Experiment 3: Synthesis of Benzopinacol and Benzopinacolone

A formal lab report is required for this experiment.

This report should by typed (1.5 spacing for text) and taped into your notebook and then turned
in the week of February 14th at the beginning of lab. Here are the sections that need to be
included. For sections that are new or different, specific instructions are included.
Be sure that you get a good portion of this report completed before and during lab. Show what
you have so far to your lab instructor and ask questions before you leave lab.
Title:
Name(s):
Date:
Introduction: (approximately 2-4 paragraphs)
In this experiment, you are conducting a radical reaction and then a pinacol rearrangement.
Provide an explanation of the three mechanistic steps in every radical reaction (initiation,
propagation and termination) and then discuss the acid-catalyzed pinacol rearrangement
mechanism. Look up a recent example of a pinacol rearrangement in the chemical literature and
make a comment in your introduction about how pinacol rearrangements such as the one
recently utilized by Smith and co-workers3, continue to be important reactions because they are
an efficient method to make difficult to access ketones, etc. Say something about the uses of
benzopinacol and benzopinacolone. Be sure to cite your sources for the details you include in
this section.
Purpose:

Reactions:
Synthesis of Benzopinacol

Ph

OH

HO Ph

Ph

Ph

Ph

Ph OH

Benzophenone

2-Propanol

Benzopinacol

Acetone

Note: Ph = phenyl

Synthesis of Benzopinacolone
Ph Ph

Ph OH

CH3CO2H

Ph

Ph

Ph

Ph

HO Ph

Benzopinacol

Benzopinacolone

Physical Properties
Substance

Structure

Molecular
Formula

MW
(g/mol)

MP (C)

Benzophenone
2-Propanol
Acetone

Iodine

N/A

N/A

N/A

N/A

N/A

N/A

N/A

N/A

N/A

Benzopinacolone

Ethanol

Density
(g/mL)

N/A

Benzopinacol

Acetic Acid
(glacial)

BP
(C)

N/A
N/A

Diagrams:

Figure 3.1: Electronic energy levels and possible transitions

Figure 3.2: Conversion of Benzophenone to the Diradical Species

Figure 3.3: Reflux Set-up

Experimental Procedure: This section should be written in the style used by the Journal of
Organic Chemistry. It will assume that readers of your report are familiar with organic reaction
techniques and therefore a certain level of understanding is expected. In the journal article
format, they also include details of the product characterization. In your case, you will have
yields, appearances, melting points and IR data to include.

Since you are synthesizing 2

compounds, you will have two separate procedures. Click on the pdf link on the course website
to a journal article you should use as an example. Look at the Experimental Procedures section
of this article for the examples.
Here is a rough outline of what to include:
Name of compound. State what was put in the reaction flask and include what type of flask was
used. Include grams and mmol or mL as shown in the examples. State the time and temperature
conditions. Include any specific procedural instructions. State how the reaction was treated after
it finished reacting. State how the compound was purified. Provide a description of product
appearance, yield, percent yield.

Give IR data.

You should write IR (neat) key peak

absorbances that you identify on the spectrum cm-1.

Calculations:
Moles of Benzophenone:
grams of Benzophenone x 1/MW of Benzophenone

Moles of 2-Propanol:
mL of 2-propanol x density of 2-propanol x 1/MW of 2-propanol

Acetic acid:
Catalyst (This will not be the limiting reagent).
Limiting Reagent:

Theoretical Yield:
Moles of LR x MW of product (benzopinacol) x 1 mole Benzolpinacol
2 moles Benzophenone

Percent Yield for benzopinacol

Percent Yield =

Actual Yield
Theoretical Yield

x 100%

Moles of Benzopinacol: Based on grams of benzopinacol YOU have for this reaction
grams of Benzopinacol x 1/MW of Benzopinacol

mL of acetic acid (Calculate in lab after you know the yield of Benzopinacol)

You need to use enough acetic acid to make a 0.5 M solution of Benzopinacol in acetic acid.

0.5 M solution of Benzopinacol in acetic acid (0.5 M = 0.5 moles / liter)

Liters of acetic acid

mL of acetic acid =

moles of benzopinacol
0.5M

Liters of acetic acid

XXX moles benzopinacol

??? liters

0.5M

1000 mL
1 liter

??? liters

1000 mL
1 liter

??? mL

moles of acetic acid (Calculate in lab after you know the yield of Benzopinacol):
mL of acetic acid x density of acetic acid x 1/MW of acetic acid
1 mole
??? mL acetic acid

1.049 g/mL

= ??? mmol acetic acid

60.05 g

Iodine:
Catalyst (This will not be the limiting reagent).
Limiting Reagent:
Theoretical Yield:
Moles of LR x MW of product (benzopinacolone)

Percent Yield for benzopinacolone

Percent Yield =

Actual Yield
Theoretical Yield

x 100%

Mechanisms: Provide the arrows for each step.

Benzophenone to benzopinacol:
Step 1: hydrogen abstraction from 2-propanol

Step 2: hydrogen abstraction from 2-propanol radical

Step 3: dimerization (Combine the 2 benzhydrol radicals)

Benzopinacol to benzopinacolone:

Data:
1. Appearances for Benzopinacol and Benzopinacolone
2. Melting points for Benzopinacol and Benzopinacolone
3. Mass of Benzopinacolone
4. Labeled IR spectra provided for Benzopinacol and Benzopinacolone
Conclusion: (approximately 3 paragraphs)

State and discuss yields and melting points for benzopinacol and benzopinacolone. Were
your melting points close to literature values?

Comment on the IR data and use it to justify success of your reactions. Did you observe key
changes that let you know the reactions worked?

Explain how the success of these reactions might be improved in the future.

References: Cite the lab manual, physical property references, sources for the introduction and
conclusion. For journal article references or books, please use ACS format. Here is an example:
ACS Format:
Journal Articles:
Stermitz, Frank R.; Cashman, Kevin K.; Halligan, Kathleen M.; Morel, Cecile; Tegos,
George P.; Lewis, Kim. Polyacylated neohesperidosides From Geranium caespitosum:
bacterial multidrug resistance pump inhibitors.

Bioorganic & Medicinal Chemistry

Letters, 2003, 13(11), 1915-1918.

Books:
Bruice, P. Y. In Organic Chemistry; Folchetti, N., Mullaney, R., Kaveney, D., Eds.; Pearson
prentice Hall: Upper Saddle River, NJ, 2007, 5th Edition, pp 184-188.