EXPERIMENT 7: REACTIONS OF ALDEHYDES AND KETONES

APPARATUS AND MATERIAL

Chemical: Pure samples of ethanal and propanone, 10 cm3; 40% aqueous solutions of methanal,
ethanal and propanone, 10 cm3; potassium dichromate solution, 1 cm3; Fehlings solution A and B, 3
cm3; saturated sodium hydrogensulphite solution, 3 cm3; Schiff reagent, 1 cm3; chlorine water, 1
cm3; 2,4-dinitrophenylhydrazine reagent, 10 cm3; iodine in aqueous potassium iodide solution 5
cm3; common laboratory reagents.
Apparatus: Test tubes; hard glass test tube; teat pipette; Bunsen burner; watch glass.
INTRODUCTION
Aldehyde and keotne contain the carbonyl group which has polar character because of the different
in electronegativity of the carbon and oxygen.
1. Bearing in mind the mechanism of addition to the unsaturated carbonyl group, predict the
relative reactivity of methanal, ethanal and propanone.
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2. Predict the relative ease of oxidation of methanal, ethanal and propanone
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PROCEDURE
(A) OXIDATION OF CARBONYL COMPOUNDS
*** Use aqueous solutions of the carbonyl compounds unless otherwise instructed.***
a. With acidified potassium dichromate solution:
Add 5 drops of each of the carbonyl compounds in turn to 2 drops of potassium dichromate
solution and 10 drops of dilute sulphuric acid in the test tube. Record your observations.
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b. With Tollens Reagent:
To 10 drops of silver nitrate solution in a CLEAN test tube. Add 1 drop of sodium hydroxide
followed by drops of dilute ammonia solution until the precipitate just redissolves. Add 5 drops
of each carbonyl compound to separated samples and warm the resulting solution in a beaker of
hot water. Record your observations.
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3. What species are present in Tollens Reagent? Explain how they are formed.
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c. With Fehlings solution:
Mix 10 drops of Fehlings solution A with an equal volume of Felhings solution B and add 5
drops of each carbonyl compound in turn. Warm the mixture gently. Record your observations
and try to explain.
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4. Fehlings test if used to detect sugar in the urine of people suffering from diabetes. Why do you
think sugars can be detected in this way?
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(B) ADDITION REACTIONS
a.
Addition of sodium hydrogensulphite:
To about 1 cm3 of saturate sodium hydrogensulphite solution add about 0.5 cm 3 of each
carbonyl compound in ture (use pure ethanal and propanone rather than aqueous solutions).
Cool each tube under the tap and record your observations.
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b. Reaction with Schiffs reagent:
Schiffs Reagent is a magenta dye decolourized by sulphur dioxide. The magenta colour would
be restored if the sulphur dioxide is removed. Try boiling a few drops of Schiffs reagent and
explain what happens.
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Now add a few drops of Schiffs reagent to each carbonyl compound in turn and explain what
happens.
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( C ) Condensation reactions
Carbonyl compounds undergo condensation reactions with hydroxylamine, hydrazine and
phenylhydrazine, but these are of little use in identifying the first few members of the
aldehyde and ketone series.
5. What feature have these reagents in common? Use this to explain the mechanism of these
condensation reactions.
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6. The most useful reagent for the identification of early members of the aldehyde and ketone
series is 2,4-dinitrophenylhydrazine. Explain thow this can be done. What advantage has it over
the simpler reagents mentioned above?
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Add 2 or 3 drops of each of the carbonyl compound, in turn, to about 3 cm3 of the solution of
2,4-dinitrophenylhydrazine in hydrochloric acid. Record your observations.
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7. Could this reaction be used as a general test for carbonyl compounds ? Explain
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(D) IODOFORM REACTION
To 5 drops of each carbonyl compound, in turn, add about 1 cm3 of a solution of iodine in aqueous
potassium iodide, followed by sodium hydroxide solution added dropwise until the colour of the
iodine is removed. Warm, if necessary, and note the smell and appearance of the mixtures.
8.

Which of the carbonyl compound have produced iodoform ?

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9.

Which functional group must present for this test to be positive?

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10. Make a list of reactions you could use to distinguish between:

(a)
methanal and ethanal
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(b) ethanal and propanone
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(b)
aldehydes and ketones in general
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