Chemical name or Other Given

Names

2-Butanol

2-Butanone

Sodium dichromate

Brief Summary of Hazards

First Aid Measures

Flammable liquid and vapor.

Substance may be harmful is
skin contact is made or if
swallowed. Substance causes
serious eye irritation, and skin
irritation. Substance may cause
drowsiness.

in general consult a
physcian. If in eyes rinse
with water for at least 15
minutes and consult a
physician. Wash affected
area with plenty of water
and soap. If ingested do not
induce vomiting, rinse
mouth and consult a
physician.
in general consult a
physcian. If in eyes rinse
with water for at least 15
minutes and consult a
physician. Wash affected
area with plenty of water
and soap. If ingested do not
induce vomiting, rinse
mouth and consult a
physician.

Substance is extremely
flamable. Substance may be
harmful if inhaled or
swallowed. Substance may
cause drowsiness and causes
severe eye iritation.

Oxidizer; highly toxic by

ingestion. Will cause severe
burns and damage to contact
areas. Fatal if swallowed.

CAUSTIC; WILL CAUSE SEVERE

BURNS AND TISSUE DAMAGE

Proper Handling and

Storage

Exposure and PPE Info

Toxilogical Information

Avoid contact with skin

and eyes, avoid
inhalation of vapors
and dust. Take
measures to nuetralise
electrostatic build up.

wear gloves safety

glasses and a lab coat at
all times. Work with
chemical in fume hood.
Use full face resipirator
as a backup to
engineering controls
when risk assesment
states its appropriate.

Substance can cause

general depressed
behavior, ataxia and coma.
Substance can cause fetal
death. Substance is not
recognised as a human
carcinogen,mutagen or
terotogen.

Avoid contact with skin

and eyes. Avoid
inhalation of vapor or
mist. Use explosion
proof equipment. Take
maesures to prevent
build up of static
charge. Substance is
hygroscopic, store
under inert
atmosphere.
Avoid all contact, will
cause tissue damage.
USE adiquate
ventilation. Keep in dry
well ventilated area

Were gloves, lab coat

and goggles at all time
while handling. Use
respirator as a backup to
engineering controls.

Substance may cause

drosiness or dissiness.
Substance is not seen as a
potential human
carcinogen, terotogen or
mutagen.

Use proper ventilation.

Wear goggles gloves and
a lab coat at all times
while handling.

May cause allergic reaction

if inhaled. Class 1
carcinogen to humans. May
alter genetic information.

Consult a physician, move

out of dangerous area.
Move to fresh air and
administer artificial
breathing if unconscious.
Rinse eyes thouroughly for
15 mins. Do NOT induce
vomiting
DO NOT INGEST; AVOID ALL Avoid all contact. Will
CONTACT. SEEK EMERGENCY cause severe burns.
MEDICAL ATTENTION

Sulphuric acid

Reference

Chemical Name M.W. (g/mol)

Structure

Full body protection and Group 1 carcinogen to

face shield is
humans. Causes severe
recommended. Work
burns.
with adequate
ventilation.

Mp/Bp (C) Density (g/cm^3)

Solubility
in water

Sigma Aldrich

Sodium
dichromate

298

91/NA

2.35

very
soluble

Sigma Aldrich

Sulphuric acid

98.08

3/290

1.84

soluble

Sigma Aldrich

2-Butanol

74.12

-115/98

0.808

soluble

Sigma Aldrich

2-Butanone

72.11

-1.0875

0.805

soluble

Identification of Unknown G:
Unknown G, is a clear liquid, boiling in the range of 99-101oC. The substance smelled
faintly of alcohol, this played a minor role to identification as IR spectra clearly indicated
secondary alcohol peaks. HNMR and C13NMR were performed and these scans were
identified and matched with spectra on the spectral database for organic compounds.
After all these tasks were preformed it was clear that the identity of Unknown G was 2butanol.
The Reaction to Be Preformed:
2-butanol is a secondary alcohol and therefore is not subject to the easy, painful, yield
reducing oxidation which follows the reaction of primary alcohols to aldehydes and then
to carboxylic acids. Since time, requirement of yield and purity are of concern, the Jones
reaction, involving Na2Cr2O7, 3M Sulphuric acid and acetone was used. The Jones
Reaction made sense because of the speed and high yields that typically result.
6g 2-butanol
2/3eq (H2CrO4); 1/3eq of sodium dichromate (8.04g)
70mL 3M Sulphuric acid
15mL acetone
Observations:
Sodium dichromate is an orange crystalline solid. When sodium dichromate was
added to the sulfuric acid solution it was noted that heat was released and a bright
orange solution was obtained. Upon addition of the dichromate solution to the
distillation apparatus it was noted that as soon as the liquid hit the vapor it turned a
dark sludge like brown color and fell down into the flask. While heating it was observed
that a vapor barrier was climbing the column. Eventually after the addition of about
1/3 of the dichromate solution the first drops of the distillation started (slightly below
75oC) and continued to stay within the range of 75-90oC throughout the reaction
process which was collected. As the reaction progressed, the solution seemed to be less
responsive (in terms of scaling temperature) when dichromate solution is added. Heat
was applied via heating mantle to drive the oxidation product (vapor) to the condensing
column, distillation was stopped at 90oC. There was not much water to speak of and
filtering was not required. Product was moved directly to distillation apparatus.

Results:
TLC was performed with 3:1 pet. ether ethyl acetate
Yield:
Mass recovered: 8.71g
7.47mL x 0.806g/mL = 6.02g 2-butanol
6.02g/73.13g/mol =0.0823mol
0.0823mol x 71.11g/mol = 5.85g 2-butanone
%yield = (8.71/5.85)x100=148%
NMR corrected yield: 71.5%

Discussion:

Heat generated from the addition of dichromate to acid solution is caused by an

overall exothermic system process. This process is the deprotonation or reaction of
sulfuric acid with dichromate to form chromic acid. As this reaction is overall exothermic
and we understand that ketones are more reactive than alcohols, the required
activation energy must be overcome to create the final product. This energy comes from
the violent reduction of Cr6+ to Cr3+ and reaction of Na2Cr2O7 with H2SO4.

The overall reaction of 2-butanol to 2-butanone requires a total of 2 electrons to be

donated to be completed. This is believed or supposed to follow the mechanism given
below:

In this mechanism chromium 6 is reduced to chromium 4, it is believed that the lower

oxidation states of chromium also oxidize the reagent. The following reactions are
referenced from: Jerry March, 2007 and were applied to this reaction.
CH3

H3C
OH

CH3

H3C
2

OH
CH3

H3C
2

OH

+
+
+
+

CH3

3 H3C
OH

Cr

6+

+4
Cr

2 Cr

6+

2 Cr+5

+4
Cr

Cr

3+

2 Cr+5

2 Cr

3+

+
+
+
+

CH3

H3C
O

CH3

H3C

OH
CH3

2 H3C
O

CH3

H3C
O

These reactions are thought to occur; and explains that the ratio of 2-butanol to
chromium is 3:2 making 2-butanol the limiting reagent of the experiment. This
formation of Cr (III), Cr (IV) and Cr (V) could also be the reason for a transitional color of
the reaction, being that Cr (VI) is orange and Cr(III) is blue this would make sense with
the creation of a blue/green final color. This change in color is due to d orbital spacing
shifts. As chromium is reduced the orbital spacing lowers to a lesser energy state and
changes the overall extended pi system of the molecule, thus shifting it from the color
orange (absorbing more visible light), to blue/green/black (absorbing little visible light,
mostly shorter wavelengths)

The yield of this reaction was observed to be fairly decent at 8.71g, the initial
large percentage is due to the distillation of acetone in with the fractions collected, this
is accounted for with spectra ratios. The yield of 71.5% is very decent and reasonable,
this is further proof the Jones reagent rarely oxidizes unsaturated bonds and thus the
reason for the reaction is sound. Dichromate is a very powerful oxidizing agent and
tends to chew up hydrocarbons and cause decomposition and production of CO2. The
effective method is centered around the ability to remove 2-butanone before this

happens and often results in small but pure yields; which the purity comes from the
process of distillation itself. Normally distillation would not be required, but the BP of 2butanone is too low (~79OC) to consider rotavaping after an ether extraction.
The final product HNMR contained acetone and 2 butanone, this was not
initially clear as the two large peaks near perfectly overlap. To account for this
combined integration value (and because the peaks of the desired product were right on
with expected proton values) the value of the specific peak (designated at 2.12ppm) was
subtracted to obtain a rough estimate to the ratio of acetone to product. The resulting
values lead to a rough estimate to how much product was actually obtained. To resolve
this issue without the preformed operation a higher resolution NMR could differentiate
the two like peaks. In the product NMR also there is an unidentifiable peak, which could
be some extensive result of the reaction preformed or water (being the only other
molecule involved).