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SCH 4UO
Name:
PRACTICE ORGANIC CHEMISTRY TEST - ANSWERS
Part A: Nomenclature (18 marks)
1.
60
Name the following organic compounds: (8 marks)
a.
CH
O
3
CH3 CH CH2 C CH3
4-methylpentan-2-one
b. CH3 CH2 O CH2 CH CH2 CH3
CH3
ethoxy-2-methylbutane
F
c.
F
d.
meta-difluorobenzene or 1,3-difluorobenzene
CH3 N CH2 CH2 CH3
H
N-methylpropanamine
2.
Draw condensed structural diagrams for the following compounds: (10 marks)
a. 3-methylhexanoic acid
CH3
d. 3-methylbutan-2-one
O
CH3 CH2 CH2 CH CH2 C
O CH3
CH3 C CH CH3
OH
b. N-propyl-2-methylpentanamide
O CH3
CH3 CH2 CH2 NH C CH CH2 CH2 CH3
e. trans-2,3-dibromopent-2-ene
Br
CH3 C C CH2 CH3
Br
c. 2-methylbutanal
CH3
O
CH3 CH2 CH C
H
4
Part B: Reactions (14 marks)
3.
For the following reactions, draw the reactants, draw the products and name them.
a. The condensation reaction of 2-methylpropanol and butanoic acid in the
presence of sulfuric acid and heat. (3 marks)
O
CH3
CH3 CH CH2 OH
+
CH3
C CH2 CH2 CH3
O
 CH3 CH CH2 O C CH2 CH2 CH3
H 2 SO4

HO
2-methylpropyl butanoate
+ H2O
b. The oxidation of 3-methylheptanal. (2 marks)
CH3
CH3
O
+ [O] → CH3 CH2 CH2 CH2 CH CH2 C
CH3 CH2 CH2 CH2 CH CH2 C
O
OH
H
3-methylheptanoic acid
c. The addition of water to 2-methylbutene (give the minor and the major product).
(3 marks)
CH3
CH3 CH2 C CH2
CH3
+ HOH →
CH3 CH2 C CH3
CH3 CH2 CH CH2
or
OH
2-methylbutan-2-ol
major product
4.
CH3
OH
2-methylbutanol
minor product
For the following reactions, draw the products, draw the reactants, and name the
reactants.
a. _______ + _______  propyl ethanoate + water (3 marks)
O
O
CH3 CH2 CH2 OH
propanol
+
HO C CH3
ethanoic acid
→
CH3 CH2 CH2 O C CH3
+ H2O
b. _______ +
[H]
 3-methylpentan-2-ol (3 marks)
O
OH
CH3 C CH CH2 CH3
+ [H] →
CH3
CH3 CH CH CH2 CH3
CH3
3-methylpentan-2-one
Part C: Short Answer (8 marks)
5.
What is wrong with the following names? Write the correct name. (2 marks each)
a. 4,4-dimethylpentanal
- fun group must have lowest #
 2,2-dimethylpentanal
CH3 O
CH3 CH2 CH2 C C
CH H
3
O
b. N-ethyl butanamide
C CH3
- ethyl group has double bond O
 N-butyl ethanamide
6.
CH3 CH2 CH2 CH2 N
H
Which compound in more soluble in benzene (a non-polar solvent), propane or 1propanol? Explain your choice. (2 marks)
- propane is more soluble because it is non-polar
 it dissolves better in a non-polar solvent
(like dissolves like)
7.
Which compound will have the higher boiling point, 2-butanol or ethoxyethane?
Justify your answer. (2 marks)
ethoxyethane
is polar, but it can’t do H-bonding.
CH3 CH2 O CH2 CH3
can do H-bonding.  it has stronger intermolecular forces
 it requires more energy to separate
CH3 CH2 CH CH3
 it has a higher boiling point.
Butan-2-ol
OH