Practice Problems
Practice Problems
Convert the following bond-line structures to the Newman projections as seen from the
indicated angle:
1. A 2. 3. 4.
CH3 Cl HO CH3
NH2
H
H 3C H 3C
O H C Br F H3C OH
3 B
2. (a) Consider the following cyclohexane conformational equilibrium and convert the
structures to the Newman projections as seen from the indicated angle:
A Cl CH3 B
HO
CH3 Cl
OH
A B C D
4. (a) Consider the following boat conformation for cyclohexane and convert the structure to
the Newman projection as seen from the indicated angle:
H H
H H H
H
H
HH
H H
boat conformation
CH3 OH
H 3C Cl
Cl
Br
F OH
F CH3 OH
CH3
A B C D
6. Draw a qualitative energy diagram for CH3CH2CH2CH(CH3)2, relative to the
bond between the two CH2 carbons. The Newman projections are drawn below,
using “iPr” as an abbreviation for the isopropyl CH(CH3)2 group. Put “S” (for
staggered) by any “staggered” conformation, and “E” (for eclipsed) by an eclipsed
conformation.
H 3C
CH3
Lowest energy
H 3C CH3
CH3
Lowest energy
MeO
H
O O O
O O
CH3 Cl
H
O
Cl
O
I
A B C D
Practice problems
2. Calculate the formal charges on the C, N, and O in the following compound. What is the overall
charge on this molecule?
H C N O
O
H
NH2
O
4. Indicate the hybridization of each atom, except Hs, in the following molecule. Indicate the
geometry at each carbon.
5. For each of the bonds indicated by the arrows in the following molecule, indicate the type of
bond and the type of orbitals that overlap to form it.
H H
H
H
6. Show an additional resonance structure for this anion and explain which structure contributes
more to the resonance hybrid.
O
CH3
H
8. For the following compound, explain whether or not the "unshared" electron pair on each
nitrogen is part of the conjugated π system and is involved in resonance.
N
H
O O
OH OH
O2N MeO
O O
OH OH
OMe
a) Dichloromethane h) trans-1-Bromo-2-chlorocyclobutane
b) 1-Bromo-1-chloroethane i) cis-1-Bromo-2-chloroethene
c) 2-Bromopropane j) trans-1-Bromo-2-chloroethene
d) 2-Chlorobutane k) (2S,3R)-2,3-Dibromobutane
e) cis -1,2-Dichlorocyclopropane l) (2R,3R)-2,3-Dibromobutane
f) trans-1,2-Dichlorocyclopropane m) (1R,3S)-1,3-Dimethylcyclohexane
g) trans-1-Bromo-3-chlorocyclobutane
Me Me Me Br
a) b) HO H
H H H
HO Br Br OH HO Br
Me
Me OH Me OH
c) H H d) H Me
HO Br Me Br HO Br H Br
Me Me Me Me
e) f) Cl Cl
H D Me OH HO Me
HO Br Br OH H H
H H
Me
OH OH
g) h)
Br Me Br OH OH
O O
(+)-camphor (-)-camphor
2. A pure sample of the (+)-2-bromobutane of compound C shows [a]20D = 23.1o. What
would be the observed a if a solution of the sample was made by dissolving 0.250 g in 2.0
mL of acetontirile and was then placed in a 0.5 dm cell?
3. For the following molecules, identify their stereocenters and determine the number
of stereoisomers expected.
H
O O
P N
O O O OH
HO P
HO O
N O
H
Fosfomycin Ibuprofen
Psilocybin
N
H
OH NH2
H
S O N N
N NH2 S
OH O O O
O N N O
O
OH O
O
Epivir elacestrant Darunavir
4. For the following molecules, identify their stereocenters and determine their
absolute configuration using Cahn-Ingold-Prelog Rules (R or S):
O
H OH
Br OH
CH3 NH2
Cl
A B C D
OH
O O OH OH OH H OH
NH H OH
N O O Br
O HO
O Br
HO
O
E F G H
OH
Br Br Cl Cl
Cl
Cl Br
Br OH Cl
A B C D
CH3 H OH O OH
H H HO Cl
HO
H CH3 OH CH3
Cl
H H O OH CH3
E F G
Practice problems
1. The atomic number of boron is 5. The correct electronic configuration of boron is:
A. 1s2 2s3
B. 1s2 2p3
C. 1s2 2s2 2p1
D. 2s2 2p3
E. 1s2 2s2 3s1
2. How many distinct p orbitals exist in the second electron shell, where n = 2?
Me H
N
H H
8. Which of the following are correct Lewis structures for nitric acid, HNO3?
O O O
H N O H N H N
O O O O O
A B C
H
O O
and O and O
H H
A B
H H
C C N and C C N
H H
C
12. When filling two or more orbitals of the same energy with electrons, the electrons will go into
different orbitals rather than pair up in the same orbital. ___ True ___ False
13. One or more of the atoms in the structure shown should have nonzero formal charges. Redraw
the structure and indicate any such charges.
H
P C
H
14. One or more of the atoms in the structure shown should have non zero formal charges.
Redraw the structure and indicate any such charges.
H
H B C N
H
16. The __________ tells us that each orbital can hold a maximum of 2 electrons.
A. Aufbau principle
B. Pauli exclusion principle
C. Hund's rule principle
D. Le Chatelier principle
E. Uncertainty principle
20. What kind of orbitals result when orbitals of different atoms interact?
21. What kind of molecular orbital (σ or π) results when the two atomic orbitals shown below
approach each other head to head as indicated?
23. Which of the following statements about π molecular orbitals is/are correct ?
A. They are cylindrical.
B. Most of their electron density is centered above and below the internuclear axis.
C. When two atoms are connected by a double bond, both of those bonds are pi bonds.
D. Both B and C.
E. A, B, and C.
24. The HCN bond angle in hydrogen cyanide (HCN) is __________ degrees.
27. In boron trifluoride (BF3) the boron atom is ____ hybridized and the FBF bond angle is ______
degrees.
28. In triethylamine [(CH3CH2)3N] the N atom is ____ hybridized and the geometry of the N atom is
_____.
29. Structures which differ only in rotations about a single bond are called __________.
A. Structural isomers
B. Geometric isomers
C. Conformers
D. Resonance structures
34. Which one of the molecules shown below has no net molecular dipole moment?
A. CH3Cl
B. H2C=CH2
C. CH2O
D. CH2Cl2
E. CH3OH
35. Choose the term below which best describes the geometry of acetylene (HC CH).
A. trigonal bipyramidal
B. trigonal
C. tetrahedral
D. square planar
E. linear
36. Which of the functional groups below contain a hydroxyl group as a part of their structure?
A. aldehyde
B. alcohol
C. carboxylic acid
D. amine
E. B and C
38. How many σ bonds and how many π bonds are present in the molecule shown?
CN
39. How many σ bonds and how many π bonds are present in acrylonitrile, CH2=CHCN?
40. Which of the following statements concerning the cyclic molecule shown is not true ?
A. It contains a π molecular orbital formed by the overlap of a carbon p orbital with an
oxygen p orbital.
B. It contains a σ molecular orbital formed by the overlap of two carbon sp2 orbitals.
C. It contains a σ molecular orbital formed by the overlap of two carbon sp3 orbitals.
D. It contains a π molecular orbital formed by the overlap of two carbon p orbitals.
E. It contains a σ molecular orbital formed by the overlap of a carbon p orbital with an
oxygen sp3 orbital.
41. Provide an acceptable IUPAC name for the alkane shown below.
Cl NaOH
A.
DMF
B. KCl
OTs
H 2O
C. EtOH
Br heat
D. KBr
OTs
Acetonitrle
E. H 2O
I heat
2. Explain the formation of the products from the following reactions:
Br
H2O, heat
A.
CH3 H3C OH
CH3OH, heat
B. OCH3
Br
3. Below are sets of starting materials (electrophiles) and solvents for hypothetical
nucleophilic substitution reactions. Determine whether each reaction would likely
follow an SN1 or SN2 mechanism:
4. For each reaction draw the expected major organic product(s). The products must
be drawn as line-angle structures. Clearly indicate the appropriate stereochemistry
using hashed and wedged bonds where necessary. If the product(s) is/are formed as
more than one diastereomer, draw all diastereomers formed. If the product(s) is/are
formed as a racemate (racemic mixture) draw only one enantiomer and write the
word “racemic” beneath/beside it.
5. Rank each set of electrophiles in increasing order of reactivity (least to most). The
electrophilic atoms to consider are highlighted.
6. Rank each set of nucleophiles in increasing order of reactivity (least to most). The
nucleophilic atoms to consider are highlighted.
Practice problems
OH
OH
H
CH3
C C C
H CO2H
CH2OH
HO2C
H CO2H
Cl
Me
Me
O
6. Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Me
OH Me
HO
Me
OH
Cl
10. Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate three
dimensional stereochemical detail properly.
11. How many asymmetric carbons are present in the compound below?
Me
12. How many asymmetric carbons are present in the compound below?
OH
O
HO
HO OH
OH