CHEM 301 - Dr. Hartel
Winthrop University
Self Evaluation 1
1. Atoms and Orbitals
a. Using horizontal lines and arrows, draw an accurate ground state electronic configuration of
silicon. Label each orbital and clearly show relative energies.
3p
3s
2p
2s
1s
b. Provide the orbital hybridization of the indicated atoms.
sp2
CH3
sp
H
H
C
C
C
H
C
CH3
H
H
CH2
C
H
CH3
sp
C
C
sp3
sp2
H
O
CH2CH3
C
H
sp3
sp3
H3C
CH3
CH3CH2
sp3
3
sp
c. Describe the two orbitals that overlap to form the bonds indicated by each arrow.
H
B
H
C+D
E
(s - sp3)
A _________________
(s -sp2)
B _________________
(p - p)
C _________________
(sp2 - sp2)
D _________________
* C + D comprise a double bond.
Assign C as the weaker bond of the two.
(sp3 - sp3)
E _________________
1
CH2CH3
CH2CH3
sp2
A
N
CHEM 301 - Dr. Hartel
Winthrop University
Self Evaluation 1
2. Lewis Structures
Draw complete Lewis structures for each of the following species.
C3H5F
LiAlH4
CH3CH2NO2
H
Li+
H
Al
H
H
H
H
H
C
C
H
H
N2O
(No Charges)
H
O
N
F
C
N
H
O
C
H
N
O
or
C
H
N
H
N
O
3. Nomenclature
Give the proper IUPAC name for each of the following structures on the lines provided.
O
CH3CH2CH2
1-ethyl-2-(2-methylpentyl)cyclohexane
CH2CH(CH3)2
2-methyl-1-propoxypropane
Br
3-bromo-5methyl-4-(1-methylethyl)heptane
Br
OCH2CH3
Br
OH
5-methyl-3-hexanol
8-ethoxy-4-ethyl-1,6-nonadiene
3,3-dibromocyclooctene
OH
CH3
CH2CH2CHFCH2CH3
N
C
C
3-ethyl-5-methyl-1-heptyne
H
2-(1-methylethyl)-1-hepten-4-ol
2
H
3-fluoro-N-methyl-1-pentanamine
CHEM 301 - Dr. Hartel
Winthrop University
Self Evaluation 1
4. Terminology
For each compound below, indicate the degree of substitution at the carbon indicated with an
arrow. Identify the class of each compound (amine, alkyl halide, etc.) and the type as appropriate
for the class (primary, internal, disubstituted, etc.).
2o
methyl
4o
OH
3o
CH3
N
Cl
H
alkyl halide
amine
alkene (cycloalkene)
Class
Class
tertiary
secondary
disubstituted
primary
Type
Type
Type
Type
alcohol
Class
Class
5. Dipoles and Physical Properties
a. Use symbols (δ+ and δ-) to designate the dipoles of the indicated bonds for each molecule.
Rank the bonds in each set in order of decreasing polarity (1 most polar to 3 least polar).

Na

H

Li
2

H

K

H
1
3

F
none
Cl
Cl

NH2
1
3
O
4
2
CH3
N
H
1
5
3
F

OCH3
2
b. Rank each from HIGHEST boiling point (1) to LOWEST boiling point (5).
3

CHEM 301 - Dr. Hartel
Winthrop University
Self Evaluation 1
6 . Application of Concepts
a. Before you are three bottles, each containing a clear, colorless liquid. One bottle contains
pentane, another contains heptane and the remaining contains 1-hexanol. Using concepts
discussed so far in class, how can you determine which compound is in each bottle? Explain
your plan and rationale.
OH
Because of the differences in size and functional groups, these compounds will have very
different boiling points. One could simply determine the boiling point of the liquid from each
bottle, and know that the highest boiling must be 1-hexanol (large and capable of hydrogen
bonding) and the lowest boiling must be pentane (smallest and lacking other strong
intermolecular forces). The remaining liquid is therefore heptane.
b. Draw the structure of the only acyclic (no rings) 7-carbon tertiary alcohol that also has a
quaternary carbon.
OH
c. Draw the Lewis structure for methanamine hydrochloride (CH3NH3+ Cl-).
H
H
H
C
N
H
H
H
Cl
How many electrons are in this compound? 36 electrons
How many valence electrons are in the cation? 14 electrons
Assuming the most abundant isotopes, how many neutrons are found in this compound? _31_
How many molecular orbitals are in the cation? 14 MOs (7 bonding and 7 antibonding)
How many total bonding interactions are there in this compound? 8 (7 covalent and 1 ionic)
4