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ALDEHYDES AND KETONES

J.V. DE GUZMAN
DEPARTMENT OF CHEMICAL ENGINEERING, COLLEGE OF ENGINEERING
UNIVERSITY OF THE PHILIPPINES, DILIMAN QUEZON CITY, PHILIPPINES
DATE PERFORMED: MARCH 20, 2015
INSTRUCTORS NAME: ALLAN KENNETH REGUNTON

ANSWERS TO QUESTIONS
1. Give the reactions for all tests which yield positive results.
A. 2,4-dinitrophenylhydrazine

Acetone:

Benzaldehyde:
B. Schiffs Test

+ H2O

+ H2O

HO3Schiffs
S
Reagent
Rosaline hydrochloride

Formaldehyde:

+ HO3SDark purple

Benzaldehyde:

+ HO3SHot pink

C. Benedicts Test
Formaldehyde:
+ Cu2O(s) + 3H2O

+ 2Cu

+ 5OH-

D. Iodoform Test
1

Acetone:

+ 3I2 + 4NaOH

+ CHI3(s) + 3NaI + 3H2O


Iodoform: yellow ppt

Ethanol:

+ I2 + 2NaOH

+ 2NaI + 2H2O

+ 3I2 + 4NaOH

+ CHI3(s) + 3NaI + 3H2O

Iodoform: yellow ppt

2. Differentiate the following pair of compounds. Indicate the reagent and


the expected visible result/s.
a.

and
(3-hexanone and 2-hexanone) - Both are
ketones but they differ on the alkyl substituent attached to each of
them. The first one, 3-hexanone, has an ethyl and propyl substituent
while the second one, 2-hexanone, has a methyl and butyl substituent.
Therefore, the two can be differentiated using the iodoform test using
I2 in KI and NaOH as the reagent. The second ketone has a methyl
substituent thus it will react with the warm reagent to yield a yellow
precipitate or iodorm while the second one will show no visible results
under the iodoform test.

b.

and
(2-hydroxypropanal and 3-hydroxy-pent-1-one) The first one has an aldehyde functional group while the second one
has a ketone group. Thus, to differentiate the two, they can be
subjected under Schiffs test since the Schiffs reagent only reacts with
an aldehyde. The ketone will show no visible results under the Schiffs
reagent but the aldehyde, 2-hydroxypropanal, will yield a dark purple
solution.

c.

and
(hep-3-methyl-2-one and hep-3-methyl-2-ol)the first compound is a ketone while the second one has an alcohol as
its functional group. To differentiate the two, 2,4-DNPH can be used
since it shows no visible result upon reaction with alcohols but gives a
positive test result for ketones indicated by the formation of yellow
precipitate.

d. 2-hexanone and 3-pentanone (


and
)- These two ketones
again differ on their substituents. The first one, 2-hexanone has a
2

methyl and butyl substituents while 3-pentanone has both ethyl


substituents. Thus, 2-hexanone can give a positive test result if reacted
with I2 in KI and NaOH because of a methyl group attached to it to yield
an iodoform or yellow precipitate. On the other hand, 3-pentanone will
show no visible results under the iodoform test since the test applies
only for ketones with a methyl substituent.

e.

and
(Benzaldehyde and 1-benzylpropanal)- Both are
aldehydes with an aromatic ring, however, 1-benzylpropanal has an
aliphatic group. Thus, they can be subjected under the Benedicts test
since it only gives positive test result for aliphatic aldehydes. When
reacted with the Benedicts reagent, benzaldehyde will show no visible
result while 1-benzylpropanal will decolorize the blue Benedicts
reagent and form a brick red precipitate or Cu2O.

3. Discuss briefly the effect of acid concentration on the rate of addition


or formation of precipitate with 2,4-DNPH in part E.

Shown above is the mechanism of the reaction of 2,4-DNPH with


acetone. The first two steps lead to the formation of carbinolamine
while the last three show the dehydration of the carbinolamine to
imine. Note that Step 4 is the key in the dehydration phase and is thus
the rate determining step. However, step 4 is highly dependent on the
pH of the solution and too high pH of the medium solution decreases
its rate. However, if the reaction is carried out in a very acidic medium,
amine in Step 1 can be protonated and will be transformed into an
unreactive quaternary ammonium form. Thus, the optimum pH of the
solution is usually around 5 where the reaction rate is maximum. Thus,
on part E of the experiment, the rate reaction of 2,4-DNPH with
acetone gives the following result:
(arranged in increasing rate): 0.05 M HCl < 0.02 M HCl < 0.02 M
CH3COOH
The formation of a yellow precipitate, an indication of the reaction, is seen
fastest in 0.02 M CH3COOH (pH= 3.2) because its the pH nearest the optimal
pH. However, as the pH decreases and became very near to 1, the rate of
3

reaction also decreases as observed in the reaction carried in 0.02 M HCl


(pH=1.7) and 0.05 M HCl (pH=1.3) because the reagent, 2,4-DNPH may have
been protonated to an unreactive quaternary ammonium form.
REFERENCES:
[1] Clark, J. Addition-Elimination Reactions of Ketones and Aldehydes.
Chemguide.
[Online].
2004.
Retrieved
from:
http://www.chemguide.co.uk/organicprops/carbonyls/addelim.html (accessed
March 24, 2015).
[2] Carey, F. A. 2006. Organic Chemistry 6th ed. Chapter 17: Aldehydes and
Ketones: Nucleophilic Addition to the Carbonyl group. The McGraw-Hill
Companies: New York.

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