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Organic Problem Solving
1. Suggest a way (either physical or chemical) to distinguish between ethanol and
methoxymethane.
2. Compound A, oI Iormula C
2
H
6
O
,
is oxidized to compound B oI Iormula C
2
H
4
O. B is
Iurther oxidized to compound C oI Iormula C
2
H
4
O
2
. C reacts with A to produce a
compound D oI Iormula C
4
H
8
O
2
. Give the names oI structures A, B, C, and D, explain
your reasoning, and write out one oI the mechanisms.
3. A compound oI Iormula C
3
H
8
O exists as two isomers, A and B. With a strong oxidizing
agent, A Iorms a compound C oI Iormula C
3
H
6
O, while B Iorms compound D oI
Iormula C
3
H
6
O
2
. D turns blue litmus red. Give names and structures oI the Iour
compounds, linking compounds that are related.
4. The compounds butanone, 1-butanol, ethoxyethane, and butane have boiling points oI
272 K, 307 K, 352 K and 390 K, though not in that order. Match the compound with the
boiling points, explaining your reasoning.
5. Discuss the chemical reagents and reaction conditions necessary to complete each oI the
three steps in the reaction sequence shown below.
step 1 step 2 step 3
CH
3
CHCH
2
-------~ CH
3
CHCH
3
------~ CH
3
-C-CH
3
------~ CH
3
CHCH
3
, // ,
OH O OH
6. An aliphatic compound, X, is known to have a molecular Iormula C
4
H
10
O.
a) Compound X reacts with sodium metal to produce hydrogen gas. To what class oI
compounds may compound X be assigned? Write 3 possible structural Iormulae Ior
compound X.
b) Dehydration oI compound X by hot, concentrated sulphuric acid yields a gaseous
compound, Z, oI Iormula C
4
H
8
. Write a balanced equation which describes this
process. (IB exam 1993)
7. Compound A, C
3
H
6
O, is a liquid which reacts with an oxidizing agent such as
Cr
2
O
7

-2
and is thereby oxidized to B, C
3
H
6
O
2
, a strongly smelling liquid.
Compound A also reacts with LiAlH
4
(a strong reducing agent) to Iorm compound C,
C
3
H
8
O. This is easily dehydrated to give a gas, C
3
H
6
, which reacts with hydrogen
bromide to Iorm D.
The compounds B and C react together in the presence oI concentrated H
2
SO
4

(aq)
to Iorm
E, C
6
H
12
O
2
, a liquid with a pleasant, Iruity smell.
Write structural Iormulae and names Ior the compounds A, B, C, D and E.
(IB exam 1991).
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8. When pentan-2-ol and pentan-3-ol are each heated with a n acidiIied solution oI
potassium permanganate (VII), the colour oI the solution changes Irom purple to nearly
colourless.
a) What is the oxidation stated oI the manganese product?
b) Name another reagent which would have the same eIIect upon the alcohols as
potassium permanganate (VII)
c) Draw the structural Iormulae oI the two alcohols and the products oI their reactions
with potassium permanganate (VII). (IB exam 1990).
9. The chemical Iormula C
2
H
6
O has two isomers. Draw each isomer and identiIy the
Iunctional group in each case. Predict how the boiling points and solubility in water
will diIIer. Explain the basis Ior your predictions.
10. Predict the reagents (3) necessary to produce the Iollowing:
a) methylmethanoate
b) ethylbutanoate
c) propylethanoate
11. Liquid A on standing with silver nitrate solution gives a cream precipitate and a solution
oI B. When B is boiled with concentrated sulphuric acid, it gives a colourless gas C.
C reacts with bromine to give a liquid D which o boiling with hot, concentrated, alcoholic
sodium hydroxide gives a gas E. E reacts with an oxidising agent such as acidiIied
KMnO
4
/OH
-1
, to Iorm ethan-1,2-dioic acid, (aka: oxalic acid). II a contains two carbon atoms,
identiIy A to E, explain your reasoning and write equations Ior all the reactions occurring.
12. A solid P burns with a very smoky Ilame and a solution oI P is very slightly basic. When a
solution oI P in water is treated with bromine water, a white precipitate, Q, Iorms. When
P is treated with concentrated nitric acid a yellow solid, R Iorms. IdentiIy P, Q, and R and
give equations Ior the reactions.
13. Show by means oI equations and essential reaction conditions only, how you would carry out
the Iollowing transIormations, (using reactions you have already met):
(a) H
2
C CH
2
into CH
3
CH
2
CH
2
OH
(b) CH
3
CH
2
OH into (OH)CH
2
CH
2
(OH)
(c) C
6
H
6
into C
6
H
5
Cl
(d) C
6
H
6
into C
6
H
5
COOH