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Organic Review and Practice Answers
Name or draw the following compounds:
Chemical structure
1
IUPAC Name
2-chlorobutane
Cl
H3C
CH2
CH CH3
CH3
2
CH2
H3C
CH
CH2
HC
3,5-dimethylheptane
CH3
CH2
CH3
3
4
Br
Br
H3C CH
CH2
Cl
CH
CH
C
CH3
Cl
CH3
CH3
H3C CH CH2 C CH2
CH3
CH3
4,6-dibromo-2,2-dichloro-3-methylheptane
2,4,4-trimethylhexane
CH3
CH3
CH2
5
Cl
HC CH2
CH
CH2
CH
CH3
2,3,7-trichloro-5-ethyloctane
Cl
Cl CH
CH3
6
Cl
Cl C CH2
Cl
Cl
Cl
C CH2
C CH3
Cl
Cl
1,1,1,3,3,5,5-heptachlorohexane
CH3
7
CH2
H3C
C
Br
CH2
CH
CH3
2-bromo-4,4-dimethylhexane
CH3
8
Br
H3C CH2
C CH2
CH3
3-bromo-3-chloropentane
Cl
Cl
9
CH3
2,3-dichloropentane
CH CH CH2 CH3
Cl
CH3
10
CH3 CH CH CH2 CH2 CH2 CH3
3-bromo-2-methylheptane
Br
1
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CH3
Cl
1,2-dichloropropene
C C
11
H
Cl
(trans geometric isomer)
Cl
12
CH3 CH CH2
Cl
NH2
CH2 C CH CH CH3
NH2
4,4-diamino-2,3,6-trichlorooctane
Cl
Cl Cl
13
CH3 C
2,2,3,3,4-pentachloropentane
C
CH CH3
Cl Cl Cl
CH3
14
H3C C
CH2
Br
Br
C
C
2,3-dibromo-5,5-dimethyl-2-hexene
CH3
CH3
CH3
Cl
15
CH
HC CH2
5-chloro-3-methyl-2-hexene
C CH3
CH3
16
H3C
CH3
CH3
C
C
CH3
CH3
C
C
CH2
Cl
Cl
C
C
CH2
Cl
17
H3C
C
CH3
3,4-dichloro-6,6,7,7-tetramethyl-3-octene
4,4-dichloro-2-pentyne
CH3
Cl
18
HC
C
CH3
19
Br
Br
CH
CH
CH2 C C
3,4-dibromo-1-hexyne
CH2
CH3
CH CH2 CH3
5-amino-3-heptyne
NH2
Aromatic Hydrocarbons
Chemical structure
IUPAC Name
Cl
1,2,4-trichlorobenzene
1
Cl
Cl
2
2,3,4,5-tetrachlorophenol
2
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Cl
Cl
OH
Cl
Cl
3
Cl
Br
2,3-dibromo-4-chloro-1-nitrobenzene
Br
NO2
4
Consider the following structure
representing a benzene molecule
substituted with a number of different
groups. (A, B, C, D, E and F
State whether the following pairs of
groups are ortho, meta or para to each
other.
a)
b)
c)
d)
e)
A
F
B
E
C
D
B&D
F&C
E&F
A&C
B&E
meta
para
ortho
meta
pata
f) F & B meta
g) B & C ortho
h) F & A ortho
i) E & C meta
Isomers – Same Formula / Different Arrangement
1. Examine each of the following pairs of structures and decide if the two are identical,
isomers or different compounds.
a.
b.
Chemical structure
Chemical structure
Identical / isomers/
different formula
H3C
H3 C
Different
Formulae
CH2
OH
CH2
H2C
H3C
CH
CH2
OH
CH2
Isomers
(C3H6)
CH2
CH2
c.
d.
O
O
H3C
C
H
H3C
CH2
NH2
H
Identical
C
CH3
H
H3C
N
O
Isomers
(C2H7N)
CH3
O
Identical
e.
H3 C
CH2
C
O
H
H
O
C
O
f.
H
C
CH2
CH3
O
O
CH2
CH3
H3 C
CH2
C
O
H
Isomers
(C3H6O3)
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O
O
g.
H
h.
C O
CH2
CH2
OH
HO
CH2
O
CH2
C
OH
O
H3C C CH2CH3
H3C CH2
O
Identical
C CH3
O
Isomers
(C3H7NO)
i.
H3C
NH
C
CH3
H3C CH2
Isomers
(C3H6O3)
C
NH2
Alcohols, Aldehydes, Ketones and Carboxylic Acids
Name or draw the following compounds:
Chemical structure
1
H3C
Cl
Cl
C
CH
CH
Cl
2
Cl
H3C
CH
IUPAC Name
3,4,4-trichloro-2-pentanol
CH3
OH
H2 C
CH2
CH2
C
CH2
CH3
OH
4,5-dichloro-4-ethyl-1-hexanol
Cl
NH2
3
2,2-diamino propanol
CH3 C CH2 OH
NH2
3,4-dichloropentanal
(* since the aldehydes group always at
carbon 1, no number is needed)
H
4
H3C
5
6
CH
CH
Cl
Cl
CH3
CH2
C
O
2,4-dimethylpentanal
CH3
H
H3C
CH
CH2
CH
C
H3C
CH2
CH2
C
CH2
O
CH3
3-hexanone (a ketone)
O
CH3
7
CH3 C
Cl
8
H3 C
CH2
CH2
COOH
C
O
2-chloro-2-methyl propanal
H
butanoic acid (a carboxylic acid)
(the carbon bonded to 2 O’s is C1)
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H3 C
9
COOH
10
H COOH
11
H3C CH2
ethanoic acid (aka acetic acid)
methanoic acid (aka formic acid)
COOH
CH
CH
CH2
2-ethyl-3-methylpentanoic acid
(carboxylic acid group is C1)
CH3
CH3
Cl
Cl
12
C C
CH3
cis-4,5-dichloro-4-heptenoic acid
O
CH3 CH2 C
CH2
OH
For each of the following, name the functional group and state the type of
organic compound
carbonyl; aldehyde
O
(ethanal)
1
H3C
C
H
carboxyl (combines carbonyl +
hydroxyl); carboxylic acid
(ethanoic acid)
hydroxyl; primary alcohol
(i.e. hydroxyl on C1)
(1-propanol)
O
2
3
H3C
C
H2C
CH2
OH
CH3
OH
4
H3C
C
CH2
carbonyl; ketone
(butanone)
CH3
O
H
5
C
CH2
carbonyl; aldehyde
(propanal)
CH3
O
carbonyl; ketone
(propanone; aka acetone)
CH3
6
H3 C
C
O
Types of organic reactions
1. Identify the type of organic reaction represented by each of the following equations:
a.
H
H
H
C
C
H
H
H
+
H
H
C
C
H
H
heat
Br
Br
H
Br
+
HBr
substitution (replace H with Br on an alkane)
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H
b.
H
H
C
C
H
H
+
C
H2O
H
H
H
H
H
C
C
C
H
OH
H
H
addition (hydration) (Note Markovnikov’s Rule)
c. double addition (alkyne + hydrogen halide  alkylhalide)
Cl
H3C
C
+ 2HCl
CH
H3C
C
CH3
Cl
d. addition (halogenation of an alkene)
H
H
C
H
C
C
C
H
Br
H
+
H
C
H
H
H
C
Br
Br
H
C
H
C
H
C
C
H
C
H
Br
H
C
H
H
H
H
H
e. Elimination OH
(acid-catalyzed dehydration; second product is water)
CH2
CH2 HC
conc. H2SO4
H2C
f.
H2C
CH2
CH2
CH
CH
CH2
CH2
CH2
Mild oxidation (aldehyde  carboxylic acid)
H
H
C
H
K2Cr2O7
C
H
C
H
H
g.
H
O
H
H
H
C
C
C
H
H
H
O
C
H
H
+
2 Cl
OH

Cl
H
H
Cl
Cl
C
C
C
H
H
H
H
+
2
HCl
substitution with two mol Cl2
2. Write the equation for the addition reaction involving propene and bromine.
Br
CH3 CH CH2
+
CH3 CH CH2
Br2
Br
3. Complete the following equations by writing the structures of the products that form.
If no reaction occurs, write “no reaction”.
a.
H3C
CH
CH2
+

H2O
acid catalyst
(2-propanol)
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b.
H3C
CH
CH

+
CH3
H2O
acid catalyst
(2-butanol)
c.
1,3-dibromobenzene (also 1,2- and 1,4-)
Br
+
Br2
(3 possible products but ortho isomer is favoured)
d
H3C
CH2 CH2 CH3
e.
OH
+ HO
2
no reaction
conc. H2SO4
cyclopentene
+
H2O
f.
O
C
H3C
+
CH3
K2Cr2O7
no reaction (ketones do not undergo mild oxidization )
g.
CH2
H3C
O
CH
+
+
K2Cr2O7
H2SO4
propanoic acid
h.
CH
H3C
CH3
+H
, pressure
2
CH
Pt catalyst
butane (addition ; hydrogenation)
4. a) Write the equation for the complete oxidation (combustion) of 2-butanol.
C4H9OH + 6O2  4 CO2 + 5 H2O
b) Write the equation for the mild oxidation of 2-butanol with KMnO4.
OH
CH3CHCH2CH3
KMnO4
O
CH3CCH2CH3
5. Write the equation for the addition of hydrochloric acid to ethene. What is the name
of the product formed?
CH2 CH2
+
HCl
CH3 CH2Cl
chloroethane
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6. Predict the product formed when HCl is reacted with each of the following
compounds. Use Markovnikov’s Rule to predict the product.
a.
H3C
CH
H3C
H3C
c.
H3C
2-chloropropane
CH3
C
b.
CH2
C
H
C
2-chloro-2-methylbutane
CH
2,2-dichloropropane
7. Describe the chemical test that could be carried out to distinguish between hexane
and hexene.
This is one of several possible answers.
Alkenes such as hexene will react with bromine at room temperature in an addition
reaction, while alkanes require heat or UV light to catalyze a substitution reaction. .
Simply determine if the hydrocarbon makes a brown bromine solution turn clear at
room temperature
–
this is a positive test for alkenes. Alkanes DO NOT
react with bromine at room temperature.
8. Write the equation for the substitution reaction involving one molecule of each of
ethane and bromine.
ethane + bromine  bromoethane + hydrogen bromide
9. What is the structure of the missing organic reactant in each of the following:
cyclohexene
+
, pressure
H2
Pt Catalyst
10. Write the structure of the carboxylic acid that forms when the following aldehyde is
oxidized:
CH2
H3C
O
CH3CH2COOH
CH
propanoic acid
11. Which of these two compounds is easily oxidized by KMnO4? Write the structure of
the organic product of the oxidation.
O
a.
H3C
CH3
no reaction
O
b. H3C CH2 C H
forms propanoic acid
12. What are the products of the mild oxidation of
a. 1-propanol  propanal  propanoic acid
b. 2-propanol  propanone
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Organic Compounds and Functional groups
1. Name the type of organic compound each of the following would be classified as:
a. Propanol
(alcohol)
b. Aminoethane
(amine)
c. Butanone
(ketone)
d. Methoxymethane
(ether)
e. Ethanal
(alhehyde)
O
H
H
H
H
f.
O
C
C
H
h H C C
H
C
C
.
H
H
H
H
.
H
.
aldehyde – ethanal
ketone - butanone
g.
H
.
H
H
C
C
H
H
O
H
i
C
H
C
O
H
OH
carboxylic acid – propanoic acid
H
H
C
C
H
H
H
ether - methoxyethane
2. Write the name for each of the following:
H
a.
H
C
f.
O
C
H
H
H
ethanal
b.
H
H
O
H
H
C
C
C
C
H
H
H
g.
H
H
H
H
OH
H
C
C
C
H
H
H
H
H
C
H
H
H
O
O
C C
h.
C
H
H
C
C
H
H
H
H
H
H
H
C
C
C
C
H
H
H
H
OH
1-butanol
i.
H
H
N
H
2-propanol
e.
H
N
H H
methanal
(aka formaldehyde)
H
C
H
3-pentanone
C
d.
C
H H
H
O
H
H
aminoethane
butanone
c.
H
H
H
H
C
C
C
H
H
H
H
1-aminopropane
H
H
H
H
C
C
C
C
H
H
H
H
1-methoxybutane
j.
H
H
H
H
H
C
C
C
H
H
H
O
C
OH
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SCH4U
butanoic acid
3. Name the type of organic compound each of the following would be classified as:
O
a.
g.
H3C
CH2
C
O
CH2
h.
C
O
H3C
ester (ethyl propanoate)
H3C CH2
CH2
H
O
CH3
b.
c.
C
aldehyde (propanal)
aromatic
H3C
CH2
OH
CH3
keton (propanone)
i.
o
1 alcohol (1-propanol)
cyclic alkane (cyclopentane)
O
H3C
C
C
CH3
d.
e.
H3C
CH2
O
CH2
j.
carboxylic acid
(methanoic acid)
l.
H2C
H
alkyne( 2-butyne)
CH3
ether (ethoxyethane)
4. Draw the structural formula for:
a.
b.
c.
d.
e.
f.
g.
h.
Methoxymethane
1-pentanol
1-aminobutane
propanal
2-propanol
2-methyl-4-octanol
2-methoxypropane
propyl ethanoate
C
CH
OH
CH2
CH3
alkene (1-butene)
a) CH3 O CH3
b) CH3CH2CH2CH2CH2OH
CH3CHCH2CHCH2CH2CH2CH3
c) CH3CH2CH2CH2NH2
d)
OH
f)
CH3
O
CH3 CH2 C
2
g) CH3 CH CH3
H
O CH3
e) CH3CH2CH3
O
h)
OH
CH3CH2CH2 O C CH3
5. Name the type of organic compound each of the following would be classified as:
O
a.
H3C C
HO
CH3
b.
CH2
CH
C
C
CH2
CH3
Propanoic acid
ketone (2-pentanone)
H3C
O
k.
CH2 CH2 CH3
l.
CH3
CH3
alkene (2-methyl-2-pentene)
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aromatic (methylbenzene)
c.
H3C
O
CH2
O
o.
CH3
ether (methoxyethane)
H3C
CH
C
CH
CH3
CH3
CH3
ketone
(2,4-dimethyl-3-petnanone)
CH3
d.
HO
C
p.
H3C
CH2
CH2
CH2
COOH
carboxylic acid (pentanoic acid)
CH3
CH3
3o alcohol (2-methyl-2-propanol)
O
g.
H
C
CH2
H3C CH2
CH3
O
CH2
CH2
O
H3C
O
C
CH
CH3
C
H
H3C CH2
O
C
CH3
ether (ethoxy ethanoate)
s.
CH3
O
r.
aldehyde (pentanal)
i.
CH2
2 alcohol (2-hexanol)
h.
CH2
CH2
o
aldehyde (propanal)
H3C
OH
q.
H3C
CH2
OH
o
1 alcohol (ethanol)
ether (methoxy ethanoate)
11