Ilana Silva

Meredythe Olsen
OC 212 Lab
January, 29, 2016
Benzoin
Equation:
O
O

thiamine
2

OH

O
O

HO
OH

1. KOH in alcohol

HNO3

2. H3 O+

Data:
Table 1
Mass,
moles
Benzaldehy
de
Thiamine
Benzoin

Theoretic
al yield

0.850 g, N/A
0.00801
mol
0.312 g, N/A
0.00092
5 mol
N/A
0.849 g

Actual
yield

Percen
t yield
N/A

Percent
atom
econom
y
N/A

M.P./
M.P
Literatur
e
N/A

N/A
N/A

N/A

N/A

N/A

0.347
g

41%

100%

121-127
C/134135 C

Table 2
Benzoin

Mass
0.118 g

Calculations:
For Table 1:
0.850 g Benzaldehyde ( Bz )

Yield
0.090 g

% Yield
76%

1 mol Bz
=0.00801 mol Benzaldehyde
106.121 g

M.P.
129-132 C

1 mol Th
=0.000925 mol Thiamine
337.268 g
1 mol Benzoin( Ben) 212 g Ben
0.00801 g Benzaldehyde ( Bz )

=0.84906 g Benzoin
2 mol Bz
1 mol Ben
212 g
212 g
=
100 =48
106.121+337.268 443.389
For Table 2:
0.090 g
100 =76
0.118 g
Questions:
4. The functional groups of benzoin are: a hydroxy ketone and an
alcohol.
5. Infrared spectroscopy can be used to determine whether the
product was produced because the product is expected to include an
alcohol functional group. This alcohol can be observed at around 3600
to 3200 cm-1. This observation of the stretch on the IR spectrum can
show that the reaction was successful, but NMR can also be used as
more proof to show that benzoin was successfully produced.
6. NMR can be used to show that there is a difference between
the reactants and the product with regards to structure. Some
differences include: aromatic hydrogens and an alcohol functional
group. Benzoin is expected to have peaks at around 7-8 ppm and an
integration number of ten, while the starting material is expected to
have peaks at different ranges due to different types of protons within
the structure.
7. The catalyst used was the thiamine. Its purpose was to lead to
the condensation of benzoin.
8. Nitric acid and sodium hydroxide were the hazardous
chemicals. Nitric acid is highly corrosive and may burn skin and eyes.
Sodium hydroxide is also highly corrosive and may cause burning
sensations, blurred vision, and shock.
9. This was a green experiment because the atom economy was
100%. Also, the amount of toxic waste was reduced by using thiamine
as the catalyst instead of another catalyst.
10. The Principles of Green Chemistry that were followed include:
Atom Economy, Prevention, Less Hazardous Chemical Syntheses,
Catalysts, and Inherently Safer Chemistry for Accident Prevention.
0.312 g Thiamine (Th )