CHAPTER
1
rEvIEw
K/u
Knowledge/Understanding
Knowledge
For each question, select the best answer from the four
alternatives.
1. Gasoline contains many structural isomers of octane.
Which of the following is NOT a structural isomer of
octane? (1.1) K/u
(a) 3-methylheptane
(b) 4-ethylheptane
(c) 2,2,4-trimethylpentane
(d) 2,2,3,3-tetramethylbutane
2. What is the major product of the hydration reaction
of but-1-ene? (1.2) K/u
(a) butan-1-al
(c) butan-2-al
(b) butan-1-ol
(d) butan-2-ol
3. Which of the following statements best describes an
aromatic organic compound? (1.3) K/u
(a) an aldehyde or a ketone with a distinctive odour
(b) an unsaturated compound containing a 6-carbon
ring with 6 identical bonds
(c) a compound containing a cyclic structure
(d) a compound containing a cyclic structure with
a double bond
4. Which of the following compounds is an ether?
(1.4) K/u
(a)
O
CH3CCH2CH3
O
(b)
CH3CH2CH2CH
(c)
OH
CH3CHCH3
(d) CH3CH2CH2OCH3
5. Which of the following formulas represents
propanone? (1.5) K/u
(a) CH3CHO
(b) CH3OCH3
(c) CH3COCH3
(d) CH3COOCH3
6. Which statement best describes the compound
CH3(CH2)4CH w CHCH2CH w CH(CH2)7COOH?
(1.6) K/u
(a) It is a saturated fatty acid.
(b) It is soluble in a polar solvent.
(c) It is a long-chain alcohol.
(d) It contains a carboxyl group.
72
Chapter 1 • Organic Compounds
T/I
Thinking/Investigation
C
Communication
A
Application
7. Which of the following compounds has the highest
solubility in water? (1.6) K/u
(a) CH3CH2CH w CHCH3
(b)
O
CH3CCHCH3
CH3
(c) CH3CH2CH2CH2C
OH
O
(d) CH3CH2CH2CH2CH2OH
8. Choose the statement that best describes the
compound in Figure 1. (1.6) K/u
O
CH3(CH2)7CH
CH(CH2)7C
O
OCH2
CH3(CH2)7CH
CH(CH2)7C
O
OCH
CH3(CH2)7CH
CH(CH2)7C
OCH2
Figure 1
(a) an amide
(b) a product of a saponiication reaction
(c) a saturated fatty acid
(d) a triglyceride
9. Predict which of the following compounds has the
highest boiling point. (Assume that all have similar
molecular masses.) (1.6) K/u
(a) aldehyde
(b) ketone
(c) carboxylic acid
(d) ester
10. Name the compound illustrated in Figure 2. (1.7)
H
CH3CH2
N
K/u
CH2CH2CH3
Figure 2
(a)
(b)
(c)
(d)
2-aminopentane
2-nitropentane
ethylpropylamide
N-ethylpropan-1-amine
NEL
11. Which two reactants could form the compound
illustrated in Figure 3? (1.7) K/u
Write a short answer to each question.
O
CH3
C
N
CH2CH3
CH3CHCH3
Figure 3
(a)
(b)
(c)
(d)
ethanoic acid and a secondary amine
ethanoic acid and a primary amine
ethanoic acid and a tertiary amine
methanoic acid and a secondary amine
Indicate whether each statement is true or false. If you think
the statement is false, rewrite it to make it true.
12. Unsaturated hydrocarbons must contain at least one
carbon‒carbon double or triple bond. (1.1) K/u
13. But-1-ene and but-2-ene are structural isomers of
each other (1.1, 1.2) K/u
14. Markovnikov’s rule states that, in an addition reaction
involving a hydrogen atom, the hydrogen atom will
usually bond to the carbon atom with the fewest
hydrogen atoms attached. (1.2) K/u
15. Aromatic compounds usually undergo addition
reactions. (1.3) K/u
16. A compound that is a benzene ring with a hydroxyl
group on one of the carbon atoms is called phenyl.
(1.4) K/u
17. An ester is formed from the reaction of two
alcohols. K/u
18. Aldehydes contain a carbonyl group on the terminal
carbon atom. (1.5) K/u
19. A ketone can be oxidized to produce a primary
alcohol. (1.5) K/u
20. Carboxylic acid molecules are much less polar than
the corresponding alkane molecules. (1.6)
22. Write a balanced chemical equation to represent each
of the following reactions. Use structural formulas
or line diagrams in your equations. Classify each
reaction as addition or substitution.
(1.1, 1.2, 1.3) K/u
(a) bromine reacting with pent-2-ene
(b) bromine reacting with cyclopentene
(c) bromine reacting with benzene
23. Draw a structural formula to represent each of the
following organic compounds:
(1.1, 1.3, 1.4, 1.5, 1.6) K/u C
(a) ethan-1,2-diol
(b) 1,3-dimethylbenzene
(c) cyclohexanol
(d) 1,2-dichloropropane
(e) 2,2-dichloropropane
(f) 2-methylbutanal
(g) hexan-3-one
(h) 2-ethoxypropane
(i) aminoethanoic acid
(j) 3,5-dimethylhexan-3-ol
24. List the non-alkyl functional groups in each of the
compounds represented below.
(1.1, 1.2, 1.3, 1.7) K/u
(a)
CH OH
3
CH3
O
testosterone (hormone)
O
CH3
Match each condensed chemical formula on the left with the
most appropriate term on the right.
21. (a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
NEL
CH3CH w CH2
CH3COOCH3
CH3CH2CHO
CH3CH2COOH
CH3CHOHCH3
CH3CH2CH2OH
CH3COCH3
CH3CH2OCH3
(i)
(ii)
(iii)
(iv)
(v)
(vi)
(vii)
(viii)
a ketone
an ester
propan-2-ol
propanal
an ether
propan-1-ol
propene
propanoic acid
(1.2, 1.4, 1.5, 1.6)
CH3
(b)
OH
H3C
ibuprofen (pain reliever)
(c)
NH2
CH3
amphetamine (stimulant)
K/u
Chapter 1 Review
73
25. Organic compounds are classiied by their functional
groups. For each of the compounds listed below,
identify the functional group(s), determine the type
of compound, and write the correct IUPAC name.
(1.4, 1.5, 1.6, 1.7) K/u C
(a) CH3CH2CH2OH
(b) CH3CH2COOH
(c) CH3CH2CH2CH2CH2CHO
(d) CH3CH2OCH2CH2CH3
(e) CH3NH2
(f) CH3COCH2CH2CH3
(g)
O
CH3COCH2CH2CH3
(h) CH3CH2CONHCH3
(i) CH3CHCCH2CH3
(j) H
C
O
O
OH
26. Draw structural formulas for each of the following
organic compounds. Circle the non-alkyl functional
group(s). (1.4, 1.5, 1.6, 1.7) K/u C
(a) hexan-2-one
(b) 2-methylpentanal
(c) pentane-1,3-diol
(d) buta-1,3-diene
(e) 1-propoxybutane
(f) 2-propoxybutane
(g) ethyl ethanoate
27. Draw structural formulas (or line diagrams) and
write names for the following isomers:
(1.5, 1.6, 1.7) K/u C
(a) three ketones with the molecular formula C5H10O
(b) two esters with the formula C3H6O2
(c) a primary, a secondary, and a tertiary amine, with
the formula C5H13N
understanding
28. Can CH2CF2 exhibit hydrogen bonding? Explain.
(1.1) K/u
29. If you were presented with the structural formulas
for a variety of hydrocarbons, what features of
the molecules would you look at to rank the
hydrocarbons in order of increasing boiling point?
Explain your answer. (1.1, 1.2) K/u
74
Chapter 1 • Organic Compounds
30. Draw a chemical equation to represent a reaction
that could produce each of the following types of
compounds. Use condensed structures in your
equations. Name all reactants and products.
(1.1, 1.2, 1.3) K/u
(a) alkane
(b) monohalogenated alkane
(c) dihalogenated alkane
(d) tetrahalogenated alkane
(e) halogenated benzene
(f) alkene
31. Starting with propane, list the sequence of reactions
needed to produce propanone. (1.5) K/u
32. he following compounds all have similar molecular
masses: ethanoic acid; ethanol; ethanal; ethane
Order the compounds by increasing boiling point.
Explain your decision. (1.1, 1.4, 1.5, 1.6) A
33. Explain why the following compounds do not exist:
(1.2, 1.3, 1.4, 1.5, 1.6) K/u T/I
(a) 2-chloro-2-butyne
(b) 2-methyl-2-propanone
(c) 1,1-dimethylbenzene
(d) 2-pentanal
(e) 3-hexanoic acid
(f) 5,5-dibromo-1-cyclobutanol
34. Name and draw the structural formula for
each of the following compounds: (1.2, 1.3, 1.4,
1.5, 1.6) K/u C
(a) a secondary alcohol with the formula C4H10O
(b) a tertiary alcohol with the formula C4H10O
(c) an ether with the formula C4H10O
(d) a ketone with the formula C4H8O
(e) an aromatic compound with the formula C7H8
(f) an alkene with the formula C6H10
(g) an aldehyde with the formula C4H8O
(h) a carboxylic acid with the formula C2H4O2
(i) an ester with the formula C2H4O2
35. Write a chemical equation for each of the following
reactions. Use condensed formulas. Classify each
reaction by type. (1.2, 1.4, 1.5, 1.6) K/u
(a) ethene from ethanol
(b) ethoxyethane from ethanol
(c) propanal from an alcohol
(d) a secondary pentanol from an alkene
(e) ethanoic acid from an alcohol
(f) ethyl methanoate from an acid and an alcohol
NEL
36. Copy and complete Table 1 in your notebook.
(1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7) T/I C
Table 1
Name
Condensed structure
Line diagram or structural formula
Type of compound
1-methoxybutane
methanal
1,4-dichloropent-2-ene
CH3
CH
CH2
CH
CH3
NH
CH2
CH2
CH3
CH3
propanamide
CH3CH2CH2CH2CH(OH)CH2CH3
O
3-methylhexanoic acid
OH
CH3
CH2
CH
CH2
CH
CH3
CH3
2-methylbutane
CH3CH2CH(CH3)CH2CH3
O
O
OH
methyl pentanoate
NEL
Chapter 1 Review
75
37. Predict which of the following pairs of compounds is
more soluble in water. Give reasons for your answers.
(1.3, 1.4, 1.5, 1.6) K/u T/I
(a)
COOH
and
(b) CH3COOH and CH3COOCH3
(c) ethanol and decanol
(d) 2-butanol and butanone
38. Predict which compound in each of the following
pairs has the higher boiling point. Provide a reason
for each answer. (1.4, 1.5, 1.6) K/u
(a)
CH3CH2 O CH2CH3 and CH3CH2 C CH2CH3
O
(b)
O
O
CH3CH and CH3COH
(c) CH3CH2OH and CH3CH2CH2CH2CH2OH
39. Give an example of a reaction that would yield the
following products. For each reaction, name the
organic reactant(s) and product(s). Remember to use
(O) for oxidation reactions. (1.4, 1.5, 1.6) T/I
(a) primary alcohol
(e) ketone
(b) secondary alcohol
(f) carboxylic acid
(c) tertiary alcohol
(g) ester
(d) aldehyde
40. Classify each reaction and name all the reactants and
products. (Note that the equations are not balanced.)
(1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7) K/u
light
(a) CH3CH3 1 Br2 h CH3CH2Br 1 HBr
(b) CH3CHCH2 1 Cl2 h CH3CHClCH2Cl
catalyst
(c) C6H6 1 I2 h C6H5I 1 HI
(d) CH3CH2CH2CH2Cl 1 OH2 S
CH3CH2CH2CH2OH 1 Cl2
(e) CH3CH2COOH 1 CH3OH S
C2H5COOCH3 1 H2O
S
(f) CH3CH2OH
CH2CH2 1 H2O
(g) C6H5CH3 1 O2 S CO2 1 H2O
(h) CH3CHO 1 3 O 4 S CH3COOH
(i) NH3 1 C4H9COOH S C4H9CONH2 1 H2O
(j) CH3I 1 NH3 S CH3NH2 1 HI
76
41. For each of the descriptions, write a balanced
chemical equation using condensed formulas.
(1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7) K/u
(a) a substitution reaction of propane involving
chlorine
(b) a halogenation reaction of benzene involving luorine
(c) the complete combustion of ethanol
(d) a dehydration reaction of butan-2-ol
(e) the controlled oxidation of butanal
(f) the preparation of pentan-2-one from an alcohol
(g) the preparation of hexyl ethanoate from an acid
and an alcohol
(h) the hydrolysis of methyl pentanoate
(i) the controlled oxidation of propan-1-ol
(j) an addition reaction of an alkene to produce an
alcohol
(k) a condensation reaction of an amine
Chapter 1 • Organic Compounds
Analysis and Application
42. Describe a procedure that could be used to separate
a mixture of alcohols containing methanol, ethanol,
and hexan-1-ol? Explain why this procedure would
work. (1.4) A
43. Analysis of an unknown organic compound gives
the empirical formula C5H12O. It is only slightly
soluble in water. When this compound is oxidized
in a controlled way with potassium permanganate,
KMnO4(aq), it is converted into a compound that
has the empirical formula C5H10O. his second
compound has the properties of a ketone. Based
on the information provided, write the condensed
formulas and names for all possible isomers of the
unknown compound. If possible, give reasons why
one or more of the isomers is more or less likely to be
the unknown organic compound. (1.5) C A
44. Draw a low chart outlining a procedure to synthesize
the ester ethyl ethanoate, starting from ethene.
(1.6) T/I C A
45. Create a table with the following headings: Type
of organic compound; Functional group; Physical
properties; Chemical reactions; Important uses.
Complete your table summarizing all you have
learned about the organic compounds discussed in
this chapter. (1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7) K/u C A
46. Create a graphic organizer to show how organic
compounds are related and what reactions convert one
to another. (1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7) K/u C A
NEL
Evaluation
47. Figure 4 shows the structural formulas of glucose,
propane-1,2,3-triol (glycerol), and ethane-1,2-diol
(ethylene glycol). All three compounds have a sweet
taste. (1.4) A
H
CH2OH
H
HO
O
H
C
OH
H
C
OH
H
C
OH
H
H
OH
H
H
OH
OH
H
glucose
propane-1,2,3-triol (glycerol)
HO
H
H
C
C
H
H
OH
ethane-1,2-diol (ethylene glycol)
Figure 4
(a) Predict their relative melting points and boiling
points. Give reasons for your answer.
(b) Predict the solubility of each of these compounds in
water and in gasoline. Give reasons for your answer.
(c) Ethane-1,2-diol (ethylene glycol) is toxic and is used
as antifreeze in automobile radiators. Suggest an
explanation for the toxicity of antifreeze.
(d) A hypothesis has been proposed that taste
receptors respond to functional groups in the
compounds that make up our food. Do the
structures of these three compounds support that
hypothesis? Explain.
48. Natural products are made by the cells of living
organisms. Synthetic products are made by a
laboratory process. he product may be exactly the
same compound, but a distinction is made based on
the source. For example, when bananas are dissolved
in a solvent and the lavouring extracted, the pentyl
ethanoate obtained is labelled “natural lavour.” When
pentyl ethanoate is synthesized by esteriication of
ethanoic acid and pentanol, it is labelled “artiicial
lavour.” (1.6) T/I A
(a) Are substances such as artiicial vanilla lavouring
and vanilla extracted from a vanilla bean
identical? Why or why not?
(b) In your opinion, should food companies be
required to distinguish between a “natural”
lavouring and an “artiicial” lavouring on a food
product label? Explain your position.
NEL
(c) Design a method for determining whether people
can tell the diference between synthetic vanilla and
natural vanilla and, if they can, which they prefer.
relect on your Learning
49. Write a summary of what you have learned about
organic chemistry in Chapter 1. K/u A
50. What are some typical errors made when naming
organic compounds? How can you avoid those
errors? K/u A
51. What concepts in this chapter did you struggle the
most with? Describe three ways you can help improve
your understanding of these concepts. K/u T/I
52. How would you explain to a friend why it is
important to understand organic chemistry to make
informed decisions in everyday life? A
research
WEB LINK
53. Acetylsalicylic acid (ASA), better known as Aspirin,
is a common pain reliever. Research the following
topics and summarize your indings into a short
paper, a concept map, or some other method of
communication: T/I C A
• Explore the chemical reactions associated with the
synthesis of ASA. Determine the type of reaction
that occurs, and the class of organic compounds
involved.
• Research the historical connection between willow
bark and ASA. What advantages does ASA have
over the compound extracted from willow bark?
How were these advantages achieved?
54. Organic compounds are present in a huge variety
of everyday substances. Examine the ingredient
lists for some foods, beverages, or other products
you use daily. Identify at least ive examples of
compounds whose names indicate that they
are organic compounds. Research the chemical
structures of these compounds, how they are
produced, and what their functions are in the
products you chose. Share your indings in a poster
or electronic slide show. T/I C A
55. Gasoline is a mixture of many organic compounds.
Research the structures of at least 4 of these
compounds. Find out what the “octane rating”
of gasoline means. Why do car manufacturers
recommend using fuel with diferent octane ratings
for diferent vehicles? What might happen if you
use the wrong kind? Summarize your indings into
an infomercial or poster to be displayed at a gas
station. T/I C A
Chapter 1 Review
77