CEM143, Problem Set #1
Chapters 1-2
1.
Draw Lewis dot structures and stick structures of the following compounds and calculate the
formal charge for the indicated atoms:
Lewis Structures
H
H
C
CH3I
I
H
H C I
H
H
H
H N H
H
H
H N H
H
H
H
N
NH3
Stick Structures
Formal Charges
C=0
N=0
H
H
H
NH4
N
H
H
CH3NO2
H
C
O
N
O
H
CH2N2
H O
H C N
O
H
H
H
C
H
N
N
C N N
H
N = +1
N = +1
C=0
2.
Draw a resonance structure for the following compounds:
O
H3C C O
O
H3C C O
O
H3C C NH2
O
H3C C NH2
O
H 3C C O
O
H3C C NH2
O
H 3C N O
O
H 3C N O
O
H3C N O
OH
H3C C H
OH
H3C C H
3.
OH
H 3C C H
Convert the following structural (stick) formulas into line formulas and name the
compounds:
CH3 CH3
CH3CH2CHCH2CCH3
CH3
2,2,4-trimethyl hexane
CH3 CH2CH2CH3
CH3C
CHCH2CH3
CH3
3-ethyl-2,2-dimethylhexane
Br
Br
Br CH2C CHCH2CH3
CH3 CH2CH2CH2CH2CH3
Br
1,2-dibromo-3-ethyl-2-methyl octtane
H2C CH2
CH2
H3C C
H CH
CH2CH2CH3
2-methyl-1-propyl cyclopentane
CH2CH2CH2CH3
H2CHC
H2C CH2
butylcyclobutane
4. Draw the structures that correspond to the following names:
butyl bromide
Br
t-butyl chloride
Cl
iso-propyl chloride
Cl
sec-butyl iodide
5. Provide the chemical formulas for:
I
Br
C8H18
C9H16
C12H23Br
C10H18
C15H30
6. Draw all possible tribromopropanes:
propane
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br