Experimen 5

The Grignard Reaction

TA: Abdel
Partner’s Name:
Name Student: Toan cao
Number : 215230170
Date of Experiment: June 7, 2019
Due Date: June 17,2019

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Introduction 5%

Results 25%

Discussion 40%

Questions 20%

Presentation 10%
 Introduction
The purpose of this experiment is to synthesize diphenylmethanol by using the Grignard
reaction. First of all, The Grignard reaction was synthesized first by the reaction of
bromobenzene with magnesium. Then, let the Grignard reaction in ether solvent would be react
with benzaldehyde.
The Grignard reaction is very important in synthesis of alcohol. Grignard reagents are
strong nucleophiles, and strong bases, so it can attach to carbonyl (C=O) groups. Therefore, it
can be used in the synthesis of carbon-carbon bonds, or rearrangement of C-C.
The reaction includes 3 steps :
 Results

Theoretical Mass of Diphenylmethanol 2.7 g

Percent Yield 35.92 %

Actual Mass of Diphenylmethanol 0.97 g

Theoretical Melting Point of 61- 63 °C

Diphenylmethanol
Table 1: the result table from experiment and observation (Mass of Diphenylmethanol, percent
yield, Mass of Diphenylmethanol, and Melting Point of Diphenylmethanol.
 Discussion

The most important thing for Grignard reaction is that the Grinard reaction should not be
exposed to water because it reacts with water and produce magnesium ions. Therefore, water
oven dry glassware were used in this experiment.
After adding 0.4 g of given dry magnesium to the bottom flask with the mixture of 1.8 ml of
bromobenzene in 9 ml of dry ether, there is a appearance of cloudiness in the solution, then the
color turn to yellow , and grown. It shows the formation of the Grignard reagent. It also generate
a heat at the bottom flask during reaction. When 1.5 mL of benzaldehyde in 4ml dry ether was
add to the formed Grignard reagent through the Claisen adapter, vigorous fizzing was observed.
When 20% HCl was added , two homogeneous layers were observed because all the waste
product were disposed. Ethers layers were at the top, and water were at the bottom, because
Ethers has smaller density than water. Ethers were removed from the mixture by using steam
bath. Ethers has much lower boiling point than diphenyl methanol, so ethers were evaporated.
Then the solution was cooled down in ice bath, diphenyl methanol was crystallized, then the
product was weighted, and determined the boiling points.

The melting points of the crystallize is from 61-63 oC Which is close to the hypothesis
melting points of diphenyl methanol ( 68OC). Therefore, It is an evident to show that the
experiment in lab 5 was done successfully. High yield percent was collected.
Only 33.52 percent of diphenylmethanol was produced. The main reason is that there was
a spilled of reagent from separator funnel during filtration, additional reasons could come from
the evaporation of chemicals through Claisen adapter during adding water and benzaldehyde.
 Conclusion:
The diphenyl methanol was synthesized successfully. The Grinard reagent was made, then mixed
with benzaldehyde to produce diphenylmethanol.
Our hypothesis is diphenyl methanol would be formed through the reaction of Grignard agent
with benzaldehyde.
2Question:
1. A student accidently used methanol as the reaction solvent for this experiment. Once the
bromobenzene and the magnesium were mixed, a vigorous reaction took place and a
volatile liquid was isolated as the main
product. What is the structure of this product and explain briefly how it is formed?
The producs will have a strong nucleophile. The produced Grignard reagent will take proton
from alcohol. The products will be benzene and Mg(OMe)BR.

2. A Grignard reagent was prepared by reacting bromobenzene with magnesium in diethyl

ether. Carbon dioxide gas was then bubbled through the solution, resulting in the
formation of a solid organic product after acidic workup. What is the structure of this solid
product? Draw a mechanism showing how it is formed in this reaction.

3. What was the purpose of adding magnesium sulfate in this reaction?

The purpose of adding magnesium sulfate is to remove the excess water from the ether
layer. The produced water could decrease the percent yield of diphenyl methanol.

4. The following reaction takes place between 2 moles of a Grignard reagent and 1 mol of
ester. Draw a
plausible arrow‐pushing mechanism for this reaction (Hint: consult chapter 10 of your
textbook)