What to Review from Gen Chem
Chem 109A will move quickly through Chapter 1 and the first half of Chapter 3. Much of the material
covered in these chapters is a review of what you have learned in general chemistry. Prior to our first
lecture meeting, please review Chapter 1 in the Bruice text on your own. A list of important topics that
you should be comfortable with is found below. To help you gauge your preparation, we have
included a set of practice problems that you should complete prior to our first meeting.
After the practice problems covering the Chapter 1 review material you will also find a list of topics
and problems covering the nomenclature that you learned in Chem 1C, which is part of the material
discussed in Chapter 3 in the Bruice textbook. It is not critical that you review nomenclature prior to
our first lecture meeting, but be aware that we will not spend time in lecture on this material and you
should go through it on your own, ideally by the time we finish Chapter 2.
Chapter 1
1. Structure of an atom (Chapter 1.1-1.2)
You should be able to:
• Determine the number of protons, neutrons, electrons, atomic number, mass number in an
atom or ion.
• Write electronic configurations (at least the first 20 elements of the periodic table)
• Determine the number of valence electrons (at least the first 20 elements of the periodic
table)
• Determine the atomic mass of an element
2. Covalent bonds (Chapter 1.3)
You should be able to:
• Determine types of bonds
• Indicate/show the direction of bond polarity using electronegativity values
• Calculate the partial negative charge on electronegative atoms (or % ionic character of a
bond) given the observed dipole moment.
3. Drawing organic molecules. (Chapter 1.4; this may be briefly reviewed in lecture)
You should:
• Differentiate between bonding electrons and non-bonding electrons
• Be able to draw the different representations of compounds, including those with double
and triple bonds (Kekulé structures, Lewis structures, condensed structures, skeletal
structures).
• Be able to assign formal charge.
4. Atomic orbitals and molecular orbital theory. (Chapter 1.5-1.13; this may be briefly reviewed
in lecture)
You should:
• Be able to recognize the different atomic orbitals.
• Understand how a sigma bond is formed.
• Understand how bonding and antibonding molecular orbitals are formed and their
differences.
• Understand formation of a pi bond.
•
Understand the formation of bonds in methane (single bonds), ethene (double bonds), and
ethyne (triple bonds)
Understand the bonds in the methyl cation, methyl radical, and the methyl anion.
Understand the bond in a hydrogen halide.
•
•
5. Hybridization and molecular geometry. (Chapter 1.14-1.16; this may be briefly reviewed in
lecture)
You should:
• Be able to predict the orbitals used to form a given bond
• Be able to describe bond angles in a molecule.
• Be able to determine the hybridization and geometry of an atom.
Review practice problems:
1. How many protons and neutrons does oxygen-18 have?
2. How many protons and electrons does Na+ have?
3. How many valence electrons does fluorine have?
4. Write the ground state electronic configuration for bromine.
5. Which of the following has the most polar bond?
NaI
LiBr
Cl2
KCl
6. Use the symbols d+ and d- to show the direction of polarity of the indicated bond in the following
compounds
H3C Li
H2N OH
7. Label the following as either polar covalent, nonpolar covalent or ionic bonds
C H
O H
H F
8. Draw the molecule below in 3D representation (perspective formula) and indicate the approximate
C-N-H bond angle.
(CH3)2NH2
9. a) For each of the following give each atom the appropriate formal charge (a formal charge of zero
is assumed if no charge is indicated).
H
H N
H
H
B H
H 3C
H
O
C
O
O
O N O
H3C O CH3
H
H 3C O
H
H O
10. a) Assign a formal charge to all carbon atoms in each of the following (a formal charge of zero is
assumed if no charge is indicated).
H
H C
H
H
H C
H
H2C CH
H2C CH
H C H
b) Fill in any missing formal charge(s) on the molecule below. Assume each atom has a complete
octet.
OH
NH
HO
11. Represent the following condensed structure as:
(CH3)3C(CH2)3CHO
a) a Kekulé structure
b) a Lewis structure
c) a skeletal structure
12. Do the sp2 carbons and the indicated sp3 carbons have to lie in the same plane?
H
CH3
C C
H
H 3C
13. Predict the approximate bond angles in the methyl radical.
14. In what orbitals are the lone pairs in the following molecules:
a) CH3OH
b) CH3CN
15. What is the hybridization of each of the C, N, and O atoms in the following compound?
O
N
CH3
Organic Chemistry Nomenclature (Chapter 3.1-3.6) You will not be tested on naming until quiz 2)
You should be able to:
1. Name alkanes (including cycloalkanes)
2. Name alkyl halides
3. Name ethers
4. Name alcohols
Note: you will also learn how to name amines (Chapter 3.7), although that was not
discussed in general chemistry.
1. Provide a systematic (IUPAC) name for each of the following:
a)
OH
b)
c)
O
d)
e)
Cl
2. Draw the skeletal structure for each of the following:
a) 5-ethyl-2-methyloctane
b) 2,3,3,4-tetramethylheptane
c) 2,6-dimethyl-4-(2-methylpropyl)decane
d) (1-bromoethyl)cyclopentane
3. Each of the following IUPAC names is incorrect. Give the correct IUPAC names.
a) 4-methylpentane
b) 2,3,3-trimethylbutane
c) 4-bromo-3-pentanol