3-propylpentane
b. 1,1-diethylpropane
c. 3-ethylhexane
d. isooctane

ANS: C

13) What is the IUPAC name of the following compound?



a. 2-ethyl-4-methylpentane
b. 2,4-dimethylhexane
c. 3,5-dimethylhexane
d. 1,1,3-trimethylpentane

14) What is the IUPAC name of the following compound?



a. 2,4-dimethyl-3-isopropyl-pentane
b. 3-isopropyl-1,5-dimethylpentane
c. 3-isopropyl-2,4-dimethylpentane
d. triisopropylmethane


15) What is the IUPAC name of the following compound?



a. 1-isopropyl-4,6-dimethylcyclohexane
b. 1-isopropyl-2,4-dimethylcyclohexane
c. 4-isopropyl-1,3-dimethylcyclohexane
d. 4-isopropyl-1,5-dimethylcyclohexane

16) What is the approximate dihedral angle between the two chlorine atoms in cis-1,2-
dichlorocyclohexane?
a. 0
b. 60
c. 120
d. 180

17) Which of the following cycloalkanes has the largest heat of combustion per carbon atom?
a. cyclopropane
b. cyclopentane
c. cyclohexane
d. cycloheptane

18) What is the IUPAC name of the following compound? Ignore chirality.


19)How many hydrogen atoms are there in decane?

20) Which of the following is the definition of a pair of enantiomers?
a. A pair of structures that are superposable mirror images of one another
b. A pair of stereoisomers that are non-superposable mirror images of one another
c. A pair of stereoisomers that are not mirror images of one another
d. A pair of stereoisomers that have equal specific rotations



21) Which of the following is the definition of a pair of diastereomers?
a. A pair of structures that are superposable mirror images of one another
b. A pair of stereoisomers that are non-superposable mirror images of one another
c. A pair of stereoisomers that are not mirror images of one another
d. A pair of stereoisomers that have equal specific rotations

22) Which of the following is the definition of a meso compound?
a. A molecule with stereocenter centers which is chiral
b. A molecule with stereocenter centers which is not chiral
c. A diastereomer with no stereocenter centers
d. A chiral compound with more than one stereocenter center

23) Which of the following have the S configuration?



a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3



24) Which of the following have the R configuration?



a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3

25) How much of the R enantiomer is present in 10 g of a mixture which has an enantiomeric
excess of 20% of the S isomer?
a. 1 g
b. 2 g
c. 4 g
d. 6 g

26) Which of the following structures has a center of symmetry (i.e., center of inversion)?



a. 1
b. 2
c. 3
d. 4


27) Which of the following structures have a plane of symmetry?



a. only 1 and 2
b. only 2 and 4
c. only 3 and 4
d. 1, 2, 3 and 4

28) What is the relationship between the following pair of structures?



a. They are enantiomers
b. They are diastereomers
c. The are constitutional isomers
d. They are identical



29) What is the relationship between the following pair of structures?



a. They are enantiomers
b. They are diastereomers
c. The are constitutional isomers
d. They are identical

30) Complete the following Fischer diagram so that it represents (2R,3R)-3-bromobutan-2-ol.