Experiment Six - Pre-Lab
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Experiment Six – Identification of an Unknown Aldehyde or Ketone
XXXXX
University of South Carolina
CHEM 332L-016
TA: March 14, 2023
Purpose/Objective
The purpose of this lab is to prepare a semicarbazone derivative and a 2,4-
dinitrophenylhydrazone (2,4-DNP) derivative of unknown aldehydes or ketones, recrystallize them, and determine their melting point. Through this process, the identity of the unknown substances can be determined. Introduction
Carbonyl compounds are sp
2
hybridized and trigonal planar with bond angles of 120°. A carbonyl group is relatively uncrowded, but as the alkyl groups around the carbonyl carbon increases, the reactivity of the carbonyl compound decreases. Since oxygen is more electronegative than carbon, oxygen has a greater share of the double bond’s electrons making the carbonyl group polar. Meaning the carbon is an electrophile, electron-deficient, which is subject to a nucleophilic attack. Reactions of carbonyl compounds are mostly acid catalyzed. Through this reaction, the acid will protonate the electronegative oxygen to form a carbocation, which is more susceptible to nucleophilic addition. All reactions are reversible because either of the two atoms with a lone pair attached to the tetrahedral carbon can be protonated and therefore eliminated. The reactions can be acid catalyzed with a controlled pH of 4.5. Derivatives are able to provide a solution by creating a solid for analysis and the solid derivative should be safe, easy to make, has a sharp melting point, and should be stable to hydrolysis. Imines, where the nitrogen atom carries an electronegative group that has a lone pair of electrons, are usually stable. This is due to the electronegative substituent that can participate in the delocalization of the imine double bond. The delocalization decreases the small positive charge on the carbon atom of the imine bond makes it less susceptible to nucleophilic attack. 2,4-
dinitrophenylhydrazine dissolved in EtOH/H
3
PO
4
will form a solid 2,4-dinitrophenylhydrazone when an aldehyde or ketone is reacted with it. Reaction Schemes/Structures
2,4-DNP Semicarbazide hydrochloride Reagents
Name,
Structure,
MW (g/mol)
Melting
°C
Boiling
°C
Density
g/mL
Properties
2,4-DNP
Derivative
(MP)
Semicarb
Derivative
(MP)
Benzaldehyde C
7
H
6
O 106.12
-26
178-
179
1.045
Flammable
liquid; Cherry-
like scent 237 °C
216 °C
3-Heptanone
C
7
H
14
O 114.18
-39
147
0.818
Colorless liquid
with a mild
fruity odor;
slightly soluble
81 °C
101 °C
Acetophenone
C
8
H
8
O 120.15
19.6
202
1.03
Colorless liquid
but solid at
lower
temperatures
238 °C
198 °C
Diethyl ketone
C
5
H
10
O
86.1334
-42
101
0.814
Flammable
liquid 156 °C
138 °C
Cyclohexanon
e
-47
155
0.947
Flammable
liquid oily, white
to slightly
yellow liquid
with a
peppermint-like
162 °C
166 °C
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C
6
H
10
O
98.1444
odor Name,
Structure, MW
(g/mol)
Melting
°C
Boiling
°C
Densit
y g/mL
Properties
Safety
Phosphoric acid
H
3
PO
4
97.99506
21
158
1.685
Viscous,
colorless,
odorless,
liquid;
solidifies at 70
°F hygroscopic
Corrosive to tissue and
irritating to the skin,
mucous membranes,
upper respiratory tract
and eyes; fatal if
swallowed
Ethanol
C
2
H
5
OH 32.042
-114.1
78.3
0.789
Colorless
liquid; pleasant
alcoholic odor
Harmful by ingestion,
inhalation, or skin
absorption; irritant or the
eyes, nose, throat, and
skin (flashback along the
vapor trail may occur)
Methanol
CH
3
OH 32.042
-98
64.6
0.791
Colorless
liquid with a
characteristic
pungent odor
May cause severe skin
and eye irritation; it can
be absorbed through the
skin; it may cause
narcosis
Pyridine
C
5
H
5
N 79.1012
-41.6
115.2
0.9819
Colorless or
yellow liquid
with a
penetrating
sickening
stench
Toxic by ingestion,
inhalation and contact of
the skin, eyes, and
respiratory tract; NH
3
may cause sterility in
males
2,4-DNP
C
6
H
6
N
4
O
4
198.1378
198
-
-
Flammable
liquid; orange
crystals with
ammonia-like
odor
May cause eye irritation;
Flammable; Possible
mutagen
Semicarbazide
hydrochloride CH
6
ClN
3
O
175-177
~185
-
Very soluble in
water; white
crystals Toxic; local irritant
111.53309
Procedure
1.
Obtain 1 mL of the unknown from the hood and record the number. 0.5 mL will be used for the semicarbazide test and 0.5 mL will be used for the 2,4-DNP test.
Preparation of 2,4-DNP Derivative (Brady’s Reagent):
1.
From the fume hood acquire 2 mL of the 2,4-DNP stock solution and place it in a medium test tube
2.
Add 0.5 mL of the unknown compound to the test tube 3.
Place a beaker 2/3 full of water with a thermometer on the hot plate. Make sure that the thermometer is not touching the bottom of the beaker. Make sure that the temperature maintains 60-65 °C
4.
Heat the mixture 5-10 minutes in the warm water bath
5.
Remove the test tube from the water bath and cool the mixture to room temperature (10-
15 minutes) to begin crystallization. Place the test tube in an ice bath until crystallization is complete. If needed scratch the inside of the test tube with a glass stirring rod to induce
crystallization
6.
Use suction filtration to isolate the solid product. Wash the solid product with 1 mL ice-
cold water dropwise
7.
Transfer the product to a small test tube and rescrystallize as follows:
a.
Cover the crude 2,4-DNP derivative in the test tube with a small amount of warm ethanol b.
Gently heat while agitating on the water bath
c.
Slowly add ethanol dropwise until all the solid has dissolved
d.
NOTE: some soluble and/or insoluble impurities may not dissolve regardless proceed to Step 9
8.
Slowly cool the hot solution to room temperature, then place it in an ice bath to complete the crystallization
9.
Use suction filtration to isolate the solid. Use 1 mL of ice-cold ethanol to wash the product 10. Collect the pure product, dry, and determine the melting point
Preparation of Semicarbazone Derivative:
1.
In a medium test tube, place 0.5 mL of stock semicarbazide hydrochloride solution
2.
Add 0.5 mL of the unknown compound and 1-2 mL of methanol
3.
Add 10 drops of pyridine. Warm the solution gently in the warm water bath for 8-10 minutes
4.
Slowly cool the solution in the test tube to room temperature. Place the test tube in an ice bath to complete the crystallization. Scratch the inside of the rube with a glass rod to induce crystallization if needed
5.
Use suction filtration to isolate the cool mixture and collect the crude solid product 6.
Use 10 drops of ice-cold water followed by 5 drops of ice-cold methanol to wash the crude product
7.
Recrystallize the crude product from methanol using steps 8-9 of the 2,4-DNP derivative
8.
Use suction filtration to collect the pure product, allow the product to air dry and determine the melting point Waste Reagent Disposal
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Excess aqueous solutions should be washed down the drain with excess water. Dispose of the 2,4-DNP filtrate liquid into the organic liquid waste container. Aldehyde/ketone derivatives should be disposed of in the solid organic waste container. Soiled gloves and paper towels must be disposed of in proper containers. Broken glass is to be disposed of in the broken glass container.
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