EXP VIDEO https://www.youtube.com/watch?v=9Wxxv7kwXlA&list=PLE-217H0ao60Uzpzj-FNP_0ScVp5SZB7j&index=81.Pre lab questionWhat are the functional groups in your substrate?-Nitrate-Nitrate and acetate-Amide and ether-Benzene ringb.The stable reaction intermediate in this reaction isNitronium ionBenzonium ionCarbocationCarbanionc.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 activatoreThe catalyst in this experiment was-Glacial acetic acid-Nitric acid-Sulfuric acid-EthanolfThe 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-NitrophenacetinH What is the theoretical yield of this experiment?-1.217g-49%-4.9g-.0893gI The recrystalization solvent in this reaction was-Water-Ethanol-50:50 water : Ethanol-Cold water. Experiment 22Nitration of PhenacetinPURPOSETo nitrate phenacetin via electrophilic aromatic substitution.LEARNING OBJECTIVESStudents will learn to:perform nitration via electrophilic aromatic substitution• safely work with concentrated nitric and acetic acidsREADING ASSIGNMENTPlease read the following material in "Laboratory Techniques in Organic Chemistry" (4t ed.) byMohrig, et al:• Sections 5.1-5.3- Recrystallization• Sections 14.2, 14.3- Melting points and Melting Point RangesBACKGROUND AND DISCUSSIONBelow is the balanced equation for nitration of phenacetin.cat. HOACHNO,H,0NO,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 anitronium ion.HNO, + HOAC NO, + "OAc + H,OTraditionally sulfuric acid and nitric acid are mixed to form the nitonium ion. In thisparticular experiment, the use of acetic acid gives better results.Austin Community College CHEM 2125 – Organic Chemistry II LabOnce the nitronium ion is formed, it reacts with phenacetin by the followingmechanism. NON,HNO,benzonium ian(resonance hybrid)The intermediate benzonium ion is resonance-stabilized. Another product is possible from thisreaction, 3-nitrophenacetin. This product is not formed by this procedure. The location of thenitro 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 acetamidegroup is considered more strongly activating. As a result, the nitro ends up ortho to thisgroup.TABLE OF PROPERTIESCompoundMM (g/mol)mp (°C)phenacetin1791352-nitrophenacetin2441033-nitrophenacetin244125SAFETY INFORMATIONBoth nitric acid and acetic acid are hazardous. Wear appropriate safety equipment,including gloves when working with these chemicals. Only use these acids in well ventilatedareas and wash with plenty of water immediately if you get any on your skin or clothing.PROCEDUREDissolve 5.00 mmol phenacetin in 20 mL of glacial (17.4 M) acetic acid in a 125-mLErlenmeyer flask. Add a stir bar and set on a stirring hot plate. Turn on the stirring mechanismwait for complete dissolutiNext, carefully add 1.0 mL of concer(15.8 M) nitricacid2dropwise to the stirring solution. Turn the heating element on to about 40% and heat for 10minutes. Alternately, the sample can be heated in a hot water bath at 80 °C for the 10 minutes.

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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.

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.

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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