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Aldehydes and Ketones

ANSWERS TO QUESTIONS

1. Give the chemical reactions for all the tests that gave positive results.
a. 2,4-DNPH
 Acetone

NHNH 2 N
O
O 2N NH
+
O 2N NO 2
NO 2
 Benzaldehyde
NHNH 2 N
O O 2N NH
+
O 2N NO 2
NO 2
b. KMnO4
 Formalin
O KMnO4 O

H H H OH

 Benzaldehyde
OH
O
KMnO4

c. Fehling’s test
 Formalin
O O
+ 2Cu2+ + H2O + Cu2O + 2H+
H H H OH

d. Iodoform test
 Acetone
O OH-, I2, KI O

–
+ CHI3
O

 Ethanol
[O] O OH-, I2, KI O
OH
–
+ CHI3
O

2. Indicate the reagent that would differentiate the following pairs of compounds and give the expected visible
result/s.

Compound 1 Compound 2 Reagent Expected result

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Compound 2: yellow
I2 in KI, NaOH
precipitate
Compound 1: brown
KMnO4
precipitate
Compound 1: brick red
Fehling’s solution
precipitate
Compound 2: yellow
I2 in KI, NaOH
precipitate

Compound 1: orange
2,4-DNPH
precipitate

Compound 1: yellow
2-hexanone 3-pentanone I2 in KI, NaOH
precipitate

Compound 2: Brick red

Fehling’s solution
precipitate

3. Discuss briefly the effect of acid concentration on the rate of addition or formation of precipitate with 2,4-DNPH
in part E.
The acid acts as a catalyst by positively charging the carbonyl carbon with H + ions, thus increasing its
reactivity with a nucleophile (2,4-DNPH), thus speeding up the reaction. Differences in acid strength have
varying rates of reaction. A strong acid, such as HCl, gives a faster reaction than a weak acid, such as CH3COOH,
due to its higher concentration of H+ ions. A strong acid can also neutralize the nucleophile at high
concentrations, which would hinder the reaction.

References
[1] Bicking, M. L.; Cooke, W. M.; Kawahara, F. K.; Longbottom, J. E. Effect of PH on the Reaction of 2,4-
Dinitrophenylhydrazine with Formaldehyde and Acetaldehyde. J. Chromatogr. A 1988, 310–315.