Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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EXP VIDEO
https://www.youtube.com/watch?v=9Wxxv7kwXlA&list=PLE-217H0ao60Uzpzj-FNP_0ScVp5SZB7j&index=8
1.Pre lab question
- What are the
functional groups in your substrate?
-Nitrate
-Nitrate and acetate
-Amide and ether
-Benzene ring
b.The stable reaction intermediate in this reaction is
Nitronium ion
Benzonium ion
Carbocation
Carbanion
c.How would you distinguish between 2-nitrophenacetin and 3-nitrophenacetin?
-Color difference
-Melting point difference
-Difference in Molecular weight
-They cannot be differentiated.
dAn ether group is
-Ortho para activating
-Meta activating
-Ortho para deactivating
-ring activator
eThe catalyst in this experiment was
-Glacial acetic acid
-Nitric acid
-Sulfuric acid
-Ethanol
fThe chemical waste from this experiment should be discarded in the
-Sink
-Halogenated waste container
-non-halogenated waste container
-Heavy metal waste container.
gWhat is the limiting reagent in this experiment?
-Nitric acid
-Glacial acetic acid
-Phenacetin
-Nitrophenacetin
H What is the theoretical yield of this experiment?
-1.217g
-49%
-4.9g
-.0893g
I The recrystalization solvent in this reaction was
-Water
-Ethanol
-50:50 water : Ethanol
-Cold water.
Transcribed Image Text:Experiment 22
Nitration of Phenacetin
PURPOSE
To nitrate phenacetin via electrophilic aromatic substitution.
LEARNING OBJECTIVES
Students will learn to:
perform nitration via electrophilic aromatic substitution
• safely work with concentrated nitric and acetic acids
READING ASSIGNMENT
Please read the following material in "Laboratory Techniques in Organic Chemistry" (4t ed.) by
Mohrig, et al:
• Sections 5.1-5.3- Recrystallization
• Sections 14.2, 14.3- Melting points and Melting Point Ranges
BACKGROUND AND DISCUSSION
Below is the balanced equation for nitration of phenacetin.
cat. HOAC
HNO,
H,0
NO,
The mechanism of this reaction is called electrophilic aromatic substitution
(EAS). In the first step of the mechanism nitric acid and acetic acid react to form a
nitronium ion.
HNO, + HOAC NO, + "OAc + H,O
Traditionally sulfuric acid and nitric acid are mixed to form the nitonium ion. In this
particular experiment, the use of acetic acid gives better results.
Austin Community College CHEM 2125 – Organic Chemistry II Lab
Once the nitronium ion is formed, it reacts with phenacetin by the following
mechanism.
Transcribed Image Text:NON,
H
NO,
benzonium ian
(resonance hybrid)
The intermediate benzonium ion is resonance-stabilized. Another product is possible from this
reaction, 3-nitrophenacetin. This product is not formed by this procedure. The location of the
nitro group in the final product depends upon the substituents already on the ring. Both
-NHAC and -OEt are considered activating, ortho-para directors. However, the acetamide
group is considered more strongly activating. As a result, the nitro ends up ortho to this
group.
TABLE OF PROPERTIES
Compound
MM (g/mol)
mp (°C)
phenacetin
179
135
2-nitrophenacetin
244
103
3-nitrophenacetin
244
125
SAFETY INFORMATION
Both nitric acid and acetic acid are hazardous. Wear appropriate safety equipment,
including gloves when working with these chemicals. Only use these acids in well ventilated
areas and wash with plenty of water immediately if you get any on your skin or clothing.
PROCEDURE
Dissolve 5.00 mmol phenacetin in 20 mL of glacial (17.4 M) acetic acid in a 125-mL
Erlenmeyer flask. Add a stir bar and set on a stirring hot plate. Turn on the stirring mechanism
wait for complete dissoluti
Next, carefully add 1.0 mL of concer
(15.8 M) nitric
acid
2
dropwise to the stirring solution. Turn the heating element on to about 40% and heat for 10
minutes. Alternately, the sample can be heated in a hot water bath at 80 °C for the 10 minutes.
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