Knowledge
Name: _____________________
SCH 4U – Organic Chemistry Problem Set
Communication
Inquiry
Application
/18
Section A: Multiple Choice – (
/28
/26
/24
/ 18 ) marks
Identify the letter of the choice that best completes the statement or answers the question.
____
1. What results when a secondary alcohol is oxidized?
a. a ketone
d. an acid
b. an amine
e. no reaction
c. an aldehyde
____
2. The general formula for a cycloalkane can be represented by which of the following?
a. CnHn
c. CnH2n
b. CnH2n+2
d. CnH2n-2
____
3. Which type of reaction will an alkene not undergo?
a. addition
d. dehydration
b. polymerization
e. hydration
c. oxidation
____
4. Which group of these compounds tends to be the most reactive?
a. alkanes
c. alkynes
b. alkenes
d. aromatics
____
5. Butane and fluorine gas would react by which of the following?
a. addition
c. substitution
b. combustion
d. single displacement
____
6. The alcohol below is classified as which of the following?
a. primary alcohol
b. secondary alcohol
____
c. tertiary alcohol
d. aromatic alcohol
7. How many double bonds would be in one of the resonance structure of aromatic napthalene?
a. 5
b. 6
c. 0
d. 12
1
____
8. The synthesis sequence shown here is best described as which of the following?
1.
____
2.
3.
a. (1) Dehydration; (2) halogenation; (3) hydrogenation
b. (1) Hydrogenation; (2) dehydration; (3) halogenation
c. (1) Hydrogenation; (2) halogenation; (3) dehydration
d. (1) Halogenation; (2) hydrogenation; (3) dehydration
e. (1) Dehydration; (2) hydrogenation; (3) halogenation
9. Which of the following compounds is 4-iodo-6-cyclopropyl-3-hexanone?
a.
c.
b.
d.
____ 10. Which compound is most likely to be a gas at room temperature?
a. propane
c. propanal
b. 2-chloropropane
d. propanone
____ 11. From the following list, select the two molecules that are isomers:
1. CH3CH2CH2CH2CH3
2. CH3CH2CH2CH(CH3)2
3. CH3CH2CH2CH3
4. CH3CH2CH(CH3)CH2CH3
a. (1) and (2) only
b. (1) and (3) only
c. (1) and (4) only
d. (2) and (3) only
e. (2) and (4) only
2
____12. In order to prepare the molecule shown below, which organic compounds must a chemist react under the
appropriate catalyst/conditions?
a.
b.
c.
d.
____ 13. The compound shown below can be prepared by which of the following?
a.
b.
c.
d.
substitution of benzene with chlorobenzene
condensation of hydroxybenzene (phenol)
hydrogenation of diphenylmethanone
oxidation of diphenylmethane
____ 14. A cosmetic company wants to produce nail polish remover, also known as acetone,
,
from propene. An efficient method would involve the following series of reactions in which order?
a. halogenation, oxidation
c. reduction, halogenation, elimination
b. reduction, hydration
d. hydration, oxidation
3
____ 16. The polymer formed from lactic acid (structure shown below) is used for surgical sutures. The polymer
structure is best represented by which of the following?
(lactic acid)
a.
c.
b.
d.
____ 17. What is the monomer for the polymer Kel-F shown below?
a.
c.
b.
d.
____ 18. 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
Communication (24 Marks)
Explain why it is important to know Markovnikov’s rule when trying to predict the products of addition reactions to
alkenes and alkynes. Illustrate your explanation with an example. (4 marks)
4
Name the following structures using IUPAC conventions – ( Communication
a)
H3C
CH2
C
C
CH3
b)
H3C
CH2
CH2
CH2
/6 marks)
CH
CH3
CH2
CH3
c)
OH O H
H C
H
C H
H3C
CH2 CH2 O
CH2 CH2 CH3
H
e)
H3C
d)
f)
O
CH2 CH2 CH2 CH2 C
CH2 CH2 CH3
NH2
H3C
CH2 CH CH3
Draw the following structures using structures that show all atoms – (Communication
marks)
a) bromocyclopropane
b) octanal
c) decanamide
d) ethyl methanoate
/6
5
e) hexanoic acid
f) m-dimethylbenzene
Section D: Name the following more complex structures – (Communication
a)
/ 6 marks)
b)
O
CH2 CH2 C
H3C
O
CH3
CH3
CH2 CH2 C O
C CH3
CH3
CH2 C OH
CH3
O
c)
H3C
CH2 NH CH2 CH2 CH3
d) H C
3
CH2 CH2 CH2 C
N
CH3
CH2
CH2
CH3
e)
O
H C
F
CH2
H3C
f)
CH2 C F
F
H3C
CH2
OH
6
Section E: Draw the following more complex structures – (Communication
a) phenylmethanoic acid
b) 1,5 – diaminopentane
c) 3-sec-butylhepta-1,3-diene
d) diphenylmethane
e) methoxypropane
f) N,N-dipropyl propanamide
Section F: Fill in the blanks to complete the following reactions (Inquiry
/ 6 marks)
/ 26 marks)
combustion
a)
C3H8 (g) + 5O2 (g)
+
Type of reaction: _________________
H
b)
H C
H
H
C H + Cl Cl
H
UV
+
Type of reaction: _______________
7
Room
c)
+
Br
Temp.
Br
Br
Br
H C
C
H
H
Type of reaction: _______________
d)
H
CH3
AlCl3
+
CH2
+ H Cl
Type of reaction: ______________
e)
H2C
H
H
C
C H +
H
H
OH
O
H3C
H
CH CH3
Type of reaction: _________________
H2SO4
H3C
f)
CH2
+
H3C
OH
CH2
O
CH3 +
Type of reaction: ________________
g)
OH
H3C
+
CH2
(O)
+
oxidizing agent
Type of reaction: _______________
h)
O
Pt catalyst
+
H2
heat, pressure
Type of reaction: _______________
8
Kevlar, a strong polymer used in bullet proof vests, is made by the following condensation of monomers(2 marks)
and
The structure of the polymer Kevlar is:
/2
___________________________________.
The structure of the monomer that must be used to produce the polymer given below is:
/2
____________________________________.
When a straight chain alcohol is reacted with H2SO4,
, and
are both formed.
The structure of the original alcohol was:
/2
___________________________________.
Application: Answer the following short answer problems - 4 marks each. (Application /24 marks)
1. Describe the difference between a 1, 2, and 3 amine. Does ammonia (NH3) fit in one of these amine
classifications, why or why not?
/4
9
2. Given ethyl iodide (CH3CH2I) and ammonia (NH3), show how with successive reactions you would be
able to eventually synthesize triethylamine. In each successive step show your reactants and products.
H3C
CH2 N
CH2 CH3
CH2
CH3
triethylamine
/4
3. An inattentive grade 12 chemist, decides to try to make some moonshine to drink on Friday evening.
Unfortunately, all that is available is an ester compound - methyl ethanoate and a strong base NaOH. The
chemist decides to combine these chemicals to undergo a hydrolysis reaction in order to produce his beverage
of choice.
I) Show the complete hydrolysis reaction.
II) Assuming that this chap devises a perfect means to separate his reaction products, why should
this chemist still refrain from consuming his drink and what are the implications of sipping from this
alcoholic beverage?
/4
10
4. Explain why must aldehydes and ketones can only be synthesized from specific types of alcohols (ie. 1 or
2). Give an example of this synthesis. Why cannot a 3 alcohol be used to create an aldehyde or ketone?
/4
5. Draw the structural formula for each of the four isomers of butyl chloride (C4H9Cl). Name each isomer.
/4
6. Use structural formulas to write the equation for the reaction of acetic acid (CH3COOH) with each of the following
compounds. (4 marks)
a) ethylamine
/2
b) butan-1-ol
/2
11