Name:________________________________
_____
Chemistry 30
Organic Chemistry Workbook
Structural Isomers
1. Build the two isomers of butane, C4H10. Draw the complete, condensed and line structural
diagrams for each isomer.
2.
Build the two isomers of C2H6O. Draw the complete and condensed structural diagrams for each
isomer.
3.
Build the two isomers of C2H7N. Draw the complete and condensed structural diagrams for each
isomer.
4.
Draw two isomers of C4H10O. The boiling points of the two compounds differ by approximately
70C. Which one would have the highest boiling point? Explain why the boiling points are so
different.
Alkanes
1.Draw and name the five possible noncyclic isomers of C6H14.
2. Name the following compounds:
a)
CH3 – CH2 – CH2 – CH3
b)
CH2 – CH2 – CH2 – CH2 – CH3
CH2 – CH2 – CH3
CH3
c)
d)
CH3 – CH2 – C – CH2 – CH2 – CH3
CH3
CH3 – CH2 – CH2 – CH2 – CH – CH3
CH3
C2H5
e)
f)
CH3 – CH – CH – CH – CH2 – CH2 – CH3
CH3
CH2 – CH2 – CH3
C3H7
Chem 30 Organic Chemistry Workbook
CH3 – CH2 – CH – CH2 – CH3
1
g)
CH3 – CH – CH2 – CH2 – CH3
CH2 – CH3
h)
CH3 – CH2 – CH – CH2 – CH2 – CH3
CH2 – CH2 – CH3
CH2 – CH3
3. Why is the name 2-ethyl-2,4-dimethylhexane unsuitable for the following compound?
What is the correct name of the compound?
CH3
CH3
CH3
C
CH2
CH
CH2
CH3
CH2
CH3
4. Draw each of the following compounds:
a) 3-ethylhexane
b) 2,4-dimethylheptane
c) 3,4-diethyl-3-methylhexane
d) 3-ethyl-4,5-dipropyloctane
e) 2,2-dimethylpentane
f) octane
g) 2,2,3,3,4,4-hexamethyloctane
h) 4-ethyl-4-propylheptane
Cycloalkanes
1. Name each of the following compounds:
a)
b)
CH3
CH3
c)
d)
CH2 – CH2 – CH2 – CH3
Chem 30 Organic Chemistry Workbook
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CH3
CH2 – CH3
CH3
CH3
e)
CH2 – CH2 – CH3
f)
CH2 – CH3
CH2 – CH2 – CH3
CH3
CH3
2. Draw each of the following compounds:
a) propylcyclopentane
b) 1-ethyl-4-methylcyclohexane
c) 1,1-diethylcyclobutane
d) 1,2-diethyl-3-propylcyclobutane
e) 1,6-diethyl-3,4-dimethyl-1-propylcyclooctane
f) cyclobutane
Alkenes
1. Draw and name the five possible noncyclic isomers of C5H10.
2. Name the following compounds:
a)
CH2 = CH2
b)
c)
d)
CH2 = CH – CH2 – CH3
e)
CH2 = CH – CH3
CH2 – CH = CH – CH3
CH3
CH2 – CH3
f)
CH3 – CH2 – C = CH2
CH3 – CH2 – C = C – CH2 – CH3
CH2 – CH3
g)
CH3 – CH – CH2 – CH2 – CH3
h)
CH3 – CH = C – CH2 – CH3
CH – CH2 – CH3
CH = CH – CH3
CH3
3. Draw each of the following compounds:
a) oct-3-ene
b) 2,4-dimethylpent-2-ene
c) 4-ethyl-3-methylhex-2-ene
d) methylpropene
e) 3-ethylpent-1-ene
f) ethene
g) 5-ethyl-2,2,6-trimethylhept-3-ene
h) 5-ethyl-3,4,6-trimethyloct-2-ene
Chem 30 Organic Chemistry Workbook
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Cycloalkenes
1. Name the following compounds:
a)
b)
c)
d)
CH2 – CH2 – CH3
CH2 – CH3
C2H5
CH2 – CH3
CH3
CH3
2. Draw the following compounds:
a) cyclooctene
b) 1-ethyl-3-methylcyclopropene
c) 3,3-dimethyl-1-propylcyclopentene
d) 4-butyl-1-methylcyclohexene
Alkynes
1. Draw and name the three possible noncyclic isomers of C5H8.
2. Name the following compounds:
a)
CH ≡ CH
b)
c)
d)
CH ≡ C – CH2 – CH3
e)
CH ≡ C – CH3
CH3 – C ≡ C – CH3
CH2 – CH3
f)
CH ≡ C – C – CH3
CH2 – CH3
CH3 – CH – C ≡ C – CH2 – CH3
3. Draw the following compounds:
a) non-3-yne
b) 5-ethyl-4-propylhept-2-yne
c) 4,4-diethylhex-1-yne
d) 2,2,3,3-tetramethyloct-4-yne
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Aromatics
1. Draw and name the three possible isomers of C6H4(CH3)2.
2. Name the following compounds:
a)
CH3
CH2 – CH3
b)
c)
d)
CH2 – CH2 – CH3
CH3 – CH2 – CH – CH3
CH2 – CH2 – CH3
CH3
CH3
CH3
e)
CH3
f)
CH3
CH2
CH2 – CH – CH3
CH3 – CH2 – CH – CH2 – CH3
g)
h)
C2H5
C2H5
CH3
C3H7
CH3
CH3
3. Draw the following compounds:
a) 1-methyl-3-propylbenzene
b) methylbenzene (toluene)
c) 2,2-dimethyl-3-phenylhexane
d) phenylethene
e) ethylbenzene
f) 4-phenyl-5-propyloctane
g) 1,4-diethylbenzene
h) 4-methyl-2-phenylpent-2-ene
Chem 30 Organic Chemistry Workbook
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4. Give two reasons why 1-methyl-3,4-diethylbenzene is an unsuitable name. Draw this
compound and give the correct name.
Alcohols
1. Name the following compounds:
a)
CH3 – OH
b)
c)
d)
CH3 – CH2 – OH
OH
CH3 – CH2 – CH2 – OH
CH3 – CH – CH2
OH
e)
CH3
f)
CH3 – CH – CH – OH
OH
OH
g)
h)
OH
OH
2. Draw each of the following compounds:
a) butan-1-ol
b) 2-methylbutan-2-ol
c) 4-ethyl-2-methylhexane-3,3-diol
d) 2-phenylpentan-3-ol
e) 4-ethyl-2-methylphenol
f) 2-methylcyclopropanol
Chem 30 Organic Chemistry Workbook
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Organic Halides
1. Name the following compounds:
a)
CH2Br – CF2 – CH2 – CH2Cl
c)
CH ≡ C – CH2Br
b)
F – CH2 – CH2 – CH2 – CH3
d)
CH3 – CH – CHF – CH2 – CH3
CH = CCl – CH3
Br
e)
CH3
Br
C
CH2
CH3
C
f)
CH3
F
C
CH3
h)
Cl
F
F
Cl
g)
F
OH
I
Cl
I
2. Draw each of the following compounds:
a) 1,2-dibromo-3-chloropropane
b) 1,4-diiodobenzene
c) 2-bromo-2-chloro-1,1,1-trifluoroethane
d) triiodomethane
e) 4,4-difluoropentan-1-ol
f) pentachlorophenol
Carboxylic Acids
1. Name the following compounds:
a)
O
CH3
c)
H
CH2 CH2
O
║
C
║
C
b)
OH
CH3 CH2
CH2 CH2
O
║
C
d)
OH
Chem 30 Organic Chemistry Workbook
CH3 – CH2 – CH2 – CH2 – CH2
7
OH
O
║
C
OH
e)
f)
F
CH2
O
║
C
CF2 CH2
O
║
C
OH
OH
2. Draw each of the following compounds:
a) propanoic acid
b) ethanoic acid
c) 2-methylbutanoic acid
d) 3,3-diethyloctanoic acid
e) 4,4-diiodo-2,2-dimethylpentanoic acid
f) 3-bromo-4-methylhexanoic acid
Esters
3. Name the following compounds:
a)
O
CH3
║
C
CH2 CH2
c)
H
O
║
C
O
b)
CH3
CH3 CH2
CH2 CH2
d)
O
CH3
O
║
C
CH3 – CH – CH2
O
CH2
O
║
C
O
CH2 – CH3
O
║
C
O
CH – CH3
CH3
e)
F
CH2
CF2 CH2
O
║
C
f)
CH3
CH3
O
CH2
CH3 – CH – CH2
CH3
CH3
4. Draw each of the following compounds:
a) methyl pentanoate
b) ethyl octanoate
c) heptyl methanoate
d) propyl 3,3-dimethlyoctanoate
e) 3-methylbutyl ethanoate
f) 2-methylpropyl methanoate
Chem 30 Organic Chemistry Workbook
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CH3
CH3
Organic Reactions
For each of the following reactions:
a. Draw the reaction.
b. Give the reaction type.
c. Name the organic reactant(s) and product(s) ***10 carbons or less.
1. Propene reacts with solid iodine.
2.
C5H12
+

O2(g)
3. 2,3-dimethyl hexane burns in the presence of oxygen gas.
4.

cat
H
C≡ C
H
+
2 Br2
5. 4,4-dimethylhept-2-ene reacts with oxygen.
6.
+ Cl2(g)
7.
+
CH3 – CH2 – CH2 – CH3
O2(g)

H2SO4

8. 3-ethyloctanoic acid reacts with ethanol.
9. Benzene reacts with liquid bromine.
OH
10.

cat
11. Cyclohexane reacts with fluorine gas.
13.

cat
12.
+
O
║
C
OH
14. 3-methylhex-1-yne
+
+

H2SO4
HO – CH3
oxygen 
Chem 30 Organic Chemistry Workbook
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CH2Cl – CH2 – CH2 – CH2 – CH3
O
║
15.
CH3 – CH2 – CH2
C
HO – CH3
OH +
16. propyne + fluorine (2 moles) 
17.

cat
CH ≡ C – CH3
+
F2

cat
18. fluoroethane
19.
+ hydroxide ion
CH3

cat
+
I2

H2SO4
20. ethanol
21.
+ pentanoic acid
CH3 – CH – CH2 – CH2 – CH2 – CH3

cat
OH

cat
22. propene + hydrogen
23.
+ O2(g) 
H – OH
+
25. benzene + iodine
26.

cat
24.
n CHCl
‗

cat

cat
CHF

H2SO4
27. butanoic acid + ethanol
Chem 30 Organic Chemistry Workbook
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
H2SO4
28.

cat
C30H62
+
C10H22
+

cat
29. chloroethane
+ fluorine
Cl
30.

cat
+
+
HCl
31. propane + oxygen 
32.
n H2NCH2

cat
+ n HO – CH2 – CH2 – OH
CH2NH2
33. propanoic acid
+

H2SO4
ethanol

cat
34.
+

cat
35. hexan-2-ol
I
36.

cat
+
+

cat
37. pent-2-ene + bromine
38.

cat
C7H16
+
C5H12

cat
39.
40.
+
n CH2
‗
CCl
decane + nonane

cat
OH
Chem 30 Organic Chemistry Workbook
11
HI
Organic Chemistry Review
1. Name the following compounds:
a)
b)
CH2 CH3
CH3
CH3
c)
d)
CH3
CH3 CH
CH
CH3
CH3
C≡ C
CH2
CH2
OH
CH3
C2H5
e)
f)
CH3
CH
CH2
CH
CH2
CH3
O
║
C
OH
CH
CH
CH
CH3
CH3
CH2
CH3
g)
CH3
CHBr
CH2
O
║
C
h)
‗
CH3 CH
CH
OH
CH2
CH3
I
Br
i)
CH3
C
Br
CH2
C
j)
CH3
F
Br
Chem 30 Organic Chemistry Workbook
Br
CH3
12
CH3
O
║
C
k)
CH3 CH2
CH2 CH2
l)
OH
m)
n)
CH3 CH2 CH2
CH3
CH2
CH2
CH
CH3
CH3
o)
p)
H
C2H5
H
H
H
H
C
C
C
C
H
H
OH H
H
CH3
q)
CH3
C
≡ C
CH
CH
CH3
CH3
CH3
CH3
r)
CH3
CH
C2H5
CH2
CH3
2. Draw the structure for the following compounds:
a) hex-3-yne
b) 1-iodo-4-propylcyclopentene
c) 1,2-dichloro-3-fluorocyclobutane
d) hexane
e) pentanoic acid
f) 3-chlorohexan-1-ol
g) 1,1-diethyl-3,3-dipropylcyclooctane
h) tetrachloroethene
i) 3-butyl-4-propylcyclopentene
j) 3-methylhexan-2-ol
k) 1,1-dibromo-3-chlorocyclohexane
l) ethyne
m) 1,2-dipropylcyclopentene
n) nonane
Chem 30 Organic Chemistry Workbook
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CH
CH3
3. Complete each of the following reactions, name the organic reactant(s) and/or
product(s), and give the reaction type.
a)
H
H
O
║
C
H
C
C
H
H
H
H
OH +
HO
b)
+
C
C
H
H
H

cat
Cl2
c)
‗
n CH2
d)
H
cat
H
C
C
H
H
e)

CHF
H

cat
OH
H
H
C
+
H

cat
F2
H
f)
+
g)
H
C
H
‗

H2SO4
H
H
H
C
C
C
H
H

cat
I2
Chem 30 Organic Chemistry Workbook
H
+
O2(g)
14

h)
H
C≡ C
+
i)
j)

acid
H
1 Cl2

H
H
C
C
H
H
H2SO4
+
O2(g)
H
O
║
C
O
H
H
C
C
H
H
H +

6. Make a chart to list the organic compounds that are polar and nonpolar.
7. You have 4 clear colourless solutions all with the same number of carbons: an alkane,
an alkene, a carboxylic acid and an alcohol. Design a procedure you could use to
correctly label all four solutions.
30-C1.1s  design a procedure to identify types of organic compounds
Chem 30 Organic Chemistry Workbook
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H – OH