Zachary McCarty

Submitted November 2, 2011

Harrison Firebausch
Preparation of a Grignard reagent for the synthesis of triphenylmethanol
Data:
Reaction 1:
Mg
0
+
Br
dry ether
Br
Mg
(Forming the Grignard reagent)
Reaction 2:
O
CH
3
O
+
Br
Mg
2
1. dry ether
2. H
2
SO
4
(aq)
O H

Name magnesium bromobenzene methyl
benzoate
triphenylmethanol sulfuric
acid
M. F Mg C
6
H
5
Br C
8
H
8
O
2
C
19
H
16
O H
2
SO
4

M. W 24.31 g/mol 157.01 g/mol 136.15
g/mol
260.33 g/mol 98.08
g/mol
Amount 1.043 g
0.0429 mol
4.4 mL (6.3 g)
0.040 mol
2.50 mL
(2.7 g)
0.020 mol
2.02 g
(0.0078 mol)
3.0 mL
M.P 166-168
0
C

FTIR cm
-1
: 3467, 3059, 3025, 1597, 1490, 1157, 1010, 757, 696
Percent Yield:






()

()

()
()

Discussion:
This synthesis involved the preparation of a Grignard reagent for the immediate reaction
with methyl benzoate to prepare the product, triphenylmethanol. The reaction was expected to
follow the pathway in which a Grignard reagent reduces a carbonyl compound to the
corresponding alcohol (Reaction 2). Not only are organometallic reagents like Grignard
reagents useful for reducing carbonyl compounds, but also have applications to many organic
syntheses and can also serve as catalysts for further reactions. Through this experiment, many
key laboratory techniques were refined including reflux, crystallization, and separation.
The Grignard reagent was prepared initially by reacting elemental magnesium (1.043 g)
in a pre-dried apparatus fit with a drying tube and a separatory funnel which contained
anhydrous diethyl ether mixed with bromobenzene (4.4 mL). The contents of the separatory
funnel were added to the magnesium in two portions and the reaction of magnesium and
bromobenzene was left to reflux for about 15 minutes forming the Grignard reagent. The
solution was cooled and methyl benzoate (2.5 mL) was then added to the Grignard reagent
and the mix was left to reflux for 5 minutes and then slowly poured onto a solution of ice water
and sulfuric acid (3.0 mL). The reaction mixture was placed in a separatory funnel and the
organic layer was separated (the aqueous layer was re-extracted once), washed with sodium
bicarbonate, and dried with sodium sulfate. The dried solution was filtered, hexanes (~ 12 mL)
were added, and the solvent was left to evaporate for 7 days so the crystals of
triphenylmethanol could form.
The crystals obtained from the synthesis were analyzed for purity by measuring the
melting point, the mass (percent yield), and obtaining an IR spectrum. The experimental FTIR
spectrum indicated that the desired product was formed because of the peak at 3467 cm
-1
(O-
H stretch), showing that the carbonyl was reduced by the Grignard reagent and protinated by
the acid. The two peaks at 1157 and 1010 cm
-1
(C-O stretch) also indicate the carbonyl was
reduced to the corresponding alcohol. It is important to note that the observed peak of the O-H
was less intense than the typical peak of an alcohol probably due to an increase in steric
hindrance caused by the three aromatics of the molecule, also decreasing hydrogen bonding.
At 3059 and 3025 cm
-1
(C-H bend arene) appeared from the aromatics which also gave two
peaks at 1490 and 1597 cm
-1
(C=C). Two additional peaks of interest at 757 and 696 cm
-1
(C-H
bend) were seen, which are characteristic of mono-substituted aromatics
1
. In comparison with
the literature IR spectrum
2
of triphenylmethanol, all of the previously mentioned peaks of
interest are present and the O-H stretch is very weak as well. One notable difference in the
literature spectrum
2
is the peak at ~2900, which would be indicating a C-H stretch of an alkane
which was not expected in the product, however when consulting another literature spectrum
3

of triphenylmethanol this peak is not present but rather the C-H stretch arene peaks. The
percent yield of the reaction was calculated to be 39.2%. The loss of product may have been
caused by the mistake made of heating the reaction prematurely while preparing the Grignard
reagent, but the loss may have also occurred when separating, leaving some product in the
aqueous layer, or when adding the sodium bicarbonate to the organic layer too quickly
because some solution did spill onto the lab bench. Water could have also hydrated the
glassware from the air, which would have reacted with the Gringard reagent instead and could
have caused a loss of product. In comparison to the literature melting point (160-163 C)
1
the
experimental melting point (166-168 C) of the product indicate a slight amount of impurity in
the sample, which may have been caused by a small amount of water in the sample. Overall,
the product formed in this experiment was relatively pure based on the experimental melting
point and FTIR spectrum obtained.
References:
1) Ault, A. Techniques and Experiments for Organic Chemistry ; University Science Books:
Sausalito, CA, 1998; pp. 444-451.
2) Sigma-Aldrich FT-IR spectrum for triphenylmethanol. Retrieved on 11/3/11 from
http://www.sigmaaldrich.com/spectra/ftir/FTIR000852.PDF.
3) FT-IR spectrum provided by The University of Alabama. Retrieved on 11/3/11 from
http://www.bama.ua.edu/~blacksto/CH237/spectra/exp4_tritylalcohol_IR.pdf.