SCH4U Ms.

Wilson
Name: ________________________________________ 9th March 04
Test Unit #1
Organic Chemistry
Multiple Choice
Identify the letter of the choice that best completes the statement or answers the question and write it on the
multiple choice answer sheet provided..

1.When two alcohols undergo a self condensation, what is formed?

a. liquid alcohol d. an aldehyde
b. a ketone e. an ether
c. an ester

2.How many actual double bonds does the benzene ring possess?
a. 4 d. 1
b. 3 e. 0
c. 2

3.

The correct name for the compound given above is which of the following?
a. 2-methyl-1-butene d. 3-methyl-2-butene
b. pentene e. 2-ethyl-1-pentene
c. 2-ethyl-1-propene

4.

The compound above is classified as a(n)

a. alkane d. ketone
b. carboxylic acid e. alkene
c. aldehyde

5.Which of the following is a secondary alcohol?

a. d. CH3OH

b. e. CH3CH2OH
 c.

6.What results when a secondary alcohol is oxidized?

a. a ketone d. an acid
b. an amine e. no reaction
c. an aldehyde

7.Which statement is incorrect concerning these two molecules with the same formula, C2H6O?

I. II.

a. compound (II) will more likely be soluble in water than compound (I)
b. compound (I) will have a lower boiling point than compound (II)
c. hydrogen bonding will be the most likely for compound (II)
d. the vapour pressure of compound (II) will be lower than that of compound (I) at a given
temperature
e. compound (I) would be a better solvent

8.The general formula for a cycloalkane can be represented by which of the following?
a. CnHn c. CnH2n
b. CnH2n+2 d. CnH2n-2

9.

The correct name for the compound given above is which of the following?
a. 3-amino-3-hexanone c. N-propylpropanamide
b. ethyl ethanamide d. N-ethylethanamide
10. The product formed by the reaction of CH3CO2H with

is properly named
a. N-ethyl-N-methylethanamide c. N,N-diethylmethanamide
b. N,N-diethylaminomethane d. N-ethyl-N-methylmethamide

11.The correct structure for 1-methyl-2,4,6-trinitrobenzene(TNT) is which of the following?

a. c.

b. d.

12.The condensed formula of 2,3,4-trimethylpentane is which of the following?

a. c.

b. d.
13.

The correct IUPAC name for above compound is which of the following?
a. fluorobutanoic acid c. 2-fluoro-2-nitrobutanoic acid
b. 3-fluoro-3-nitrobutanoic acid d. 3-fluoro-2-nitropropanoic acid

14.1-amino-4,4-difluoro-2-pentanol is the correct name for which of the following compounds?

a. c.

b. d.

15.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

16.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

17.Which of the following classes of organic compounds does not contain oxygen?
a. aldehydes d. ethers
b. amines e. amides
c. amino acids
18. The correct structure for 1,4-dicyclopropylcyclohexane is which of the following?
a.
a. c.

b. d.

19. Which of the following compounds can produce an addition polymer?

a. c.

d.
b.

20.Which one of the following contains compounds from which a condensation polymer can be produced?

a. and

b.

and

c.

and

d.
and
True/False [10]
Indicate whether the sentence or statement is true or false. If false, change the identified word or phrase to
make the sentence or statement true.

____ 1. The reaction of an ester with a strong acid is known as saponification.

_________________________
____ 2. Carbon-carbon double and triple bonds are more reactive than carbon-carbon single bonds.
_________________________
____ 3. CH4 has a higher melting point than CH3OH. _________________________
____ 4. Alkanes react with halogens in an addition reaction at room temperature.
_________________________
____ 5. When benzene reacts with bromine gas, the bromine atom replaces one of the hydrogens on the
benzene. _________________________

Short Answer
[25]
Answer to the following questions on the paper provided.

1. A chemist is required to make the compound below for her company. Propose a one step synthesis that will
save the company time and money.

2. 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.

3. When a worker-bee stings, it emits a substance with the molecular formula C7H14O2. This acts as a signal,
attracting other bees to the site and prompts them to sting too. When this sweet smelling compound is treated
with a strong acid (H2SO4), acetic acid and 2-methyl-1-butanol are formed. Draw the structure and provide the
IUPAC name of the emitted compound.

4. Moth balls prevent many insects and small rodents from eating/nesting in certain locations.
Paradichlorobenzene is present in high quantities in moth balls. Draw the chemical structure for this
compound and suggest reasons why it is an effective repellent.

5. In the future, you are employed as an organic chemist in a petrochemical company. The work day is almost
finished when you realize that you forgot your perfume/cologne for your date that evening. You decide to
quickly prepare the ester,

, from 3-phenyl-1-propene and ethene.

Describe the process you would use.
Essay
[25]
Answer to the following questions on the paper provided.
1. Since their introduction, plastics have revolutionized modern manufacturing. With modifications
in their chemical structure, they can be utilized in thousands of products. Discuss the variety of
plastic usages in our society and the complications associated with their eventual disposal. [10]
2. Polymers are often thought to be manufactured in immense chemical plants. Although many are,
there is a large group of polymers which are natural. Describe several natural polymers and how
they are utilized in our society. [5]
3. Make a summary table of organic functional groups using the heading: Name, Functional Group,
IUPAC Suffix. [10]

Bonus [4]
1. 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? [2]

2. In the design of a new baby diaper, the manufacturer uses two polymers. The structure of these
molecules is given below. Which polymer is best suited to the outside of the diaper and which to
the inside? [2]

,
(I) (II)
Name: ____________________________________________ Organic TEST-9/03/04

1. ___ 6. ___ 11. ___ 16. ___

2. ___ 7. ___ 12. ___ 17. ___
3. ___ 8. ___ 13. ___ 18. ___
4. ___ 9. ___ 14. ___ 19. ___
5. ___ 10. ___ 15. ___ 20. ___
Organic chemistry test
Answer Section

MODIFIED TRUE/FALSE

1. ANS: F, use a strong base REF: K/U OBJ: 1.7

LOC: OC1.03
2. ANS: T REF: K/U OBJ: 1.1
LOC: OC2.01
3. ANS: F, lower REF: K/U OBJ: 1.1
LOC: OC1.02
4. ANS: F, Alkenes REF: K/U OBJ: 1.3
LOC: OC1.03
5. ANS: T REF: K/U OBJ: 1.4
LOC: OC1.03

SHORT ANSWERS
1. esterification reaction

- water is removed by taking -OH from the acid, H from the alcohol
- C in carbonyl, bonds to O in the alcohol, forming a ring

2. 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

3. - is an ester

- 2-methylbutylethanoate

5.
ESSAY

1. ANS:
answers may vary
- plastic usage includes:
- packaging, insulation on wires, storage containers (e.g., food), construction materials,
household items such as furniture, disposable cutlery, diapers, car components, safety
packaging on food and drugs, contact lenses, etc.
- various plastics differ in substitutions on monomers of ethene
- different substituted groups allow hydrogen bonding, cross-linking (-S-S-bonds, and dienes),
and various strengths of Van der Waals forces
- characteristics such as strength, rigidity, waterproofing can be altered as a result
- common plastics include polyethylene, polypropylene, polystyrene and polyvinylchloride
- these are identified by a number inside the recycling triangle on containers
- 30% of all landfill content is plastics
- poor biodegradability is a problem
- incineration of plastics creates less ash and creates less CO2 than the equivalent mass of
paper
- incineration of some plastics such as polyvinylchloride creates HCl
- other plastics are not easily recycled creating an enormous waste problem (e.g,. plastic in
older computers)

REF: C OBJ: 2.1 LOC: OC2.01

2. 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
- 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

REF: MC OBJ: 2.2 LOC: OC3.01

3.
Name Functional Group IUPAC Suffix
alcohol -ol
ether -ether
aldehyde -al

ketone -one

carboxylic acid -oic acid

ester -oate

amine -amine

amide -amide

BONUS
1.

2. (II) is hydrophobic (non-polar), so it would prevent leakage of water to the outside

- (I) will allow water to mix with the lining to absorb water
- (I) should be on the inside
- (II) should be on the outside