Chapter 22-Organic Chemistry
Chapter 22 key concepts:
 Naming/Drawing
alkanes/cycloalkanes
 Naming/Drawing alkenes
 Naming/Drawing alkynes
 Naming/Drawing aromatics
 Structural Isomers






Geometric Isomers (cis/trans)
Cracking Reactions
Reforming Reactions
Fractional Distillation
Naming/Drawing
Organic Halides
1. Name the following Organic Compounds:
a)
c)
b)
e)
d)
f)
g)
h)
i)
2. Draw the following organic compounds:
a. 2,4,4-trimethyl-1-pentene
b. 1,2,3-triphenylheptane
c. 1,3-dibromo-2-chloro-5-methylcylcohexane
d. 3,3-difluoro-1,4-pentadiene
e. 4–ethyl–2,6–dimethyl–2–heptene.
f. 1,1-dichlorobenzene
3. Based on what you know about the ability of a carbon-carbon double bond to rotate, do
these two structures represent isomers, or are they just the same molecule?
Cl
Cl
Cl
H
H
C C
H
H
C C
Cl
4. Label this alkene as the “cis” or “trans” isomer. Draw the other isomer beside it.
CH3
H
C
H
CH3
CH2CH3
C
C
CH2CH3
H
C
H
5. Can this alkene exist as cis and trans isomers? To find out, try to draw and label the
two isomers.
CH3
H
C C
CH3
H
6. Draw the reactants and draw and name the possible products for the following
reactions(if there are more then one possible set of products name at least two):
a. Pentane is cracked
b. Heptane is cracked
c. Propane and butane undergo a reforming reaction
d. Benzene burns in air
7.
a)
b)
c)
d)
Draw and classify the following reactions:
Nonane → pentane + butane
Heptane + Oxygen → Carbon dioxide and water
Methane + Ethane → propane
Octane → ethane + hexane
8. Explain why smaller hydrocarbons are distilled off higher in the fractionating
column then the larger ones.
Chapter 23-Organic Chemistry continued
Chapter 23- Key concepts
 Naming/Drawing alcohols
 Naming/Drawing aldehydes
 Naming/Drawing ketones
 Naming/Drawing carboxylic acids
 Naming/Drawing esters
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

Addition reactions
Substitution reactions
Esterfication reactions
1. Name and classify the following organic compounds:
a.
b.
CH3CH2CHCHCH2CH2 OH
c.
Cl CH3
d.
e.
g.
h.
f.
i.
j.
k.
2. Draw the following Organic compounds:
a. 2-bromopentanoic acid
b. 1, 3-pentanediol
c. 10-chloro-1-decanol
d. 2,3,4,5-tetrachlorohexanal
e. 2-chloro-6-methylheptanoic acid
f. ethyl 3,4-dimethylhexanoate
g. 4-methylpentyl-3-chlorohexanoate
h. 2-bromo-6-phenyl-3cyclopropyl-7-nonanone
l.
3. If you react 3- heptene with hydrogen bromide, which of the following is a possible
product?
a. 2-bromoheptane
b. 3-bromoheptene
c. 4-bromoheptane
d. 3,4-dibromoheptane
4. Which of the following reactions could be used to synthesize
1,2-dibromopropane?
5. Draw and name all possible products for this reaction (there are two):
(It will be helpful to first draw the full structural formula of the alkane.)
CH3CH2CH3 + Br2
 ?
6. Draw and name all possible products for these reactions and classify the reaction.
a.
CH3
CH2CH3
C
+
C
CH3
I2
CH2CH2CH3
b.
Br
H
+
C C
CH3
HCl
H
c. Benzene + Iodine →
d. 3,4-dimethyldecanoic acid + 1-propanol →
e. 2,4-dichlorohexanoic acid + 3-methyl-1-pentanol →
f. cyclohexane + chlorine →
g. 4-methyl-2-hexyne + excess fluorine →
h. chlorobenzene + bromine →

7. Determine the starting compound (reactant) that would produce the following product:
Cl Cl
+
2 Cl2
CHCH
Cl Cl
For further review, check out these websites:
http://herh.ccrsb.ca/staff/FarrellL/downloads11.htm#org
http://vuchemistry.com/resources/Organic+Review+Worksheet+Resource.doc