Post-Laboratory Report Sheet NAME: ___________________________

Organic Chemistry – 118 C Lab Day: M T W Th

Experiment II Lab Time: 9:00 am 1:10 pm 4:10 pm 7:10 pm
Locker #: ___________________________
TA: ________________________________

Base Catalyzed Rearrangement of Benzil to Benzilic Acid

Data Collection:
Starting Materials:
benzil: _________ g; __________ mol

potassium hydroxide: _________ g; __________ mol

Limiting Reagent: ______________________

Product:
benzilic acid: ______________ g;

Description of product appearance: Mel$ng point: _______

Data Analysis:
Calculate the Theoretical Yield (show calculation):

Theoretical Yield: __________ mol; ___________ g

Calculate the Percent Yield (show calculation):

Actual Yield: __________ g; ___________ mol Percent Yield: __________%

Comments:
Describe any special conditions, errors or deviations from the stated procedure on the
back of this page. You may attach additional pages if needed.

5
Post-Laboratory Questions
Organic Chemistry – 118 C
Experiment II
NAME: ___________________________
Lab Day: M T W Th
Lab Time: 9:00 am 1:10 pm 4:10 pm 7:10 pm
Locker #: ___________________________
TA: ________________________________

Base Catalyzed Rearrangement of Benzil to Benzilic Acid

1) A side product formed in the benzilic acid rearrangement has been identified as
diphenylmethanol. Suggest a possible mechanism for its formation.

2) Why does benzilic acid only precipitate in acidic solution?

3) Why does the pH need to be <2 to precipitate the benzilic acid? Consider your
answer in terms of pKa’s.

6
4) What factors in the IR indicate the reaction has taken place? The spectra are
provided on pg 25,26 in your lab manual.

5) How does this reaction reflect the Green Synthesis principle of Atom Economy?