Name:Evalis Arocho

Lab Partner: Sebastian Campos & Iyana Marquez

TA: Cong Pan

12/2/2019

Experiment 12: Grignard Reaction: Synthesis of Triphenylmethanol

Introduction/Background:

In the 1900s and French chemist by the name of Victor Grignard discovered a type of

halides known as organomagnesium halides1. Today, organomagnesium halides are named after

the French chemist Grignard and are known as Grignard reagents1. A Grignard reagent acts as a

strong nucleophile in Grignard reactions and attacks the carbon of a carbonyl group. For

instance, Grignard reagents most commonly react with aldehydes and ketones and create a new

carbon-carbon bond2. Grignard reactions also react with esters in a similar fashion that it reacts

with aldehydes and ketones. However, elimination occurs with esters unlike aldehydes and

ketones. This is because the base expelled in the ester reaction is relatively moderate compared

to the strong bases in aldehyde and ketone reaction2. The most common solvents for Grignard

reactions to occur are in THF or an ether such as the one that is being used in this experiment3. A

substitution reaction occurs in a Grignard reaction and a nucleophilic attack occurs attacking the

electrophilic carbon3.

Figure 1. Detailed Mechanism for the Preparation of Triphenylmethanol from

Phenylmagnesium Bromide:
Figure 2. Four Undesired Side Reactions That Can Occur During the Preparation of

Triphenylmethanol in This Experiment:

Experimental Section:

Part A. Preparation of the Grignard Reagent: Phenylmagnesium Bromide:

Part B. Synthesis of Triphenylmethanol

Table of Chemicals:
Name Bromobenzene Anhydrous diethyl Phenylmagnesium Benzophenone
ether bromide

Chemical
Structure

Formula C6H5Br (C2H5)2O C6H5MgBr C13H10O

Molar Mass 74.12 g/mol 181.31 g/mol 182.22 g/mol
157.01 g/mol

Melting -30.6 °C -116.3 °C - 47.8 °C

Point

Boiling 156.0 °C 34.6 °C - 305.4 °C

Point
IUPAC bromobenzene ethoxyethane magnesium;benzene; diphenylmethano
Name ne
bromide

Physical clear colorless a clear colorless - white solid with

Properties liquid with a liquid with an a flowery odor
pungent odor anesthetic odor

Name Hydrochloric acid Triphenylmethanol Petroleum Ether Anhydrous

Sodium Sulfate
Chemical
Structure

Formula HCl C19H14O C16H14 Na2SO4

Molar Mass 260.3 g/mol 100.2 g/mol 142.04 g/mol
36.46 g/mol

Melting -114.2 °C 164.2 °C -90.6°C 884 °C

Point
Boiling -85.1 °C 380.0 °C 98.5°C 1,429oC
Point
IUPAC chlorane triphenylmethanol heptane disodium;sulfate
Name
Physical colorless watery white crystalline solid clear colorless liquids Clear crystalline
Properties liquid with a sharp, that is insoluble in water with a petroleum-like powder.
irritating odor and petroleum ether odor

*Information Retrieved from PubChem*

Results:

Triphenylmethanol Results
Mass 0.869 g
Appearance clear white powder
Percentage Yield 56.43%

Percentage Yield Calculations:

Percent Yield = (Actual Yield/Theoretical Yield) x100%

Actual Yield of Triphenylmethanol:

0.869 g triphenylmethanol X 1 mol triphenylmethanol = 0.0033384556 mol triphenylmethanol

260.3 g triphenylmethanol
Theoretical Yield of Triphenylmethanol:

01.54 g triphenylmethanol X 1 mol triphenylmethanol = 0.0059162505 mol triphenylmethanol

260.3 g triphenylmethanol
Percentage yield = (0.0033384556 mol) / (0.0059162505 mol) X 100%

= 56.43 %

ercent Recovery =(Actual

Yield/Theoretical
Yield)x100%
Percent Recovery = (3.0
mL/3.5 mL)x100%
Percent Recovery =86%
ercent Recovery =(Actual
Yield/Theoretical
Yield)x100%
Percent Recovery = (3.0
mL/3.5 mL)x100%
Percent Recovery =86%
Discussion:

In this experiment, my lab group obtained a percentage yield of 56.43%. The percentage

yield is quite low, but this could have been caused by a side reaction occurring if water or

moisture managed to get into the mixture. Another cause could be if some of the solution

evaporated. When the melting point was measured for our product sample of triphenylmethanol

we obtained a melting point of 160oC which is 4oC lower than the literature value of 164oC. A

reason as to why the melting point is out of range could be because the melting point that was

taken was for the crude product since we did not purify and recrystallize the triphenylmethanol.

There is a very high possibility that the product is impure. It is important that an aprotic solvent

such as anhydrous diethyl ether because the Grignard reagent is highly basic and will react with

acidic protons; however, diethyl ether does not have acidic protons to react with therefore is the

best solvent to use in this case and aids in the efficiency of the reaction. The overall efficiency of

the reaction is adequate since it is able to proceed by an aprotic solvent without being hindered

however the percentage yield is quite low.

Conclusion:

Overall the experiment was efficient and successful for the most part other than the low

percentage yield of 56.3%. The purpose of the experiment was to generate the Grignard reagent

phenylmagnesium bromide by treating bromobenzene with magnesium metal which was

accomplished in the experiment1. This reaction was carried out in an anhydrous diethyl ether

which correlates with the theoretical background of using an ether solvent to carry out the

Grignard reaction. Once the Grignard reagent of phenyl magnesium bromide was generated it

was reacted with benzeophenone creating a red solution which was then mixed with 0.2 of

diethyl ether. Once mixed and swirled the crude product of triphenylmethanol was formed1.

Thus, the theoretical background and the results match. Because the final product obtained was

crude triphenylmethanol the melting point was lower than the literature melting point of 164oC.

The melting point obtained was 160oC and the percentage yield as stated previously was 56.3%.

This could mean that the product is impure and contains side products which also resulted in a

poor percent yield and melting point but there is also a possibility that some of the solution or

solvent evaporated. Grignard reactions have multiple application in synthesis. Grignard reactions

can react with epoxides to form new carbon-carbon bonds by opening a three membered ring and

forming an alcohol also. It is used by synthetic chemist to transform an alkyl halide or aryl halide

into organomagnesium compound. The purpose of this is for cross-coupling3. Comprehensively,

the experiment accomplished what it set out to do. The Grignard reagent of phenyl magnesium

bromide was generated in order to form triphenylmethanol and the knowledge of Grignard

reagents and reaction were learned.

References:

[1] Weldegirma, S. Experimental Organic Chemistry Lab Manual; University of South

Florida: Tampa, FL, 2018; P. 65- 69

[2] Maiti, S. R., Ashenhurst, J., Byron, Awasthy, A., Himanshu, James, … Aditya Ajay. (2019,

September 11). Reactions of Grignard Reagents. Retrieved from

https://www.masterorganicchemistry.com/2015/12/10/reactions-of-grignard-reagents/.

Accessed December 1, 2019

[3] Libretexts. (2019, June 5). 19.7 Nucleophilic Addition of Grignard Reagents and Hydride

Reagents: Alcohol Formation. Retrieved from

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map:_Organic_Chemistry_(

McMurry)/Chapter_19:_Aldehydes_and_Ketones:_Nucleophilic_Addition_Reactions/19.

07_Nucleophilic_Addition_of_Grignard_Reagents_and_Hydride_Reagents:_Alcohol_Fo

rmation. Accessed December 1, 2019

[4]“PubChem.” National Center for Biotechnology Information. PubChem Compound Database.

U.S. National Library of Medicine. Accessed December 1, 2019.

https://pubchem.ncbi.nlm.nih.gov/.