Shao 1

Jonathan Shao
TA: Jake Black/Friday
Date: 02/06/2015
EP2-2: Oxidation of Benzoin to Benzil using Nitric Acid
GOALS: 1) to synthesize benzil through oxidation of benzoin using nitric acid 2) to purify the
product using recrystallization and vacuum filtration 3) to test the purity using TLC, MP, and IR
Chemical Reaction Scheme:[1]

Mechanism:[1]

Table of chemical physical and chemical properties[1]*

Chemical
MW
BP/MP
SG OR
structure/formula/name g/mol C
DENSITY
G/ML
(25C)
Nitric Acid[2]
HNO3

63.01

100/NA

1.48

AMT
REQUIRED
/
AMT
PRODUCE
D
4.5 mL

Acetic Acid[3]
C2H4O2

60.05

117118/16.2

1.049

3.0 mL

Hazard/
Precaution

Corrosive/avoid
skin contact

Corrosive/avoid
skin contact

Shao 2

Benzil[4]
C14H10O2

CONTINUED ON PAGE 2
CONTINUED FROM PAGE 1
210.2 NA/94-95 NA
Theoretical:
3
0.59 g

Irritant/avoid
contact

95% ethanol[5]
CH3CH2OH

46.07

78.5/
-114.1

0.789

As needed

Flammable/avoi
d heat, skin
contact

Ethyl acetate[6]
C4H8O2

88.11

77/-83

0.902

~2 mL

Flammable,
toxic/avoid heat,
ingestion

Benzoin[7]
C14H12O2

212.2
6

343/137

1.31

0.60 g

Irritant/avoid
inhalation

Hexane[8]
C6H14

86.18

68/-95

0.66

~2 mL

Flammable/avoi
d heat

Nitric oxide[9]
NO

46.01

21/-11

2.62

---

Toxic/avoid
inhalation and
skin contact.

Nitrogen dioxide[10]
NO2

30.01

-151.7/
-163.6

NA

---

Toxic/avoid
inhalation and
skin contact

*References and notes: all SDS information was obtained from online Sigma Aldrich catalog.
Each substances specifically referenced SDS is included in the references section. Images
obtained through ChemDraw.
Theoretical Yield:
limiting reagent = Benzoin
1 mol of Benzoin reacts to form one mol of Benzil
(0.60 g Benzoin) x (1mol/ 212.26 g) x (210.23 g/mol Benzil) = 0.59426 or 0.59 grams Benzil
Procedure:[1]
1. Heat a water bath to 95C.

Shao 3
2. Add 4.5 mL of concentrated nitric acid and 3.0 mL of acetic acid to 0.6 g of dry benzoin
in a 50 mL Erlenmeyer flask. Add stir bar and clamp to hot water bath. Continue heating
and stirring for 30-40 minutes.
CONTINUED ON PAGE 3
CONTINUED FROM PAGE 2
3. When evolution of red-brown nitrogen oxides has ceased, pour cooled reaction mix into a
beaker with 20 mL ice cold water and stir with glass rod for 1-2 minutes to precipitate the
yellow solid.
4. Collect product via vacuum filtration and rinse product with cold water until no longer
acidic. Recrystallize with hot ethanol and room temperature water. Collect crystals via
vacuum filtration.
5. Run TLC, MP, and IR of product. Divide product with partner.
Clean Up:[1]
Acidic filtrate should be neutralized by transferring to large beaker of water and adding
sodium bicarbonate and pouring down drain with heavy flow of water
All solvents go into the organic waste
References:
1. DiMeglio, C. Course Packet for Organic Chemistry Laboratory, Spring 2015; Yale
University, Department of Chemistry: New Haven, 2015
2. Nitric Acid; Safety Data Sheet No. 7697-37-2; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/sial/258121?lang=en&region=US
(accessed February 5, 2015)
3. Acetic Acid; Safety Data Sheet No. 64-19-7; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/sial/a6283?lang=en&region=US (accessed
February 5, 2015)
4. Benzil; Safety Data Sheet No. 134-81-6; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/aldrich/b5151?lang=en&region=US
(accessed February 5, 2015)
5. Ethanol; Safety Data Sheet No. 64-17-5; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/sial/16368?lang=en&region=US (accessed
February 5, 2015)
6. Ethyl Acetate; Safety Data Sheet No. 141-78-6; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/aldrich/w241407?lang=en&region=US
(accessed February 5, 2015)
7. Benzoin; Safety Data Sheet No. 119-53-9; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/aldrich/b8681?lang=en&region=US
(accessed February 5, 2015)
8. Hexane; Safety Data Sheet No. 110-54-3; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/sial/296090?lang=en&region=US
(accessed February 5, 2015)
9. Nitric Oxide; Safety Data Sheet No. 10102-43-9; Sigma-Aldrich;
http://www.sigmaaldrich.com/catalog/product/aldrich/295566?lang=en&region=US
(accessed February 4, 2015)

Shao 4
10. Nitrogen Dioxide; Safety Data Sheet No. 10102-44-0; Sigma Aldrich;
http://www.sigmaaldrich.com/catalog/product/aldrich/295582?lang=en&region=US
(accessed February 4, 2015)
END EP2-2