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
S
C
b) CH3COOH
S
H
Nonpolar
H
O
C
C
c) CH3NH2
H
O
H
H
C
N
H
H
H
Polar
Polar
H
2. Classify each of the following as an organic or inorganic compound:
a) CH3OH
b) NH3
c) SiO2
Organic
Inorganic
Inorganic
3. Identify each of the following compounds by functional group:
OH
OH
CH3
N
cycloalkane
phenol
amine
alcohol
O
O
O
alkene
ether
aromatic hydrocarbon
ketone
alkyne
4. Explain why CH4 is tetrahedral rather than flat.
According to VSEPR theory, pair of electrons attached to a central atom repel each other
and so will move as far apart from each other as possible. This determines the shape
(molecular geometry of a molecule). With four different groups attached to the central
carbon in CH4, the shape is tetrahedral because this gives bond angles of around 109.5,
which is as far apart as the electron pairs can get. If flat, CH4 would have bond angles
of only 90, so the electron pairs would be closer together, causing more repulsion.
5. Draw the structures for all of the constitutional isomers for each of the following
molecular formulas:
a) C4H10O (alcohols)
OH
OH
OH
OH
b) C6H12O (ketones)
O
O
O
O
O
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:
1
3
2
1
1
4
2
3
3
2
1
1
3
1
7. Give a name for each of the following structures:
O
OH
a)
b)
c)
N
Cl
para-chloroanisole
trimethylamine
OH
phenol
CH3
d)
e)
f)
3-hexyne
cyclohexanol
toluene
O
O
g)
h)
N
i)
O
trans-2-butene
1,4-dioxane
N,N-dicyclopropylacetamide
NH2
j)
k)
SH
l)
Br
2-methyl-1-propanethiol
ortho-bromoanaline
3-tert-butyl-5-isopropyltoluene
OH
O
H
m)
n)
o)
O
O
propyl propanoate
cyclopentene
4-hydroxypentanal
O
O
O
O
p)
OH
q)
O
r)
O
3,4-dioxohexanoic acid
cyclobutanone
F
methyl-3-fluorobenzoate
8. Draw the structure for each of the following names:
a) diphenyl ether
O
b) 3-pentanone
O
c) sodium acetate
O
O
Na
d) cis-3-hexene
e) isopropyl butanoate
O
O
f) N,N-dimethylformamide
O
N
g) 2-hydroxypyridine
N
OH
h) acetaldehyde
O
H
i) pyrrole
N
H
9. Give the major product(s) for each of the following reactions:
O
NaBH4
a)
OH
H
O
O
Tollens
b)
OH
H
O
PCC
c)
NR
H
O
H3O+
d)
HO
OH
H
H
O
OH
NaBH4
e)
O
Tollens
f)
NR
O
g)
h)
+
2
OH
2 CH3OH
O
Acid Cat.
H3O+
O
Heat
i)
2
SH
I2
S
S
OH
j)
CrO3
H3O+
OH
Acid Cat.
k)
Heat
NR
O
Br
Br2
l)
Br
CH3
H2
m)
Pt
n)
o)
CH3
HBr
Br
H3O+
OH
NO2
HNO 3
p)
H2SO4
SO3 H
SO3
q)
H2SO4
CH3
CH3
Br2
CH3
r)
+
FeBr3
Br
Br2
Br
Br
s)
Light
H
CH3
Br2
t)
Light
H
C
Br
O
O
OH
Acid cat.
u)
H
OH
O
H3O+
OH
v)
O
+
Heat
OH
O
O
O
w)
+
Heat
NH3
NH2
OH
O
O
HO
+
H3O
x)
OH
O
+
Heat
O
O
y)
NaOH
H
H
O
O
Na
O
HCl
z)
H2NCH3
+
H2O
N
H
OH
O
O
NaOH
aa)
+
NH2
O
O
bb)
OH
PCC
H
CrO3
cc)
OH
O
H3O+
OH
O
OH
PCC
dd)
OH
ee)
HO
+
O
CrO3
H3O+
O
Na
NH3
10. Give the monomer that would form each of the following polymers:
Br
Br
Br
Br
H
a)
H
CH3
CH3
CH3
CH3
Cl
Cl Cl
Cl Cl
Cl Cl
H
b)
Cl
H
11. Write and balance the combustion reaction for each of the following compounds:
a) (benzene) C6H6
2C6H6 + 15O2  12CO2 + 6H2O
b) (glucose) C6H12O6
C6H12O6
+
6O2
c) (ethanol) C2H6O
C2H6O
+


3O2
6CO2
2CO2
+
+
6H2O
3H2O
12. Which has the higher boiling point, ethylmethylamine or trimethylamine? Explain,
using drawings to illustrate your answer.
Ethylmethylamine has the higher boiling point because it’s secondary, and can
H-bond with itself, while trimethylamine is tertiary, so it can’t H-bond with itself.
N
H
N
N
H
N
N
H
13. Rank the following compounds in order of increasing boiling point (number 1-6 =
lowest to highest):
O
NH2
N
N
H
4
6
H
N
1
OH
3
5
O
2
14. Which would be more soluble in water, benzoic acid or sodium benzoate? Explain,
using drawings to illustrate your answer.
Sodium benzoate is more soluble in water because it is fully ionized, while
benzoic acid is only slightly ionized in water.
O
O
H2O
Na
O
+
O
O
Na
O
+
OH
H 2O
H 3O +
+
O
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
N
H
O
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
OH
O
H2O
+
H3O+
+
O
O
H
H
O
+
H
+
H
O
H
H
b) acetic acid
O
O
+
H2O
H3O+
+
O
OH
O
O
H
O
+
H
O
H
+
H
O
O
H
H
c) dimethylamine
H
H
N
H2O
+
H
+
N
H
H
N
H
O
+
H
+
N
H
HO
H
O
17. Give the carboxylic acid and the alcohol that would be needed to form each of the
following esters (using Fischer esterification):
O
O
a)
CH3OH
+
OH
H2SO4
O
Heat
O
O
H2SO4
HO
+
b)
O
Heat
OH
O
O
H2SO4
c)
+
H
Heat
HO
OH
O
H2SO4
+
d)
OH
HO
Heat
H
O
O
O
18. Draw the enantiomer for each of the following compounds:
H
H
a)
CH3
NH2
Br
H 3C
H 2N
H Br
b)
Br
Br H
CH3
H 3C
HO
OH
Br H
H Br
F
HO
F
H
H
OH
c)
H
OH
HO
Cl
Cl
CH3
CH3
d)
HO
H
Br
H
H
OH
Br
19. State the relationship of each of the following pairs of compounds (identical,
enantiomers or diastereomers):
NH2
NH2
a)
CH3
OH
H
Br
Enantiomers
H
OH
H 3C
H
b)
CH3
H
Cl
H Br
Br H
OH
c)
Identical
CH3
Cl
Br
CH3
H 3C
Diastereomers
HO
Br H
Br H
CH3
CH3
H
OH
HO
H
OH
H
H
d)
Diastereomers
CH3
OH
CH3
CH3
CH3
Br
H
H
Br
Br
H
H
Br
e)
CH3
CH3
OH
H
Identical
H
H
OH
OH
f)
Diastereomers
H
H
H
OH
H
H
OH
H
H
HO
H
H
g)
Enantiomers
H
H
OH
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):
H
H
CH3
H 3C
H
H
21. Draw the Fischer projection for each of the following:
Br
Br
a)
HO
CH3
F
HO
CH3
H
H
Cl
b)
Br
CH3
Br
Cl
CH3
CH3
Br H
c)
CH3
H 3C
H
Br
Cl
H
H Cl
CH3
CH3
Br H
d)
F
Br
H 3C
H
Br
H
OH
HO H
Br
O
H
H
OH
HO H
e)
H
OH
O
HO
H
H OH
HO
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.
The carbocation intermediate is more stable in the secondary position, so that is the one
that forms, leading to the secondary alcohol product (Markovnikov’s rule).
H3O+
OH