CHEM 232 A Review of General Chemistry Problem Set Chapter 1

1. Rank the items in each set below according to the trends observed for the physical and chemical properties
indicated.

A. Rank the atoms in bold in order of increasing value of their formal charge (1 = most negatively charged; 4
= most positively charged). All lone electron pairs are shown for all atoms. Assume no implicit Hs on bold
atoms.

B.

C.

N N N N N N N N N P CH3
Me Me Me
CH3

D. The skeletons (atoms and single bonds only) have been drawn for four molecules below. Rank them in
order of increasing number of remaining electrons that must be added to each as bonded or lone electron
pairs to complete the Lewis structure (1 = least remaining electrons; 4 = most remaining electrons).
Assume each molecule is neutral unless otherwise indicated.

3–
O
P H
O
Cl Be Cl O O S O H B
O H

1
E. Rank in order of increasing polarity of the bond (1 = smallest dipole moment; 5 = largest dipole moment).

F. Rank in order of increasing polarity of the bond (1 = smallest dipole moment; 5 = largest dipole moment).

G. Rank the molecules in in order of increasing strength of intermolecular forces.

O
HO OH H CH3
F F O O C O
H 3C CH3 OH

H. Rank in order of increasing boiling point (1 = lowest boiling point, 5 = highest boiling point).

Cl Cl
Cl CH3 H 3C H 3C
H 3C H 3C Cl H 3C O CH3
Cl Cl

I. Rank in order of increasing boiling point (1 = lowest boiling point, 5 = highest boiling point).

OH Br

2
2. For each of the following structures:

a. Draw out all implicit hydrogen atoms and lone pairs of electrons
b. Draw dipole arrows for any polar-covalent bonds
c. Predict the overall dipole for the molecule, if any

SH F
H 3C N
H 3C CH3 F
F CH3

N
O C

O
H 3C Cl H 3C Li S
H 3C

O
OH

3
3. For each of the following structures:

a. Identify any polar covalent bonds

b. Draw partial charges consistent with your expected polarization

O S
O O

H
O O H O
Cl
N
H CH3

Br
O O
H P
O CH3 H 3C CH3
CH3

N O
C
S O
H 3C CH3 H 3C H

4
4. For the indicated atoms in the following molecules:

a. Identify the hybridization state of the atom

b. Predict the geometry of the atom
c. Predict the bond angles around this atom

5. For the indicated bonds in the following molecules:

a. How many sigma bonds are present?

b. How many pi bonds are present?

N N O OH

N N

O
N

5
6. Draw all possible isomers for the following chemical formulas.

A. C2H7N

B. C4H8

C. C4H10O

D. C2H4Cl2

6
7. Determine the formal charge expected for the indicated atoms.

8. Draw the orbital interaction that occurs between the two shown orbitals. Clearly indicate any nodal planes.

H H

7
 H H

H
C H
H

C O
H
H
H

8
H H
C C
H H

H H
C C
H H

H H
C C
H H

N C H