Experiment Title

Name ________
Date ___3-7-14_____________
Section _3020-101__________

Equation (structural)

Stoichiometric Data (For any reactants that are part of the balanced equation, base
on the amounts measured in lab)
Compounds
Mole Wt.

Mass or volume

Moles

Reactants (actual)
Acetophenone

120.15 g/mol

2.2 g

* 0.018 moles

Bromobenzene

157.01 g/mol

2.0 mL

*0.02 moles

Product
(theoretical)
1,1
diphenylethanol

198.26 g/mol

Product Data
Mass

Percent Yield
*14%

0.51 grams

* 3.57 g

* 0.018 moles

bp or mp
Lit. 78-82C
Exptl. 77-81C

Spectroscopic Data (add or delete lines as necessary)

wavenumber
identity**
IR

H NMR

13

C NMR

chemical
shift

multiplicity

integration integration
(raw)
(reduced*)

identity
**

1.8

CH3

2.2

OH

7.4

Phenyl
hydrogens

chemical shift
128 & 150
30
77

identity
**
Phenyl
carbons
CH3
The
solvent

Product Structure (correlated to**)

The product formed looks to be 1,1 diphenylethanol
For the C-13, the higher one (150) is the Carbon attached to the other C which has the
OH. The 128 ones are the other carbons in the phenyl rings.

Discussion
The purpose of this experiment was to synthesize an alcohol via a
Grignard reaction. This was acceived using methods for
working with moisture-sensitive reagents. First, 15 mL of
anhydrous ethyl ether was put into a corked test tube. The
funnel was then opening and 5 mL of dry ether was quickly
added. The the Erlenmeyer, I measured out about 2 mL of
bromobenzene and 5 mL of ether. This was then added to the
addition funnel. With water flow initiated, thirty-three percent
of the solution was put into the vessel. The mixture was brought
to a boil. The reaction occurred, and the rest of the
bromobenzene was added along with 2 mL of fresh ether. The
reaction was continued for 25 more minutes. The reaction
slowed and put into warm water to reflux and then cooled in a
cold water bath. The ketone was added into a test tube with 2
mL of ether and added to the funnel. This was added dropwise
and then rinsed with 2 mL of ether. Once at room temp., 10 mL
of sulfuric acid was poured over an ice cube and let to melt.
This was then added to the funnel and added. The liquid in the
flask was tranfered to a separatory funnel and the layers were
seperated. The ether layer was then washed with water. The
ether solution was poured over a hot water solution in the hood.
Once the bubbles had stopped, the water mixture was boiled on
a hot plate and stirred. Then in was cooled with an ice cube and
product formed. The water was then decanted away. Used
heptane, the product was recrystalized and left to air dry. The
mass of the product was .51 grams and had a melting range of
77-81C. The product formed from looking at the NMR data
and the melting range appeared to be pretty pure product of 1,1
diphenylethanol.

Appendix 1
Calculations
1) Show calculation for each starred (*) item in the report.
2) Include a stoichiometric equation if the structural one is not balanced.
18 millimoles of the ketone = .018 moles Ace.
Ace. is the limiting reagent
Bromobenzene is excess
2 mL * 1.5 g/mL = 3.0 g

/ 157.01 g/mol = 0.01911 = 0.02 mol bromobenzene

2.2 g / 120.15 g/mol = 0.018 mol Ace.

0.018 mol x 198.26 g/mol = 3.57 g of product
3.57 g / 198.26 g/mol = 0.018 moles of product
% yield = 0.51 g / 3.57 g x 100 = 14% yield

Appendix 2
References
(Includes sources for physical constants and hazard information.)
Alfa Aesar - A Johnson Matthey Company. Alfa Aesar, n.d. Web. 07 Mar. 2014.