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Chemistry 30:
Organic Chemistry Assignment Book
C1: I can define organic compounds and recognize the exceptions and I can identify and describe
significant organic compounds in daily life.
1. Differentiate between an organic and inorganic compound. Provide an example of each.
2. List the classes of inorganic compounds that contain carbon.
3. Identify the following compounds as organic or inorganic. Justify your choice.
a. Carbon monoxide
b. CH3CN
c. CoCO3
d. Carbon
e. CaO
f. C6H6
g. Water
h. NaCN
i. CCl4
j. CO2
C2: I can name and draw and build structural, condensed structural, line diagrams, and molecular
formulas for saturated and unsaturated aliphatic (including cyclic) and aromatic compounds.
Including: alcohols, carboxylic acids, esters, halogenated hydrocarbons
 I can identify types of compounds from their functional groups.
1. With the help of an example, explain the difference between structural, condensed
structural, and line diagrams.
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2. What is meant by the term homologous series?
3. Write the molecular formula and draw the condensed structural and line diagrams for
the following:
a. propane
b. 2-2-dimethylpentane
c. cyclobutane
d. ethylcyclopropane
4. Name the following organic compounds and draw the condensed structural formula:
a.
b.
c.
d.
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5. How does a cycloalkane differ from an alkane? Explain using general formulas.
6. Write the molecular formula and draw the condensed structural and line
diagrams for the following:
a. hept-3-ene
b. 2-methylhexene
c. 4,4-diethyloct-2-yne
d. 1,2-dipropylcyclobutene
7. Name the following organic compounds and draw the condensed structural
diagram:
a.
b.
c.
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8. Explain the difference between alkanes, alkenes, and alkynes by functional groups and
general formulas.
9. Using general formulas explain which of the following family groups are isomers of one
another. State if the each family is saturated or unsaturated.
a. alkanes
b. alkenes
c. alkynes
d. cycloalkanes
e. cycloalkenes
10. Identify all the families that the following molecular formulas belong to:
a. C2H4
b. C3H8
c. C4H6
d. C5H10
11. Differentiate between an aliphatic and aromatic hydrocarbon. Provide an example of
each and write the molecular formula for your examples.
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12. Draw the line diagrams and list the molecular formulas for the following organic
compounds:
a. ethyl benzene
b. 3-phenyloctane
c. 1-ethyl- 2-methylbenzene
13. Name the following organic compounds:
a.
b.
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c.
d.
14. Explain and illustrate the difference between cyclohexane, cyclohexene and benzene.
Explain the difference in chemical reactivity of these three compounds.
15. Draw the line diagrams for the following organic halide/halogenated hydrocarbon
compounds:
a. tetrachloromethane
b. bromoethane
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c. 2-bromopropane
d. 2-bromo-2-methylpropane
e. 3-iodo- 2,2-dimethyloct-4-ene
f.
bromocyclopropane
16. Name the following organic compounds and circle the functional group:
a.
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b.
c.
17. Provide the complete structural diagram and name the following compounds:
a. CHF2Cl
b. CH3CFCl2
c. CCl2F2
18. What is the general formula and the name of the functional group of an alcohol?
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19. Draw the line diagrams for the following organic compounds:
a. butanol
b. 3-methylbutan-2-ol
c. hexane-1,2-diol
d. 2-bromo- 3-methylheptanol
20. Name the following alcohol compounds:
a.
b.
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c.
21. Write the molecular formula and draw the structural formulas and line diagrams for the
following organic compounds:
a. octanoic acid
b. benzoic acid
c. propanoic acid
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22. Name the following organic compounds:
a.
b. HOOC-CH2-CH2-CH2-CH3
c.
23. Draw the structural formulas and line diagrams for the following organic compounds:
a. propylbutanoate
b. butylpentanoate
c. methyl ethanotae (structural diagram only)
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24. Name the following organic compounds:
a.
b.
c.
d.
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25. Identify two sets of isomers using the chemical compounds in questions 21-24.
26. Complete the following table and provide an example of each compound.
Compound
Alkane
Name and Draw the
functional group
Single bond
General Formula
R-R
CnH2n+2
Alkene
Alkyne
Benzene
Organic Halide/
Halogenated
Hydrocarbon/ Alkyl
Halide
Alcohol
Carboxylic Acid
Ester
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Example
ethane
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C3: I can define and recognize structural isomers
1. Define the term “structural isomer”.
2. Provide ALL non-cyclic structural isomers of C5H10. (There are 5)
3. Provide three structural isomers of C4H6.
4. Which one of the following compounds is an isomer of CH3CH2CH2CH2OH?
Justify your answer.
(a) CH3CH2CH2OH
(b) CH3CH(OH)CH3
(c) CH3CH2CH2CHO
(d) CH3CH2CH2CH3
(e) none of the above
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5. Draw and name three isomers of C3H6Cl2.
6. Provide and name three isomers of a five carbon alcohol.
C4: I can compare boiling points and solubility of organic compounds
 I can describe the process involves in separating organic compounds from natural mixtures
 I can design a procedure to separate a mixture of organic compounds based on boiling
point differences
1. Using the following table, explain the differences in boiling points. Write the molecular
formula of these isomers.
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2. Explain why alkanes are immiscible in water
3. Describe a solvent that they would be miscible in.
4. Why does methane have a lower boiling point than ethane?
5. Are alkenes and alkynes miscible in the following solutions. Explain your answer.
a. water
b. benzene
c. tetrachloromethane
6. Explain a physical method that is used to separate crude oil into fractions. What property
is used for this separation?
7. Explain how bitumen is extracted from oil sands. What property is used for this
extraction.
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8. Using the fractionation distillation tower below, explain why Gas is collected at the top
and Fuel Oil is collected near the bottom.
9. Explain why alcohols are miscible with water.
10. Explain which is more miscible in water, methanol or butanol.
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11. Explain why carboxylic acids are more polar than alcohols and esters.
12. Explain which is more soluble hexanoic acid or 2,3, - dimethylbutanoic acid.
C5: I can determine the saturation and interpret tests that check for the saturation of a
hydrocarbon.
1. Differentiate between a saturated and unsaturated hydrocarbon.
2. Explain what one would expect to see when bromine is added to propene and added to
propane.
3. Describe a test you would use to differentiate between cyclohexane, cyclohexene and
benzene.
4. Are esters and carboxylic acids saturated or unsaturated? Explain.
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C6: I can define, illustrate, provide examples, and predict products for of addition, substitution,
elimination, esterification, and combustion reactions.
1. Explain the difference between an addition and substitution reaction.
2. Identify possible product(s)/ reactant(s) and the type of reaction that occurred for the
following: Draw the structures to help you visualize the reactions.
a. propane + chlorine 
b. ______ + _______  ethanol
c. 2-chlorohexane + hydrogen iodide 
d. benzene + iodine 
e. ethyne + excess hydrogen 
f.
prop-2-ene + bromine 
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3. What reaction type produces an alcohol and what reactants are needed?
4. What is the relationship between an elimination reaction and an addition reaction?
5. Illustrate the following reactions and identify the type of reaction that is taking place:
a. The formation of hexan-2-ol from an alkene.
b. The reaction between 2-bromobutane and iodine gas.
c. A reaction that forms potassium bromide, water and but-2-ene.
d. The reaction between water and cyclohexene.
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e. The reaction between benzene and iodine gas.
f.
A reaction that forms prop-2-ene and water.
6. What two reactants are necessary in order for an esterification reaction to occur, and
what conditions are necessary?
7. What inorganic by-product is always formed in an esterification reaction?
8. Predict the name of the organic compound formed , its by-product, or reactants for the
following reactions:
a. methanol + butanoic acid 
b. _______________ + methanoic acid  ethylmethanoate +
c. pentanol + __________________  pentylethanoate +
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9. Name the following esters, and the acids and alcohols from which they were prepared:
a. CH3CH2COOCH2CH3
b. CH3CH2CH2COOCH3
c. HCOOCH2CH2CH2CH3
d. CH3COOCH2CH2CH3
10. Explain the difference between a complete and incomplete combustion reaction.
11. Write the balanced chemical equations for the following reactions:
a. The complete combustion of 3-methylhexane
b. The incomplete combustion of benzene
c. The complete combustion of cyclohexane
d. The incomplete combustion of octane.
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12. Explain how to recognize the following reactions:
a. Addition
b. Substitution
c. Elimination
d. Esterification
e. Complete combustion
f.
Incomplete combustion
C7: I can define, illustrate and provide examples of monomers, polymers, and polymerization
1.
Draw the polymers that are created from the following monomer subunits:
a. but-1-ene
b. 1-chloro-1,2,2-trifluroethene
c. propyne
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2. Draw and name the monomer that formed the following polymers
a.
b.
c.
3. What functional group(s) must be present in a monomer that undergoes an addition
polymerization reaction?
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4. Explain the differences between addition polymerization reactions and condensation
polymerization reactions?
5. Explain why the below is a condensation polymerization reaction. List the families that
the polymer belongs to.
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