Organic-Practice
Note: this sample test does not reflect length, weight and necessarily every topic and type of
question that will be on the unit test. It should not be your only study tool, but rather used in
conjunction with class notes, textbook and other resources.
Multiple Choice
Identify the letter of the choice that best completes the statement or answers the question.
____
1. Which of the following is an alcohol?
a. NaOH
b.
d.
e.
c.
____
____
____
____
2. How many actual double bonds does the benzene ring possess?
a. 4
d. 1
b. 3
e. 0
c. 2
3.
What is the correct name for the above compound?
a. 2-methyl-3-butanol
d. 3-methyl-2-butanol
b. 2-pentanol
e. none of these
c. isobutanol
4. What results when a secondary alcohol is oxidized?
a. a ketone
d. an acid
b. an amine
e. no reaction
c. an aldehyde
5.
The correct name for compound above is which of the following?
a. chloropropylbenzene
c. 1-chloro-3-phenyl-3-propene
b. 3-phenyl-1-choloropropyne
d. 3-chloro-1-phenyl-1-propene
____
____
6.
The correct name for the compound given above is which of the following?
a. 1-amino-3-ethoxyhexane
c. 1-amino-3-methoxycyclohexane
b. 1-methoxy-3-amidecyclohexane
d. 1-amino-3-methoxyhexane
7. The reaction of CH3CH=CH-CH=CH2 with excess bromine gives chiefly
a. 1,2-dibromo-3-pentene
2
____
____
b. 3,4-dibromo-1-pentene
c. 1,4-dibromo-2-pentene
d. a mixture of the above three compounds
e. none of the above three compounds
8. The nitration of benzene with nitric acid is best done in which of the following?
a. water
d. ethanol
b. sulfuric acid
e. carbon tetrachloride
c. sodium hydroxide
9. Which of the following is the correct IUPAC name for the compound below?
a. 4-phenyl-6-cyclobutylhexanoic acid
b. 3-phenyl-6-cyclobutylhexanoic acid
c. 3-cyclohexyl-6-cyclobutylhexanoic acid
d. 4-cyclohexyl-5-cyclobutylpentanoic acid
____ 10. The primary product of the following reaction is which of the following?
a.
c.
b.
d.
____ 11. Which group of these compounds tends to be the most reactive?
a. alkanes
c. alkynes
b. alkenes
d. aromatics
____ 12. Name the following compound:
a. 2-chloro-6-ethyl-3-methyloctane
d. 2-chloro-6-propyl-3-methyloctane
b. 2-chloro-6-ethyl-3-methyldecane
e. 2-chloro-6-ethyl-3-methylheptane
c. 2-chloro-6-methyl-3-ethyloctane
____ 13. The alcohol below is classified as which of the following?
3
a. primary alcohol
c. tertiary alcohol
b. secondary alcohol
d. aromatic alcohol
____ 14. Select the compound with the highest boiling point at standard pressure.
a.
d.
b.
e.
c.
Unknown
B.P
Red
Litmus
Paper
Blue
Litmus
Paper
Odour
Solubility in
H2O
I
48°C
Turns blue
No reaction
Fishy smell
Yes
Weak
reaction
II
161°C
No reaction
Slightly red
None
Yes
Vigorous
reaction
III
38°C
No reaction
No reaction
None
No
Weak
reaction
IV
164°C
No reaction
Turns red
Unpleasant,
rancid odour
Yes
No reaction
Reaction
with an
oxidizer
____ 15. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, she
produces the above chart. Unknown I is most likely which of the following?
a.
d.
b.
e.
c.
____ 16. A forensic scientist is trying to identify the functional groups in some unknowns. After several tests, she
produces the above chart. Unknown IV is most likely which of the following?
a.
d.
b.
e.
4
c.
____ 17.
Which of the following is an oxidation product of the above compound?
a.
c.
b.
d.
____ 18. What is the correct IUPAC name for compound below?
a. 2-ethyl-5-hexanone
d. 5-methyl-2-heptanone
b. 5-ethyl-2-hexanone
e. 2-heptanone
c. 3-methyl-6-heptanone
____ 19. Which of following chlorine compounds has had a negative influence on Earth's ozone layer?
a. chlorofluorocarbons (CFC's)
b. hexachlorobenzene
c. dichlorodiphenyltrichloroethane (DDT)
d. tetrachloromethane (carbon 'tet')
____ 20. The compound shown below can be prepared by which of the following?
a. substitution of benzene with chlorobenzene
b. condensation of hydroxybenzene (phenol)
c. hydrogenation of diphenylmethanone
d. oxidation of diphenylmethane
____ 21. A chemist wishes to identify an unknown alkene. She does the following series of reactions with the unknown
alkene:
i. hydration
ii. oxidation
producing the 1-cyclohexyl-2-propane. The unknown alkene's structure is which of the following?
a.
c.
5
b.
d.
____ 22. Which of the following trivial or common names do not match the IUPAC names?
a. 1,2-ethanediol and ethyleneglycol
c. hydroxybenzene and phenol
b. propanal and formaldehyde
d. ethyne and acetylene
____ 23. The proper term used to describe a polymer made by combining large numbers of identical monomers is
which of the following?
a. natural polymer
d. condensation polymer
b. addition polymer
e. thermoplastic polymer
c. thermoset polymer
____ 24. Which one of the following functional group is not present in carbohydrates?
a. ketone
d. ether
b. alcohol
e. aldehyde
c. amide
____ 25. Which group is the side chain of the amino acid show below?
O
NH 2
HO
a. H3C
O
c.
C
HO
b.
d.
NH2
CH
C
H3C
Name of
Compound
H3C
CH3
M.P. (°C)
CH3
Moles of H2 Needed to Moles of CO2 Produced from
Reduce 1 mol of
combustion of 1 mol of
Compound
Compound
lauric acid
44

12.0
myristic acid
59

14.0
palmitic acid
64

16.0
stearic acid
70

18.0
oleic acid
4
1.0
18.0
linolenic acid-A
-5
3.0
18.0
linolenic acid-B
-11
3.0
18.0
____ 26. The table above shows the results of a chemist's analysis of various fatty acids. What would be the best
explanation why oleic acid has a higher melting point than linolenic acid-B?
a. oleic acid has more hydrogen bonding than linolenic acid-B
b. oleic acid has more trans double bonds than linolenic acid-B
6
c. oleic acid has a longer carbon chain than linolenic acid-B
d. oleic acid has fewer cis double bonds than linolenic acid-B
____ 27. The table below shows the results of a chemist's analysis of various fatty acids. What is the best explanation
to describe the difference in boiling points between linolenic acid-A and linolenic acid-B?
a. Acid-A has greater surface area than acid-B
b. Acid-A contains trans double bonds, acid-B contains cis double bonds
c. Acid-A has stronger hydrogen bonds than acid-B
d. Acid-A does not 'stack' as well as acid-B
____ 28. What is the monomer for the polymer Kel-F shown below?
a.
c.
b.
d.
____ 29. Which of the following compounds can produce an addition polymer?
a.
c.
b.
d.
____ 30. Mutations in DNA are not the result of the following?
a. nitrites
c. X-rays
b. UV radiation
d. changes in pH
Short Answer
31. Benzoic acid is used as a preservative in maraschino cherries. High levels are added to prevent spoilage.
Sketch the structure of benzoic acid and comment on why its inclusion in food should be a concern for
consumers.
32. Use the data given below to construct a graph of boiling points of straight-chain alkanes versus the number of
carbon atoms. Explain the shape of the graph produced. Predict the boiling point of decane.
Name
Boiling Point (ºC)
Methane
-161.0
Ethane
-88.5
Propane
-42.0
7
Butane
0.5
Pentane
36.0
Hexane
68.7
Heptane
98.5
Octane
125.6
Nonane
150.7
Decane
?
33. As a chemical supplier, list the what points should be on a general warning label for containers of diethylether
you are shipping to a customer. Include the condensed formula of the compound. Specific values for physical
properties are not required.
34. Our drinking water is fluorinated with fluoroganic compounds to help prevent tooth decay. Why is the
ingestion of fluorine not as great of a concern as the intake of chlorine in our water?
35. During the prohibition era in the United States, it was illegal to produce and sell alcoholic beverages. Many
individuals and organizations went around the law to produce their own products. What were some of the
difficulties faced during production by these 'moonshiners'?
36. When a car wax is manufactured, several properties are desired in order to protect a vehicle's finish. Describe
the qualities a good car wax should have.
37. A world shortage of ethylene glycol in the late 1990s caused many Canadian companies to manufacture their
own. Using the readily available petrochemical ethane, describe a possible synthesis whereby this was done.
38. Aspartame, marketed under the trade name Nutra-Sweet, has the following structure:
It is made from 2 compounds known as amino acids by the production of an amide bond. What are the
structures of these 2 amino acids?
39. A lot of controversy surrounds the use of Aspartame as an artificial sweetener. The main argument is
concerned with the production of methanol in the body. From the structure of aspartame given below:
Suggest a source for this methanol. Why is it potentially dangerous?
40. Formaldehyde is frequently used to preserve biological specimens awaiting dissection. Exposure to this
compound can be harmful. Draw its chemical structure and describe some of its biological interactions.
41. Make a summary table of organic functional groups using the heading: Name, Functional Group, IUPAC
Suffix.
42. 2-butanol is oxidized. Suggest a method a chemist could use to separate the oxidation product from the
original 2-butanol. Include the condensed formula of the oxidation product in your answer.
43. The digestion of protein in humans is done largely in the stomach by gastric juices. Why is this step of
digestion critical?
8
44. As a chemist in a research group, you are required to produce dicyclopentylether using cyclopentene as a
starting material. Propose a synthesis pathway.
45. Stick formulae can be used to sketch figures. Draw 3-ethyl-3-phenyl-4-propylheptane using a stick formula.
What would this figure be?
46. In hair salons, strong solutions of hydrogen peroxide are used to straighten curly hair or to add a permanent
wave to straight hair. In either case, how is the structure of the polymer in the hair shaft altered?
47. Although chlorofluoronitromethane has only one carbon atom, it can exist in two isomeric forms. Explain,
with the aid of a diagram, how this is possible.
48. When a person is exposed to X rays, DNA damage can result. Usually, one nucleotide is removed from the
DNA structure. In this case, no problems arise. If one or more consecutive pairs of nucleotides is removed,
complications can arise. Explain.
49. The structures of three amino acids are given below. List all the simple proteins which can be produced from
these amino acids.
50. How does boiling water destroy a bacterium's ability to reproduce?
Essay
51. Millions of tons of organic compounds are finding their way into the water systems of the world each year,
from oil spills and pollution. Describe the growing environmental problems created by this negligence and
discuss possible solutions.
52. The pulp and paper industry is a major employer in many small towns in Northern Ontario and other
provinces. Some of the by products of the pulp process include short chain carboxylic acids such as propanoic
and butanoic acid. These are produced in quantities large enough that the strong odour produced by these
acids in local streams from waste water causes concern among town residents. As an organic chemist, devise
some strategies to deal with this problem.
53. Our modern Western society relies heavily on organic compounds. Many improvements have been made in
these products to assist in solving new health, environmental and safety concerns. Describe several of these
innovations.
9
Organic-Practice
Answer Section
MULTIPLE CHOICE
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
D
E
D
A
D
C
D
B
A
B
C
A
A
D
E
C
C
D
A
B
D
B
B
C
D
B
B
C
A
D
SHORT ANSWER
31. ANS:
-
preservatives and other organic compounds may cause unforeseen health side effects (long or short term)
when ingested if they are not normally a chemical found in our bodies
high levels increase the risks of side effects
allergies, illness and even links to cancer are possible
some organic compounds react with the body's hormones or mimic the behaviour of natural hormones,
and side effects result
10
32. ANS:
- graph has slight curve as shown below
-
33.
34.
35.
36.
as the number of carbon atoms increases, Van der Waals forces increase, causing higher attraction
between molecules
- boiling points increase as a result
- boiling point of decane is 174ºC
ANS:
- condensed formula is: CH3CH2OCH2CH3
- label should include the following:
- highly flammable
- keep away from sparks and sources of heat
- high volatility
- low melting point, low boiling point
- avoid fumes, inhalation may cause unconsciousness
ANS:
- fluorinated organic compounds are not as reactive as chlorinated compounds
- the carbon-fluorine bond is stronger and more stable due to the higher electronegative fluorine
- chlorine in the body reacts with organic compounds in many unpredictable ways
ANS:
- ethanol, which is the alcohol desired for beverages had to be distilled
- it was difficult to purify since it hydrogen bonded with water and other alcohols
- ethanol was flammable leading to deaths by explosion/fire
- methanol was sometimes mixed in as a by product causing death or blindness
- high percentage concentrations of ethanol are poisonous.
ANS:
- should be hydrophobic, so water will bead up
- this will seal out moisture and its dissolved contents from attacking the paint's surface - as a result, it
should be non-polar
- must remain as a solid under high temperatures, hence long chain carbon alkanes
- must resist attack by the sun
- must be flexible when body panels flex, hence Van der Waals forces which allow molecules to slide
- must bond to the paint
11
- should not be flammable or toxic
- waxes are long chain alkanes, with few functional groups.
37. ANS:
- other answers are possible
- proper name: 1,2-ethanediol
38. ANS:
39. ANS:
- the, -CO2CH3, group on the right side could be decomposed by a strong acid (e.g., stomach acids) to
produce a hydrolysis reaction resulting in methanol
- methanol is oxidized in the body to methanal (disrupts protein) and methanoic acid (harms cells)
40. ANS:
- formaldehyde forms cross links between polypeptide (polyamide) chains changing the structure of protein
- it is also oxidized in the body to formic acid which disrupts mitochondria in cells
41. ANS:
Name
alcohol
ether
aldehyde
ketone
carboxylic acid
Functional Group
IUPAC Suffix
-ol
-ether
-al
-one
-oic acid
ester
-oate
amine
-amine
amide
-amide
42. ANS:
- add water and diethylether
- 2-butanol would dissolve in the water (polar) and 2-butane would dissolve in the diethylether
- alternate, if both are liquids, if boiling point are distinct enough distillation
43. ANS:
12
-
proteins consist of polypeptide chains which are amide linkages
the amide bonds are resistant to hydrolysis so the strong acids present in the stomach allow the proteins to
be broken apart
- smaller protein molecules are more easily absorbed by the blood
44. ANS:
45. ANS:
resembles a 'stick man'
46. ANS:
- the disulfide (-S-S-) cross links between adjacent alpha-keratin polypeptides are broken and reformed
with the desired pattern
- the secondary structure is altered without damaging the primary structure of keratin
47. ANS:
- all four groups on the carbon atom are different so it is a chiral molecule
- the two isomers are mirror images which can not be superimposed
48. ANS:
- when one nucleotide is removed, it is always replaced with the same one, since nucleotides always form
the same pairs due to H-bonding:
,
- if one or more pairs is removed, they may be replaced with the wrong pairs (i.e.,
replaces
)
- a new amino acid may be coded for in a protein leading to cancer or other complications (e.g., inactive
proteins, performs another function)
49. ANS:
- gyl-ala
- gly-ala-ser
- gly-ser
- gyl-ser-ala
- ala-ser
- ala-gly-ser
50. ANS:
- high temperatures cause the DNA to 'melt' (unzip), making replication difficult
- proteins denature interfering with cell processes
ESSAY
51. ANS:
answers may vary
13
-
oil spills are especially dangerous since the oil floats on top of the water (density of oil is less than
water), and spreads over great distances
- it takes a long time to break down the oil naturally
- deprived of light, algae and aquatic plants die
- fish and other water animals are coated with oil which can not be washed off
- this reduce their ability to breathe, swim, fly or maintain a proper body temperature
- lighter oil compounds may be ingested and prove to be toxic
- insoluble in water, oil washes onto beaches and destroys life on land
- other pollution sources from landfills, household, agricultural and manufacturing compound problems by
dumping toxic compounds which react with each other in unpredictable way
- many are harmful to biological systems (alkyl organics)
- many pesticides and other 'unnatural' organics stay active in the environment for decades
- biomagnification represents a danger to human
- education, strict legislation/enforcement and reduction in the use of dangerous organic compounds will
assist the problem
52. ANS:
- do not dump the 'waste' water directly into the streams but place in holding lagoons
- in this way, the water can be treated before being released into streams
- carboxylic acids can be reduced into biodegradable alcohols
- carboxylic acids can be reacted with alcohols selected to make esters which do not have foul odours and
are inviting to bacteria which will consume them
- react the carboxylic acids with a base to make an insoluble salt which can be removed from the bottom of
the lagoon, and the clear water on top can be released into the stream
53. ANS:
answers will vary
- farmers use the potency of pheromones to attract and kill insects as an alternative to pesticides
- HFCs are replacing CFCs as propellants, since they do not contain chlorine and will damage the ozone
layer
- synthesis of polymers for high density optical storage
- use of unleaded gasoline in place of leaded gasoline
- alterations in transparent polymers to prevent damage form lasers in pilots eyes, improve optical networks
- use of recyclable organic products in packaging and automotive products
- preservatives in foods to prevent spoilage
- biodegradable pesticides in place of long lasting alkyl organics such as DDT
- improved analytical testing for organic compounds in our bodies (e.g., hormone levels, proteins)
- newly synthesized antibiotics to fight disease
- alternative medicines: use of aldehydes in aromatherapy
- production of new artificial sweeteners such as saccharin to help diabetics, people on diets in place
dangerous products such as aspartame