Review Worksheet for Final Exam (Ch. 11-15, 17 and 19)
Chem 102, Fall 2005
1. For each of the following compounds, write the electron-dot structure (show all nonbonded electron pairs) and classify the compound as polar or nonpolar:
a) CS2
b) CH3COOH
c) CH3NH2
2. Classify each of the following as an organic or inorganic compound:
a) CH3OH
b) NH3
c) SiO2
3. Identify each of the following compounds by functional group:
OH
OH
N
O
O
O
4. Explain why CH4 is tetrahedral rather than flat.
CH3
5. Draw the structures for all of the constitutional isomers for each of the following
molecular formulas:
a) C4H10O (alcohols)
b) C6H12O (ketones)
c) C5H10 (alkenes) *also include all cis-trans isomers
6. Classify each of the carbons in the molecule below as 1, 2, 3 or 4:
7. Give a name for each of the following structures:
O
OH
a)
b)
c)
N
Cl
OH
CH3
d)
e)
f)
O
O
g)
h)
N
i)
O
NH2
j)
k)
SH
l)
Br
OH
O
H
m)
n)
o)
O
O
O
O
O
O
p)
OH
q)
O
r)
O
F
8. Draw the structure for each of the following names:
a) diphenyl ether
b) 3-pentanone
c) sodium acetate
d) cis-3-hexene
e) isopropyl butanoate
f) N,N-dimethylformamide
g) 2-hydroxypyridine
h) acetaldehyde
i) pyrrole
9. Give the major product(s) for each of the following reactions:
O
NaBH4
a)
H
O
Tollens
b)
H
O
PCC
c)
H
O
H3O+
d)
H
O
NaBH4
e)
O
Tollens
f)
O
g)
h)
+
2
OH
2 CH3OH
H3O+
heat
i)
2
SH
OH
j)
CrO3
H3O+
OH
k)
I2
H3O+
heat
Acid Cat.
Br2
l)
H2
m)
Pt
HBr
n)
H3O+
o)
HNO 3
p)
H2SO4
SO3
q)
H2SO4
CH3
Br2
r)
FeBr3
Br2
s)
Light
CH3
Br2
t)
Light
O
Acid cat.
u)
H
OH
O
H3O+
OH
v)
+
Heat
OH
O
w)
+
NH3
Heat
OH
O
H3O+
x)
O
Heat
O
y)
NaOH
H
O
O
HCl
z)
H2O
N
H
O
NaOH
aa)
NH2
bb)
OH
cc)
OH
PCC
CrO3
H3O+
OH
PCC
dd)
OH
ee)
CrO3
H3O+
10. Give the monomer that would form each of the following polymers:
Br
Br
Br
a)
CH3
Cl Cl
CH3
Cl Cl
CH3
Cl Cl
b)
11. Write and balance the combustion reaction for each of the following compounds:
a) (benzene) C6H6
b) (glucose) C6H12O6
c) (ethanol) C2H6O
12. Which has the higher boiling point, ethylmethylamine or trimethylamine? Explain,
using drawings to illustrate your answer.
13. Rank the following compounds in order of increasing boiling point (number 1-6 =
lowest to highest):
O
NH2
N
N
H
H
N
OH
O
14. Which would be more soluble in water, benzoic acid or sodium benzoate? Explain,
using drawings to illustrate your answer.
15. Circle the compounds that are soluble in water. Include those that are only slightly
soluble.
O
OH
OH
CH3
O
H
O
O
O
N
O
N
H
H
16. First write the reaction, and then write the arrow-pushing mechanism, for the
ionization of each of the following compounds in water:
a) phenol
b) acetic acid
c) dimethylamine
17. Give the carboxylic acid and the alcohol that would be needed to form each of the
following esters (using Fischer esterification):
O
H2SO4
a)
O
Heat
O
H2SO4
b)
O
Heat
O
H2SO4
c)
Heat
H2SO4
H
O
O
d)
Heat
O
18. Draw the enantiomer for each of the following compounds:
H
a)
CH3
NH2
Br
H Br
b)
CH3
HO
Br H
F
HO
H
c)
H
OH
Cl
CH3
d)
HO
H
Br
19. State the relationship of each of the following pairs of compounds (identical,
enantiomers or diastereomers):
NH2
a)
NH2
CH3
OH
H
H
OH
H 3C
Br
H
b)
CH3
H
Cl
CH3
Cl
Br
H Br
Br H
OH
c)
CH3
H 3C
HO
Br H
Br H
CH3
CH3
H
OH
HO
H
OH
H
H
d)
CH3
OH
CH3
CH3
CH3
Br
H
H
Br
Br
H
H
Br
e)
CH3
CH3
OH
H
H
H
OH
f)
H
OH
H
H
H
OH
H
H
H
H
OH
H
HO
H
g)
OH
H
H
H
OH
20. Draw the most stable conformation of butane, either using wedges and dashes, or a
Fischer projection (you may draw methyl groups as –CH3):
21. Draw the Fischer projection for each of the following:
Br
a)
CH3
F
HO
H
b)
CH3
Br
Cl
Br H
c)
CH3
H 3C
H Cl
Br H
d)
Br
H 3C
HO H
HO H
e)
H
OH
O
H OH
22. When 1-butene is reacted with water and an acid catalyst, the major product is 2butanol rather than 1-butanol. Explain why using drawings (chemical structures) to
support your explanation.