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CHEM 10052
Spring 2000
Exam #1
Name______________________
ss#________________________
1. The following molecule contains five different functional groups. Circle and identify
all of the functional groups in this compound. (10 pts.)
O
O
HO
O
N
2. Give examples of compounds that contain the following functional groups (10 pts.).
a) amide
b) alkyne
d) sulfide
e) ether
c) aldehyde
2
3. Name the following compounds using either common nomenclature or IUPAC
systematic nomenclature (10 pts).
NO 2
CH
CH CH
3
CH3 CH2 CH2 CH2 CH3
CH3 CHCH2CH3
a)
CH3
d)
C
b)
CH 3
C C CH
CH 2 CH 3
2
H
CH3
3
C
c)
H
CH3
e)
4. Draw structural formulas for the following compounds (10 pts):
a) cyclobutane
d) cis-2-butene
b) 2-bromo-2-methylpentane
c) 2-hexyne
e) trans-1, 3-dimethylcyclohexane
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5. Using an orbital diagram describe the bonding in a triple bond. Label the  and 
bonds, indicate bond angles, and describe the molecular geometry and orbital
hybridization. (8 pts.)
6. Draw and name three isomers with the molecular formula C5H10. (9 pts).
7. Draw Lewis Structures for the following. Draw at least one stable resonance form
that may exist and include formal charges for all atoms in the structure. Circle the
most stable resonance form in cases where there are differences. (8 pts.)
a. SCN–
b. NO2
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8. Describe the structural and physical properties of hydrocarbons (alkanes, alkenes,
and alkynes) as compared to water. Include descriptions of hybridization, molecular
geometry, melting point, boiling point, hydrogen bonding, solubility etc. (7 pts.)
9. Predict the products of the following reactions. Indicate major and minor products
where appropriate. (2 pts. each).
CH3
CH CH3+ Br2
a. excess CH3
CH3
H
C
b.
light
H2
Pt
C
H
H
Br2
c.
+ excess Cl 2
d.
CH3
H
C
e.
f.
H
CH 3
+
H
C
H
H2O
C C CH3 + O2
OH
g.
light
H2SO 4

spark
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10. Supply the reagents required to complete the following transformations (2 pts. ea.)
OH
CHCH3
a.
CH3
H
C
b.
H
C
CH 3CH 2CH 2CH 2CH 3
CH2 CH3
11. Give a detailed mechanism for hydration of propene. Explain why one possible
product is formed in preference to the other possible product. (8 pts.)