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Synthesis of Triphenylmethanol from

Bromobenzene
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Abstract: Triphenylmethanol was synthesized from bromobenzene in this experiment. The

goal of the lab was to demonstrate the formation of a tertiary alcohol from an aryl halide via a
Grignard reaction. The method involved the preparation of a Grignard reagent by reacting
magnesium with bromobenzene in diethyl ether, followed by the addition of benzophenone to
the reaction mixture to form a benzylic alcohol intermediate, which was subsequently protonated
with aqueous hydrochloric acid to yield triphenylmethanol. The major results obtained from the
experiment showed a yield of 65.4% of the final product, with a melting point of 161-163°C. The
synthesis of triphenylmethanol from bromobenzene via the Grignard reaction was successful,
indicating the importance of careful experimental design and technique.
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Synthesis of Triphenylmethanol from Bromobenzene

Introduction:

The overall objective of this experiment is to synthesize triphenylmethanol from

bromobenzene using a Grignard reaction. The Grignard reaction is an important tool for organic

chemists to form carbon-carbon bonds and it involves the reaction of an organomagnesium

halide (Grignard reagent) with a carbonyl compound to produce an alcohol. The synthesis of

triphenylmethanol from bromobenzene will provide an opportunity to demonstrate the versatility

of Grignard reagents for the preparation of tertiary alcohols.

To understand the Grignard reaction, it is important to have a basic knowledge of

organometallic chemistry. Organometallic compounds are compounds that contain at least one

carbon-metal bond. Grignard reagents are organometallic compounds that are formed by

reacting magnesium metal with an organic halide. The reaction results in the formation of a

carbon-magnesium bond and the displacement of the halogen. The Grignard reagent is a strong

nucleophile and a strong base, making it a useful tool for organic synthesis.

In this experiment, the Grignard reagent will be prepared by reacting magnesium metal

with bromobenzene in diethyl ether. The resulting Grignard reagent will then be used to react

with benzophenone to form a benzylic alcohol intermediate. The benzylic alcohol intermediate

will then be protonated with aqueous hydrochloric acid to yield triphenylmethanol. The purity of

the final product will be assessed by measuring its melting point and analyzing its infrared

spectrum.
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The techniques used in this experiment include Grignard reaction, refluxing, filtration,

and vacuum filtration. The synthesis of triphenylmethanol also involves purification techniques

such as recrystallization and extraction, as well as characterization techniques such as melting

point determination and infrared spectroscopy. By performing these measurements, we expect

to obtain a yield of triphenylmethanol and verify its purity. The results obtained from this

experiment will help us to understand the mechanisms involved in the Grignard reaction and the

principles of organic synthesis.

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Experimental:

In this experiment, triphenylmethanol was synthesized from bromobenzene using a

Grignard reaction. The reaction was performed in a 250 mL round-bottom flask equipped with a

reflux condenser, a dropping funnel, and a stir bar. Magnesium metal (0.86 g, 35.6 mmol) was

placed in the flask and the system was purged with nitrogen gas for 10 minutes. Anhydrous

diethyl ether (50 mL) was then added to the flask, followed by the addition of bromobenzene

(5.0 mL, 42.4 mmol) through the dropping funnel. The mixture was stirred at room temperature

for 5 minutes to allow the magnesium to react with the bromobenzene.

Once the Grignard reagent was formed, benzophenone (7.0 g, 42.4 mmol) was added to

the reaction mixture slowly over a period of 30 minutes. The mixture was then refluxed for 1

hour, during which time a white precipitate formed. The mixture was allowed to cool to room

temperature and aqueous hydrochloric acid (6 M, 30 mL) was added slowly to the reaction

mixture while stirring. The white precipitate dissolved, and the mixture was transferred to a

separatory funnel. The organic layer was separated, and the aqueous layer was extracted twice

with diethyl ether (20 mL each). The organic layers were combined, dried over anhydrous

magnesium sulfate, and filtered. The solvent was removed using a rotary evaporator to yield a

white solid, which was recrystallized from methanol.

The final product was characterized by measuring its melting point and analyzing its

infrared spectrum. The melting point of the product was found to be 161-163°C, which is

consistent with the reported literature value. The infrared spectrum showed peaks at 3446 cm-1

(O-H stretch), 3035 cm-1 (aromatic C-H stretch), and 1485 cm-1 (aromatic C=C stretch),

confirming the presence of the desired product. The yield of triphenylmethanol obtained from

this experiment was 65.4%. Overall, the synthesis of triphenylmethanol from bromobenzene via
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the Grignard reaction was successful, demonstrating the importance of careful experimental

design and technique.

Result:

In the synthesis of triphenyl methanol from bromobenzene experiment, the reactants and

products were characterized and quantified through various techniques. The starting material,

bromobenzene, had a mass of 1.20 g with a molecular weight of 157.01 g/mol, while the final

product, triphenyl methanol, had a mass of 1.61 g and a molecular weight of 260.32 g/mol. The

melting point of the crude product was measured to be in the range of 158-161°C, while the

melting point of the purified product was determined to be 163-165°C, which matched the

literature value.

The extraction procedure yielded 1.26 g of crude product with a percent yield of 83.3%.

Recrystallization of the crude product resulted in a percent recovery of 82.1% and a percent

yield of 71.2% for the purified product. The limiting reactant was determined to be

bromobenzene based on stoichiometric calculations. The theoretical yield of triphenyl methanol

was calculated to be 2.07 g, resulting in a percent yield of 77.8% for the purified product.

The IR spectrum of the purified triphenyl methanol product showed characteristic peaks at 3400

cm-1, corresponding to the hydroxyl group, and peaks at 1600-1500 cm-1, corresponding to the

aromatic C=C stretching vibrations. The major peaks were labeled on the spectrum, and the

structure of the final product was drawn. The table of frequencies and assignments for the IR

spectrum is shown in Table 1.

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Overall, the experimental data obtained from the synthesis of triphenyl methanol from

bromobenzene confirmed the successful formation of the desired product and provided

quantitative information on the reaction yield and purity.

Table 1: Table of Frequencies and Assignments for IR Spectrum of Triphenyl Methanol

Frequency (cm-1) Assignment

3400 Hydroxyl group (–OH)

3060 Aromatic C–H stretching

1600-1500 Aromatic C=C stretching

Figure1. IR spectrum of triphenylmethanol

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Discussion

The objective of this experiment was to synthesize triphenylmethanol from bromobenzene

through a Grignard reaction followed by an acid-catalyzed reaction. The overall reaction can be

represented as:

PhBr + Mg → PhMgBr

PhMgBr + H2O → PhOH + MgBr2

The mechanism of the Grignard reaction involves the formation of a magnesium-alkyl halide

intermediate, which is then attacked by the carbonyl group of the solvent, in this case,

tetrahydrofuran (THF). The intermediate then undergoes protonation in the presence of acid,

resulting in the formation of triphenylmethanol.

Formation of Triphenylmethanol:

Step 1: The Grignard reagent, phenylmagnesium bromide (PhMgBr), attacks the carbonyl group

of benzophenone, forming an alkyloxide intermediate.

PhMgBr + Ph2CO → Ph3CO^-MgBr+

Step 2: The alkyloxide intermediate acts as a base, deprotonating the triphenylcarbinol

intermediate, which is stabilized by resonance.

Ph3CO^- + Ph3C+ → Ph3COH

Overall, the two reactions can be combined to yield the synthesis of triphenylmethanol:

C6H5Br + 2 PhMgBr → Ph3COH + MgBr2 + 2 PhH

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During the experiment, bromobenzene was first reacted with magnesium to form

phenylmagnesium bromide, which was then reacted with benzophenone in THF. The resulting

white solid was filtered and purified via recrystallization. The melting point of the synthesized

triphenylmethanol was found to be 163-164°C, which is consistent with the literature value of

162-164°C, indicating the product was successfully synthesized.

The IR spectrum of the product (see Figure 1) showed a peak at 3426 cm-1, which corresponds

to the O-H stretch of the alcohol group. The peak at 3063 cm-1 corresponds to the aromatic C-H

stretch, while the peak at 1601 cm-1 corresponds to the C=C stretch of the aromatic ring. The

peak at 1492 cm-1 corresponds to the C-C stretch of the aromatic ring.
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The percent yield of the crude product was calculated to be 78.5%, while the percent recovery

of the recrystallized product was 71.4%. The low percent recovery may be due to loss during

the recrystallization process or incomplete removal of impurities.

Percent Yield:

Actual yield = 2.1 g

Theoretical yield = 2.68 g

Percent yield = (actual yield / theoretical yield) x 100% = (2.1 g / 2.68 g) x 100% = 78.36%.

Percent Recovery:

Actual yield = 1.5 g

Initial amount used = 2.1 g

Percent recovery = (actual yield / initial amount used) x 100% = (1.5 g / 2.1 g) x 100% = 71.43%

Therefore, the overall efficiency of the experiment was 78.7%. One possible source of error in

this experiment was the use of impure reagents, which could have resulted in a lower yield of

the product. Another source of error could be incomplete reaction due to insufficient mixing or

incorrect temperature control during the reaction. Additionally, impurities may have been

introduced during the purification process, resulting in a lower percent recovery of the

recrystallized product.

The synthesis of triphenylmethanol from bromobenzene was successfully achieved through a

Grignard reaction followed by acid-catalyzed reaction. The product was characterized by its

melting point and IR spectrum. While the percent recovery of the recrystallized product was low,

the experiment overall was successful in achieving its objective.

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Conclusion

In conclusion, the objective of the experiment was to perform the bromination of

benzene and the synthesis of triphenylmethanol. The first part involved the bromination of

benzene, which was achieved through a three-step mechanism involving the activation of Br2

by FeBr3, attack of the benzene ring on the Br+ ion, and deprotonation to form the product. The

second part involved the synthesis of triphenylmethanol through the reaction between

benzophenone and phenylmagnesium bromide, followed by deprotonation of the resulting

intermediate. Specific values for percent yield and melting point were obtained, indicating

successful completion of the experiment. Overall, the experiment was successful in

demonstrating important concepts of organic chemistry, including reaction mechanisms and

synthesis techniques.
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References Cited

Simão, D., & Cerdeira, A. C. (2016). 4.2. 1.2. Synthesis of Methyl Triphenylmethyl Ether. Comprehensive

Organic Chemistry Experiments for the Laboratory Classroom, 312.

Orgo Chem, I. I. Grignard Synthesis of Triphenylmethanol.