1.

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

(b) Which chair conformation is more stable? Why?

3. Convert each of the following Newman projections to the corresponding bond-line
structure (use planar structures with wedged/dashed bonds for cyclohexanes):

CH3 CH3 H CH3

H CH3 H Br H H HO
Br H I H I OH Br H
I OH Br Cl

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

(b) Is this a minima or a maxima on the torsional energy profile of cyclohexane

conformations?

(c) Which is the most energetic cyclohexane conformation? Draw a Newman

projection of such conformation to justify your answer.
5. Draw right- and left-handed chair conformations for the following cyclohexanes:

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

iPr iPr iPr iPr iPr

iPr iPr
CH3 H H H 3C H CH3
H CH3 H H
H H H 3C H
H H H H H H H H H H H H
H H H H
H H CH3 CH3 H
0o 60o 120o 180o 240o 300o 360o
Relative energy

Lowest energy

0o 60o 120o 180o 240o 300o 360o

7. Draw a qualitative energy diagram for CH3CH2CH(CH3)2, relative to the C2-C3
bond. The Newman projections are drawn below.

H 3C CH3

CH3

CH3 CH3 H 3C CH3 H 3C

H 3C H 3C
CH3 H H H 3C H CH3
H CH3 H H
H H H 3C H
H CH3 H CH3 H CH3 H CH3 H CH3 H CH3
H CH3 H H
H H CH3 CH3 H
0o 60o 120o 180o 240o 300o 360o
Relative energy

Lowest energy

0o 60o 120o 180o 240o 300o 360o

8. Determine the stereochemistry of the following alkenes:

MeO
H
O O O
O O
CH3 Cl
H
O
Cl
O
I
A B C D
 Practice problems

1. Show a Lewis structure for the stable molecule CH3CN.

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

3. What functional group (or groups) is present in these compounds?

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
7. Draw two additional important resonance structures for this carbocation.

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

9. In each case, explain which compound is the stronger acid.

O O

OH OH

O2N MeO

O O

OH OH
OMe

10. Consider the following molecules and answer the questions.

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

• Which of these molecules are chiral?

• Which of these molecules contain chiral carbons? In your drawings label them with an asterisk.
• Which of these molecules can exist as enantiomeric pairs?

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
11. Indicate whether the following pairs of compounds represent the same molecule, pairs of
enantiomers, diastereomers, or unrelated molecules.

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
1. Camphor is a waxy, colourless solid with a strong aroma. It is classified as a terpenoid and
a cyclic ketone and has a specific rotation of 44 degrees. If you have a mixture of 34% (+)-
camphor and 66% (-)-camphor, what will be the observed rotation of this mixture? Assume 1
g dissolved in 1 mL; the sample cell is 1 dm long. Express your answer in a whole number.

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

(b) Draw the enantiomer of F, as well as all possible diastereomers.

5. Are the following molecules meso or chiral compounds?

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?

3. An oxygen atom has __________ valence electrons.

4. Draw a correct Lewis structure for boric acid, B(OH)3.

5. Draw a correct Lewis structure for tert-butanol, (CH3)3COH.

6. Draw a correct Lewis structure for acetonitrile, CH3CN.

7. The formal charge on nitrogen in the compound below is __________.

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

9. The formal charge on oxygen in dimethyl ether, CH3OCH3, is ________.

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
10. Which of the following choices represent(s) a pair of resonance forms?

H
O O
and O and O
H H
A B

H H
C C N and C C N
H H
C

11. Draw an acceptable line-angle formula for the molecule shown.

H H
H OH
Me H
Me H

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
15. When a molecule can best be represented as a series of resonance forms, each of these forms
always contributes to the same degree in the hybrid. ___ True ___ False

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

17. Draw a line-angle formula for (CH3)2CHCH2CH2NH2

18. In the compound sodium methoxide (NaOCH3), there is __________ bonding.

A. ionic
B. polar covalent
C. nonpolar covalent
D. a mixture of ionic and covalent
E. resonance stabilized

19. A carbon-hydrogen bond in ethane (CH3CH3) is best described as __________.

A. highly polar
B. essentially non-polar
C. ionic
D. a multiple bond
E. resonance stabilized

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?

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
22. What kind of molecular orbital (σ or π) results when the two atomic orbitals shown below
approach each other sideways 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.

25. The HCH bond angle in propane is __________ degrees.

26. The CCO bond angle in acetone (CH3COCH3) 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

30. What is the hybridization of the oxygen atom in CH3CHO?

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
31. What is the hybridization of the ntrogen atom in (CH3)2CHCN?

32. How many π bonds are present in the following molecule?

33. Which of the molecules below can be properly called an ether?

A. CH3CH2CH(CH3)2
B. CH3OCH2CH2CH3
C. CH3COOH
D. CH3COOCH3
E. HCCCH3

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
37. What is the name of the functional group found in the molecule CH3CH2COOH?

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.

42. Which of the following is a secondary alkyl halide?

A. methyl bromide
B. isopropyl chloride
C. tert-butyl iodide
D. propyl bromide
E. isobutyl chloride

43. Provide the structure of 1-bromo-3-methylhexane.

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
1. Propose a substitution mechanism (SN1 or SN2) and the resulting product for the following
reactions. Pay special attention to stereochemistry.

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

1. Is the molecule shown below chiral or achiral?

OH

OH

2. Is the molecule shown below chiral or achiral?

H
CH3
C C C
H CO2H

3. Is the molecule shown below chiral or achiral?

CH2OH
HO2C
H CO2H

4. Is the molecule shown below chiral or achiral?

Cl

5. Is the molecule shown below chiral or achiral?

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk
7. Label each asymmetric carbon in the compound below as R or S.

Me
OH

8. Label each assymetric carbon in the compound below as R or S.

Cl

9. Draw the structure of (2R,3S)-2,3-dichloropentane. Take particular care to indicate three

dimensional stereochemical detail properly.

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

Stellios Arseniyadis, PhD, FRSC

Department of Chemistry, School of Biological and Chemical Sciences, Queen Mary University of London
Joseph Priestley Building, Mile End Road, London E1 4NS, United Kingdom, Tel: +44 (0)207 882 8445, Mail : s.arseniyadis@qmul.ac.uk