Download Part B: Short Written Response - bourre-chem-11

Name: ________________________________
Date: ___________________________
SNC 4C
Organic Chemistry Test
Part
Total marks
A. Multiple Choice
36
B. Short Answer
85
Student mark
121
Part A: Multiple Choice
Please place the letter corresponding to the best answer in the space to the left of each question.
Use the following choices to identify the family of compounds to which the compounds in question 1 to
18 belong. (Each one is used at least once, but may be used more often.)
a) alkyl or aryl halides
b) alcohols
c) aldehydes
d) ketones
e) carboxylic acids
f) esters
h) hydrocarbons
i) ethers
______ 1. C3H7OH
______ 2. Ethanoic acid
______ 3. Acetone
______ 4. CH3CH2CHO
______ 5. CH3CBr2CH2CH2CH3
______ 6. CH3 CH2CH2CHO
______7. Cyclopentane
______8. Methyl salicylate
______9. 2-Propanol
______10. CH3CH2CH2CH2COOH ______11. CH3COOCH2CH2CH3
______12.CH3OCH2CH2CH3
______13. Methoxymethane (also called dimethyl ether... but not used for naming in this course)
______15. The result of the addition reaction between an alkene and water (HOH).
______16. A compound used as a natural flavouring. (Most of these smell sweet.)
______17. Some of these are causing a deterioration of the ozone in our atmosphere.
Organic Chemistry Test
______14. The result of the condesation reaction between a carboxylic acid with an alcohol.
(You did this in a lab.)
1
______18. Choose the correct statement:
a) Aromatics like benzene have no real double bonds and therefore undergo addition
reaction sand seldom take part in substitution reactions.
b) Aromatics like benzene have no real double bonds and therefore undergo substitution
reactions and rarely undergo addition reactions.
c) Aromatics undergo both addition and substitution reaction easily.
______19. The smallest cycloalkane is:
a) cycloethane
c) cyclopropane
b) propyl-2-butene
d) benzene
______20. Fermentation of glucose gives:
a) methanol
b) ethanol
c) ethanediol
d) propanol
______21. Which alcohol can be consumed by the human body in moderation, without causing adverse
side effects?
a) methanol
b) ethanol
c) ethanediol
d) propanol
______22. Aldehydes and ketones both contain the carbonyl group(an O double bonded to a carbon).
How are they different?
a) aldehydes have the carbonyls attached at the end of the carbon chain
while ketones have the carbonyl attached in the middle somewhere
b) ketones have the carbonyls attached at the end of the carbon chain
while aldehydes have the carbonyl attached in the middle somewhere
c) aldehydes have the carbonyls attached at the both ends of the carbon chain
while ketones have only one carbonyl attached
c) butanal
_______24. Which of the following cannot be an isomer of C5H12O?
a) an alcohol
b) a ketone
c) an ether
d) 2-pentanol
_______25. The formula for propyl ethanoate is
a) CH3CH2 CH2COCH2CH3
c) CH3OCH2CH3
b) CH3COOCH3
_______26. When pentanoic acid reacts with ethanol the product is
a) ethyl pentanoate
b) ethyl propionate
c) pentyl ethanoate
Organic Chemistry Test
_______23. The shortest ketone is:
a) methanone
b) propanone
d) methanal
e) 1-ketone
2
_______27. During esterification, condensation occurs as water is produced. Please choose the most
correct statement:
a) An –OH group is lost from the carboxylic acid, while the –H is lost from the alcohol.
b) An –OH group is lost from the alcohol, while –H is lost from the carboxylic acid.
c) Both a) and b) are true.
d) Both a) and b) are false.
_______28. Which statements are true about addition and substitution reactions?
a) A substitution reaction fills = and ≡ bonds with atoms.
b) An addition reaction kicks out another atom.
c) Both a) and b) are true.
d) Both a) and b) are false.
_______29. What is not true about ethers:
a) The longest chain is written first in the name.
c) The name is written as one word.
d) They are insoluble in water.
e) They have boiling points similar to alkanes, alkenes, and alkynes.
_______30. The incomplete combustion of a hydrocarbon can result in the formation of
a) carbon (soot), carbon monoxide, other by-products
b) carbon and hydrogen
c) carbon dioxide and water vapour
_______31. When a candle burns, the mass of the candle decreases. Why is this so?
a) because the candle melts
b) because the candle evaporates
c) because the wax is turned into carbon dioxide and water vapour
_______33. Which reaction would form occur if propane was burned?
a) addition
b) substitution
c) combustion
d) reforming
e) cracking
_______34. Which reaction would form ethanol from an unsaturated hydrocarbon?
a) addition
b) substitution
c) combustion
d) fermentation
e) cracking
Organic Chemistry Test
_______32. Which of the following is a balanced equation for the complete combustion of methane?
a) CH4 + O2  CO2 + H2O
b) CH4 + 2O2  CO2 + H2O
c) C2H6 + 3O2  2CO2 + 3H2O
3
_______35. The process of separating petroleum into its fractions is called:
a) refining
b) boiling
c) condensation
d) fermentation
e) distillation
_______36. Which statements are true about the oil refining process?
a) Fractions that have higher boiling points settle at the bottom, and fractions with lower
boiling points settle to the bottom.
b) Fractions that have lower boiling points settle at the bottom, and fractions with higher
boiling points settle to the bottom.
c) The boiling point depends on the length of the carbon chain.
d) Both a) and c) are true.
e) Both b) and c) are true.
Part B: Short Written Response
1. In a complete sentence, please describe what the structural difference is between an ether and an ester.
(1 mark)
3. Please explain why are alkenes more reactive than alkanes, in spite of the fact that double bonds are
“stronger” than single bonds? (1 mark)
Organic Chemistry Test
2. In a complete sentence, please describe what the structural difference is between an alkane and an
alkene. (1 mark)
4
4. Why does a carboxylic acid have a higher boiling point than an alkane? (1 mark)
5. Why are 1-propanol and 2-propanol considered to be isometric? What do they have in common?
(1 mark)
6. Ethers and alcohols are isomers. Draw two isomers of C2H6O. Make one an ether and the other an
alcohol and label them as such. (3 marks) (You may name them for bonus marks.)
CH3COOH
+
HOCH2CH2CH3

HOH +
Organic Chemistry Test
7. You performed an experiment in which you made esters. Complete the following esterification
reaction. Sulfuric acid, H2SO4, is used as the catalyst.) (2 marks)
5
8. a) Put the following molecules in order of increasing boiling point. (2 marks)
HCOOH
CH4
CH3OH
CH3F
b) The bonding of atoms other than hydrogen to carbons has the effect of making the molecules polar.
One effect of this polarity is to increase melting and boiling points. What is one other effect? (1 mark)
c) Molecules with an H bonded to an O (like alcohols and carboxylic acids) have even higher melting
and boiling points because of their “hydrogen bonding” to adjacent molecules.
Which of the following would probably have the higher boiling point? Please explain. (2 marks)
CH3CH2CH2OH
Organic Chemistry Test
HOCH2CH2OH or
6
9. Complete the following substitution and addition reactions using structural formulas. Identify the
reactions as substitution or addition. (3 marks each... 18 marks)
a) propane and chlorine (with UV light)
b) propene reacts with chlorine
c) propene reacts with HBr
d) HC≡CH and bromine
f) 1-butyne with excess hydrogen bromide (show this as one step)
Organic Chemistry Test
e) cyclopropane with fluorine
7
10. Please complete and balance the following combustion reactions. There is excess oxygen, so these
will be complete combustion reactions. (3 marks each... 9 marks)
a) Ethane (C2H6) + oxygen 
b) Ethene (C2H2) + oxygen 
c) Ethyne (C2H2) + oxygen 
11. Please name the following: (1 mark each... 15 marks)
a) C2H5OH
_________________________
b) CH3CH2CH2CHO
_________________________
c) CH2=CHCH2CH3
_________________________
d) CH3CH=CHCH=CH2
_________________________
e) HC≡CH
_________________________
f) HC≡ CCH2
_________________________
g) CH2Br
_________________________
h) CH3CH2Br
_________________________
i) CH3CH2CH2Br
_________________________
j) CH3CH2CHBrCH3
_________________________
k) CH3CH2CH2CH2Br
_________________________
l) CH3CH2CH2CH2CH2COOH _________________________
m) CH3COOCH2CH2CH2CH3
_________________________
n) CH3CH2OCH2CH2CH3
_________________________
o) CH3(CH2)8COOH
_________________________
Organic Chemistry Test
(Hint: use “di” for naming the double bonds)
8
a) propane
j) propanal
b) 1,2-dibromopentane
k) Octanal
c) cyclopentane
l) propanone
d) methylpropane
m) 2-octanone
e) 1-butene
n) propanol
f) 2-pentyne
o) 2-butanol
g) methoxyethane
p) methanoic acid
h) ethoxypropane
q) ethanoic acid
i) Methyl ethanoate
r) methyl propanoate
Organic Chemistry Test
12. Draw structural diagrams for the following: (1 mark each... 18 marks)
9
28. The boiling point of an alcohol is always higher than the boiling point of an alkane with the same
number of carbons. Use the data in the table below to state the pattern between the molecular formula and
the boiling point of alcohols. (2 marks)
Systematic Name
Condensed Formula
Boiling Point.(°C)
Methanol
CH3OH
65
Ethanol
C2H5OH
78
1-Propanol
C3H7OH
97
1-Butanol
C4H9OH
118
1-Pentanol
C5H11OH
138
_____________________________________________________________________________________
_____________________________________________________________________________________
_____________________________________________________________________________________
29. The carboxylic acid functional group, -COOH, is present in a variety of common chemical substances.
This Table provides some information on six such compounds; their structural formulae are shown below.
Please complete the table by writing in the matching letter of the structural formulae to the names in the
table. (8 marks)
Systematic name
Common name
Natural Occurrence
Methanoic acid
Formic acid
Wood ants (Formica rufa)
2-Hydroxypropanoic acid
Lactic acid
Sour milk, Active muscles
Citric acid
Citrus fruits; e.g., sweet
oranges (Citrus sinensis)
Acetic acid
Vinegar
2-Hydroxypropane-1,2,3-tricarboxylic acid
Ethanoic acid
A)
B)
C)
D)
Organic Chemistry Test
Letter
1
0