Functional Groups
1. Draw the following alcohols
a)
b)
c)
d)
e)
f)
g)
h)
i)
heptan-2-ol
N-propylpentanamide
1-methoxy-4-chlorohexane
3-methyloctanal
2,2-dimethylhexan-3-one
3,5-dimethylheptanoic acid
propyl 3-ethylhexanoate
propan-1,2-diamine
N-methyl-3-methylhexanamide
2. Name the following alcohols
H3C
O
CH
CH2
a) H3C
CH2
CH2
H3C
OH
CH2
HC
CH3
CH2 HC
CH3
b)
H3C
CH3
O
CH2
OH
H3C
CH
c) HO
C
CH2
CH2
C
CH2
O
e)
C
CH2
CH
N
CH3
CH3
CH3
3. Explain why the propane that is used as a fuel in a BBQ is gas at room temperature, but 2-propanol used as
rubbing alcohol is a liquid at room temperature.
4. Arrange the following compounds in increasing order of predicted solubility, and give reasons for your answers:
butanal, butane, butanol.
5. The labels have fallen off three bottles. Bottle A contains a gas, bottle B contains a liquid, and bottle C contains
a solid. The labels indicate that the compounds have the same number of carbon atoms, one being an alkane, one
an alcohol, and the other a carboxylic acid. Suggest the identity of the contents of each bottle, and give reasons
for your explanation.
6. In what way is the functional group of an ester different from that of a carboxylic acid? How does this
difference account for any differences in properties?
7. Explain why amines generally have lower boiling points than alcohols of comparable molar mass.
8. Which functional groups can you expect to turn litmus paper red? Blue?
9. Which functional groups would form hydrogen bonds with neighboring molecules?
10. Draw as many structural isomers with the formula C4H10O as possible.
Alkanes
1. Give the correct IUPAC name for the following alkanes:
2. Identify any errors in the name of each hydrocarbon.
a) 2,2,3-dimethylbutane
b) 2,4-diethyloctane
c) 3-methyl-4,5-diethyl-nonane
3. Identify the three properties of carbon that allow it to form such a great variety of compounds. (Why are
there
so many more organic compounds than inorganic compounds?)
4. Indicate whether each of the following situations meet or do not meet the bonding requirements for
carbon
atoms.
a) Two single bonds and a double bond.
b) A single bond and two double bonds.
c) Three single bonds and a triple bond.
d) A double bond and a triple bond.
e) Two double bonds.
5. What is the difference between a hydrocarbon and a hydrocarbon derivative?
6. What is the difference between saturated and unsaturated hydrocarbons?
7. What is the structural feature present in an unsaturated hydrocarbon that is not present in a saturated
hydrocarbon?
8. Compare the shape around a single-bonded carbon atom with the shape around a double-bonded and
triplebonded
carbon atom. Use diagrams to illustrate your answer.
9. Draw the indicated type of formula for the following alkanes.
a) The expanded structural formula for a straight-chain alkane with the formula C5H12.
b) The expanded structural formula for CH3― (CH2)6― CH3.
c) The condensed structural formula, using parentheses for the ― (CH2)― groups, for the straight-chain
alkane C10H22.
d) The molecular formula for the alkane CH3― (CH2)6― CH3.
10. What general condition must be met before two compounds can be isomers?
11. Explain why two alkanes with the molecular formulas C5H12 and C6H14 could not be isomers.
12. The molecular formula of C6H14 has five isomers. Draw the complete, condensed, and line structural
diagrams
for each of these isomers.
a. C5H12 (4 isomers)
b. C7H16 (9 isomers)
Alkenes
1. Name each hydrocarbon.
2. Name each hydrocarbon.
3. Draw a condensed structural diagram for each compound.
a. 2-butene
b. 3-ethyl-2,3,4,4-tetramethyl-1-pentene
c. 2-methyl-1-butene
d. 3-ethyl-2-pentene
e. 2-methyl-2-heptene
f. 3,4-dimethyl-2-pentene
4. You have seen that alkanes, such as C5H12, can have isomers. Draw condensed structural formulas for isomers of
C4H8. Then name the isomers.
5. Draw and name the cis-trans isomers for C5H10. 6. Why can 1-butene not have cis-trans isomers? Use structural
diagram to explain.
7. Like other isomers, two cis-trans isomers have the same atomic weight. They also yield the same elements when
decomposed. How might you distinguish between two such isomers in the lab?
8. C6H12 has four possible pairs of cis-trans isomers. Draw and name all four pairs.
Alkynes
1. Name each alkyne.
2. Draw structural diagram for:
Reactions of Alkenes and Alkynes
1. For each reaction, draw the products and name the reaction type.
a) CH3 ― CH = CH ― CH3 + H2 →
d) CH3 ― CH = CH ― CH2 ― CH3 + Br2 →
b) CH3 ― CH2 ― CH = CH ― CH2 ― CH3 + Cl2→
e) CH2 = CH2 + n CH2 = CH2 →
c) CH2 = CH2 + H2O →
f)
CH3 ― CH = CH ― CH2 + HCl →
2. A number of organic reactions are given below. Draw the structural formulas for each and state the
type of reaction. Complete and balance the reactions. Finally, name the products.
a) propene + hydrogen 
b) 2-pentene + bromine 
c) ethene + water 
d) propyne + (2 mol) iodine 
e) propane + bromine 
f) 2-butene + hydrobromic acid 
g) 3-hexyne + (2 mol) chlorine 
Aromatic Hydrocarbon(Benzene)
1) Give an acceptable name for the following compounds.
Cl
CH CH2
OH
Cl
OH
Cl
Cl
NO2
CH(CH3)2
Br
Cl
CH2OCH2CH3
CH2CH2CH2C
Cl
CH
N
2) Draw the structure of the following compounds.
a. 2,4-dimethylphenol
f. 4-nitroaniline
b. 4-chloroaniline
g. o-xylene
c. p-toluenesulfonic acid
h. benzoic acid
d. benzyl amine
i. p-divinylbenzene
e. benzyl ethyl ether
j. naphthalene