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CHEM 2425-85201
Preparation of Carbocations by the Friedel-Crafts Reaction
INTRODUCTION
Friedel-Crafts alkylation is an important method for adding alkyl chains to aromatic rings
through the use of a strong Lewis acid, generally AlCl3 or FeCl3, as a catalyst. Though the
reaction has some limitations (namely the potential for carbocation rearrangement limiting the
types of alkyl chains that can be substituted), its relative simplicity makes it an important tool
when identify aromatic compound in this experiment. In Friedel-Crafts reaction,
tricholoromethane (CHCl3, chloroform) reacts with three molecules of the aromatic hydrocarbon
to form a triarylmethane. The more conjugated the compound, the more visible the color that it
has. The triarylmethane will lose a hydride ion to one of several different carbocation
intermediates, yielding a colored triarylmethyl carbocation (light yellow). The substitution
reactions as below:
A lC l3

A rH + C H C l3
3 A r H + C H C l3
A r3C H + R

A lC l3

A rC H

+ H C l

A r3C H + 3 H C l
A r3C

+ R H (R

= A r2C H + , e tc .)

PROCEDURE
Add a drop of an aqueous compound or 20mg of solid into the labeled test tube:

Test Tube (TT)

Step

Add 1 drop

Toluene

Limonene

Naphthalen

Anthracen

Biphenyl

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Under the hood, add 8 drops

chlorofor

chlorofor

chloroform

chloroform

Chlorofor
m

Prepare in 13x100-mm test tube (need to be clean, dry):

Measure carefully 0.10g of anhydrous AlCl3 into the test tube. Heat the test tube gently
over a burner flame until it forms a thin layer of sublimed solid up the sides of the tube. While it
is still hot, pipet the test tube #1 to #5 down one side that is coated with the white solid. Each
time, applying the remaining solutions to fresh areas of the sublimed solid.
DISCUSSION
If the compound is aromatic, the reaction on the surface of the sublimed layer gives the
visible color. The original procedure said pipetting the test tubes when it is cool. The first and
second observation was done based on the original procedure; by that, the test tubes are pipetting
when it is already cool. This procedure gives wrong interpretation because limonene and
anthracene gives no visible color; other compounds give very light yellow colors.
The third observed colors of each test tubes were red-orange for test tube 1; no color for
test tube 2; dark brown for test tube 3; greenish for test tube 4; dark blue for test tube 5. The
third observation was done while the test tubes are still hot. Therefore, limonene is not an
aromatic compound; toluene, naphthalene, anthracene, and biphenyl are aromatic compounds.
CONCLUSION
The experiments procedure was as simple as the mechanism of the substitution reaction
of an aromatic ring. The visible color appears whenever the aromatic compound reacts with
chloroform with presence of the catalyst AlCl3. However, the original procedure did not give

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good observation. Therefore, the procedure needs to put the age and the quality of the catalyst,
AlCl3, into its consideration.
EXERCISE
17-17 Predict the products of the reactions
(a) (excess) benzene + isobutyl chloride + AlCl3
CH3
H

Cl

H3C

a fte r C l- le a v e , th e
re a rra n g e m e n t h a p p e n s ,
p r im a r y c a r b o c a tio n
re a rra n g e d to s e c o n d a ry
c a rb o c a tio n , w h ic h is
m o r e s ta b le .

CH3

A lC l3

CH3
H3C

(b) (excess) toluene + butan-1-ol + BF3

CH3

CH3

CH3

HO

CH3

BF

CH3
CH3

( o r th o , p a r a - d ir e c tin g )
CH3

H3C

(p a ra )

(c) (excess) nitrobenzene + 2-chloropropane + AlCl3

O
+

Cl

A lC l3
H3C

CH3

N o re a c tio n b e c a u s e
n itr o b e n z e n e is to o
d e a c tiv a te d .

(d) (excess) benzene + 3,3-dimethylbut-1-ene + HF

(o rth o )

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HF

CH3

H3C
H2C

CH3

H3C

CH3
CH3
CH3

M e th y l s h ift h a p p e n s .
R e a rra n g e d .