Grignard Synthesis of Triphenylmethanol from Benzophenone

Grignard Synthesis of Triphenylmethanol from Benzophenone

Purpose: The purpose of this experiment was to synthesize the tertiary alcohol triphenylmethanol from a Grignard reagent, phenyl magnesium bromide. The Grignard reagent was synthesized from bromobenzene and magnesium and then reacted with benzophenone to produce triphenylmethanol. It was important that water be excluded from the reaction, in order to prevent the formation of benzene. The reaction of phenyl magnesium bromide and benzophenone was quenched with sulfuric acid, and an extraction was performed in order to separate the organic phase containing the triphenylmethanol from the aqueous phase. The triphenlmethanol was then isolated and purified by crystallization and vacuum filtration.

Reaction Scheme:

Mechanism: The nucleophilic phenyl magnesium bromide attacks the electrophilic carbonyl of benzophenone to form a magnesium alkoxide. This is followed by hydrolysis by an acid to produce the alcohol, triphenylmethanol.

Procedure: The procedure followed was as is described in "Laboratory Manual for Organic Chemistry 2311," Fifth Edition, Jane E. Wissinger, Thomas Custom Publishing, Mason, Ohio, 2006. pp. 34-37. Modifications of the procedure included adding an additional 1.25 mL of bromobenzene to flask containing the magnesium before the start of the Grignard reaction, because of a broken stopcock which let all of the original 2.25 mL of bromobenzene into the flask initially. Then, this additional bromobenzene was slowly added to the flask dropwise in an attempt to start the reaction. However, because the reaction did not begin, the entire procedure up until this point was repeated, this time with an intact stopcock and just the 2.25 mL of bromobenzene as specified in the lab manual. A crystal of iodine was added in order to start the reaction. During the crystallization, as the solution was boiling and after four or five full pipets of petroleum ether were added, no cloudiness was observed. Therefore, instead of adding more drops of petroleum ether, the solution was taken off the hot plate and allowed to cool.

Reagent/Product Table (bold= measured, italics = calculated):

Bromobenzene, C6H5Br

Magnesium,

Mg

Benzophenone, (C6H5)2CO

10% H2SO4

Triphenylmethanol. (C6H5)3COH

1Mol Wt.

157 g/mol

24.3 g/mol

182.21 g/mol

98.08g/mol

260.3 g/mol

Grams

x

0.460 g

3.68 g

X

1.023 g

Moles

0.0214 mol

0.0198 mol

0.0190 mol

0.939 mol

0.00390 mol

mL

2.25 mL

x

x

50.1 mL

x

1Density

g/mL

1.49 g/mL

1.74 g/cm3

1.11 g/cm3

1.84 g/cm3

1.99 g/cm3

1bpt/mpt, ◦ C

130 ◦C /-31◦C

1090◦C /650 ◦C

305 ◦C /47-51 ◦C

337 ◦C /10 ◦C

360 ◦C /164-165◦C

1Solubility in water

insoluble

Insoluble

insoluble

soluble

insoluble

1Hazards

Irritant, environmental hazard

flammable

flammable

Corrosive, toxic

Eye and skin irritant

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Results/Observations:

Data for Triphenylmethanol

Theoretical Yield

Actual Yield

% Yield

Mpt range

Appearance

4.86 grams

1.023 grams

21 %

162.7-164.4 ◦C

Solid white, tiny crystals, no noticeable odor

Calculations:

Limiting reagent:

2.25 mL C6H5Br x (1.49 g C6H5Br/1