CHEM 234 – Bonding – Extra Practice

CHEM 234 – Bonding – Extra Practice
1. Draw Lewis dot structures including all of the resonance structures (if there is more than one), the resonance
hybrid, and the orbital overlap diagrams for the following compounds or ions:
formaldehyde, H2CO
carbon dioxide, CO2
Compare the CO bond lengths in the three species.
2. Explain why BF3 has no dipole moment while NF3 does.
bicarbonate HCO3–
3. Draw a bond-line formula for an isomer of C5H12O that is: A) a secondary alcohol. B) a tertiary alcohol.
4. Draw a bond-line formula for an isomer of C4H8O that is: A) an ether. B) a ketone. C) an aldehyde.
5. Draw a bond-line formula for an isomer of C6H12O that:
A) includes a 5 or 6-member carbon ring.
B) contains a carbonyl.
6. Put the following in order of highest BP to lowest BP. Explain your ordering.
Ethyl methyl ether, CH3CH2OCH3
Propyl alcohol, CH3CH2CH2OH
Trimethyl amine, (CH3)3N
7. Draw all of the reasonable resonance structures for the following species:
A
B
D
C
O
E
F
O
SEE THE FOLLOWING PAGES
O
#7 Continued
8. For each of the following pairs of structures, circle the best description of the relationship of the
structures.
A)
F
F
C
H
F
H
F
H
Same
compound
B)
C
H
Constitutional
(structural) isomers
cis-trans
isomers
Compounds with different
formulas (NOT isomers)
F
H
H
F
F
F
H
H
Same
compound
Constitutional
(structural) isomers
cis-trans
isomers
Compounds with different
formulas (NOT isomers)
H
C)
H
H
H
H
H
C
C
C
C
H
C
H
H
H
H
C
H
H
H
Same
compound
Constitutional
(structural) isomers
cis-trans
isomers
Compounds with different
formulas (NOT isomers)
Same
compound
Constitutional
(structural) isomers
cis-trans
isomers
Compounds with different
formulas (NOT isomers)
D)