Full Name: ________________
Date: ________________
SCH4U Organic Chemistry Unit Test –Oct. ‘09
Multiple Choice (K/U)
____
____
Identify the letter of the choice that best completes the statement or answers the question.
1. An amine is characterized by what functional group?
a. -CO2CH3
d. -CHO
b. -NH2
e. -OH
c. -CO2H
2.
The compound above is classified as a(n)
a. alkane
b. carboxylic acid
c. aldehyde
____
d. ketone
e. alkene
3.
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
____
4.
____
The correct name for the compound given above is which of the following?
a. 1,3-cyclopentadiene
c. 1,4-cyclopentene
b. 1,4-cyclopentadiene
d. 1,3-cyclopentene
5. The reaction of CH3CH=CH-CH=CH2 with excess bromine gives chiefly
a. 1,2-dibromo-3-pentene
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
6.
____
The correct IUPAC name for the compound above is which of the following?
a. 5-ol-2-ethylpentane ether
c. 3-propoxypentanal
b. 2-ethoxy-5-pentanone
d. 4-ethoxypentanal
7. Which of the following is the correct name for the structure below?
____
____
a. trans-4-nonyne
c. trans-4-nonene
b. cis-5-nonene
d. cis-4-nonene
8. In a chemistry lab test, you are asked to react a solution of bromine with each of the following unknown
liquids. Which one decolourizes the bromine solution?
a. 2,3-dimethylbutane
c. cyclohexene
b. ethanoic acid
d. n-methylmethanamide
2
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9. The correct synthesis of n-octane would involve which of the following reactions?
a. dehydrogenation of 2-octene
c. hydrogenation of 3-octene
b. halogenation of 4-octene
d. reduction of isooctane
____ 10. When CH4 is reacted with excess Cl2(g) in the presence of light, the reaction mixture contains which of the
following?
a. CH3Cl
c. CH3Cl, CH2Cl2, CHCl3
b. CH2Cl2
d. CHCl3
____ 11. 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
____ 12. The correct name for the compound given below is which of the following?
____ 13.
____ 14.
____ 15.
____ 16.
____ 17.
a. 1-phenyl-1-butanone
c. 4-phenyl-4-butanone
b. phenylbutanal
d. butanonebenzene
The melting point of a compound is not influenced by which of the following?
a. polarity
d. hydrogen bonds
b. electronegativity of its atoms
e. isotope of carbon
c. Van der Waals forces
Which of the following compounds is a secondary alcohol?
a. 1-pentanol
c. 2-pentanone
b. 2-pentanol
d. 2-methyl-2-butanol
Ethanoic acid (vinegar) when diluted to low concentrations by water can be prepared from ethene by
a. reduction with H2, followed by reaction with a strong oxidizer
b. addition of HCl, followed by reaction with H2O
c. addition of H2O followed by reaction with a strong oxidizer
d. addition of Br2, followed by reduction with H2
The primary structure of a protein involves which of the following?
a. Van der Waals forces
d. peptide bonds
b. hydrogen bonds
e. disulfide bonds
c. hydrophilic forces
Which of the following carbohydrates are isomers?
a. galactose and glycogen
d. cellulose and starch
b. galactose and fructose
e. glycogen and lactose
c. fructose and glucose
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____ 18. Which of the amino acids given below is the most likely to form cross linking in the secondary structure of a
protein?
a.
c.
b.
d.
____ 19. Which one of the molecules below has a chiral (optical) isomer?
a.
c.
b.
d.
____ 20. Which of the following compounds can produce an addition polymer?
a.
c.
b.
d.
Short Answer (I/C) – 2 marks each
21. 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.
22. In household fires, it is often the smoke produced that creates a danger as great as the flames. Many plastic
materials in the house contain polyvinylchloride (PVC); the formula for this compound is (C2H3Cl)n. Write an
equation for the combustion of PVC in oxygen. Suggest a reason why its incineration poses a serious risk
during a fire.
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23. Propane can be used as starting material for either propanal or propanone. Explain how this is possible.
24. 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.
25. The structure given below is PenicillinG, an antibiotic. Circle the functional groups in the molecule and list
their corresponding names.
26. During a school laboratory test, you are given 2-pentyne and asked to prepare 2-pentanone and 3-pentanone
from it. Develop a synthesis pathway to accomplish this task.
27. The structure given below is a polymer classified as a polyamide. This polymer is stable in temperatures
above 350°C, and can be used as a protective coating on hot surfaces. What monomers were used to make this
polyamide?
28. Formaldehyde (methanal: H2C=O) can be polymerized to produce Delrin (polyoxymethylene), a strong and
easily molded plastic. Write a chemical reaction that shows the formation of this polymer.
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29. Nomex is a polymer used to make flame-resistant clothing for firefighters. A portion of its structure is
provided below. Write a polymerization reaction showing its production from monomers. What type of
reaction is this?
30. The structures of three amino acids are given below. Draw and label 4 simple 2 amino acid polypeptide
structures which can be produced from these amino acids (example of structure label: gly-ala).
Essay (MC) Answer only ONE of the following questions. (8 marks)
Provide sufficient detail and supporting points. Answer in an organized paragraph.
31. Designing a new pharmaceutical drug to treat an illness or chronic condition is an enormous challenge.
Describe some of the problems encountered in the manufacture and utilization of a new medicine. Discuss
thalidomide and explain the issue of chirality (stereoisomers or enantiomers).
32. Polymers are often thought to be manufactured in immense chemical plants. Although many are, there is a
large group of polymers which are natural (biopolymers). Describe several natural polymers and how they are
utilized in our society or in our bodies.
M.C.
Short Ans.
Essay
K/U
I, C
MC
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20
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20
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*** marked by: (first & last name):
__________________________
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Organic-Oct09 Answer Section
1B
8C
15 C
SHORT ANSWER
21. ANS:
2C
9C
16 D
MULTIPLE CHOICE
3D
4A
10 C
11 A
17 C
18 B
5D
12 A
19 C
6D
13 E
20 A
7D
14 B
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derivatives & breakdown products in the body could include benzene and other aromatics known to be
carcinogens.
- 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
22. ANS:
- (C2H3Cl)n + 5/2 n O2  2nCO2 + nH2O + nHCl
- HCl produced, is a strong acid
- choking is caused by its corrosive influence
- other nitrogen containing products can also provide cyanide compounds (-CN:) during a fire.
23. ANS:
[O]
CH3CH2CH2OH
Cl2
water
O
CH3CH2CH2Cl
O
OH
hv
NaOH
water
[O]
'Tis true -- the hardest question on the test -- Mr. S
24. 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
25. ANS:
- aromatic ring
- two amide groups
- carboxylic acid group
- (thioether group, -S-)
26. ANS:
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27. ANS:
- is a polyamide polymer
- monomers are:
,
28. ANS:
29. ANS:
condensation reaction
30. ANS: (and ideally the –COOH and –NH2 ends should be indicated) P.S. which combo is missing?
Each of the ones below could also be re-written in the opposite order
- gyl-ala
- gly-ala-ser
- gly-ser
- gyl-ser-ala
- ala-ser
- ala-gly-ser
ESSAY
a… ..
31. ANS: answers will vary
- during a synthesis, minor products are often created in addition to major ones
- this will require constant purification since minor products could be very harmful
- isomers are often some of the minor products and are difficult to separate since they have physical and chemical
properties similar to desired products
- chiral isomers can be produced and be detrimental in biological systems where chirality is often important to
enzymes
- administering the drug: the digestion system or the pH of the blood may destroy it – IT IS A CHALLENGE TO
GET IT INTO THE CELL or INTO THE NUCLEUS IF NEEDED.
- unforeseen reactions with hormones, enzymes or other cellular proteins can cause side effects from other products
32. ANS: answers may vary
- cellulose: occurs in plants as a polymer of glucose
- since it is insoluble in water and strong, it is used as a building material (i.e., wood), often pressure-treated to
increase its life span; paper products are also made from cellulose
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-
silk is spun by the silk worm: it is dyed and used as a fabric
cotton is produced by the cotton plant: it is dyed and used as a fabric
rubber is from the sap of a rubber tree: it is vulcanized to increase stiffness by cross-linking
DNA in our cells: genetic scientists study the blue prints of life; biotechnologists manipulate DNA in other
organisms to create medicines, hormones, etc.
protein in living organisms: replacement proteins are synthesized to cure diseases, help nutrition
keratin in nails and hair: cosmetic changes in hair with perms, etc.
amber is a natural rein: fossil records, jewelry
wool from sheep: dyed and made into fabrics
glycogen is a glucose polymer in humans, for storage of energy
starch is a glucose polymer found in many plants: provides a source of energy for the human body