Analyzing the Separation of Volatile Organic Compounds Through Gas Chromatography

I. Introduction:
Gas chromatography is used to separate and test the purity of compounds. These
compounds are organic and volatile. In gas chromatography, the mobile phase will be
represented by helium, a carrier gas. The stationary phase is a liquid with a high boiling
point on silicone or a polymer. The compound that will be purified must be volatile at
high temperatures in order for it to be analyzed through gas chromatography. In order to
analyze compounds, one will look at retention times, which show how fast the compound
elutes the column. The same retention time does not mean two samples are the same
compound. Retention times and separation of compounds are dependent on column
length and temperature and the flow rate of the carrier gas. In this experiment, the ratio of
products produced will be obtained and compared to literature values. These ratios and
literature values examine the nucleophilic strength of reactive ions used in this
experiment. Two nucleophiles will be present in large quantities (1:1 ratio) in this
experiment. The mechanisms (Sn1 and Sn2) these nucleophiles and the other compounds
go through in gas chromatography will show the relative strength of these nucleophiles.
In addition to using gas chromatography in this lab, microscale liquid-liquid extraction,
as well as non-microscale liquid-liquid extraction, will be used.

Balanced Reaction:

Mechanism:
SN2 Reaction

SN1 Reaction
 II. Table of Reagents:

Reagent Structure MW BP MP Density

(g/mol) (℃) (℃) (g/cm3)

Tert-Butanol 74.12 82.2 n/a 0.775

Sulfuric Acid 98.08 337 n/a 1.84

Water 18.02 100 0 0.9982

Ammonium 97.94 n/a 235 n/a

Bromide

Ammonium 53.49 n/a 338 n/a

Chloride

Sodium 84.01 n/a 50 n/a

Bicarbonate

Tert- 137.02 73 n/a 1.22

Butylbromide

Tert- 92.57 51 n/a 0.851

Butylchloride

III. Safety Information

● Sulfuric acid can give off dangerous vapors, so the snorkel must be positioned
correctly and turned on.
● The products produced, alkyl halides, are volatile and toxic so do not inhale or
ingest them.
● Put liquid waste in the correct waste bottles under the fume hood.
● If there are any chemical spills or vapor exposure notify the TA.
● Individual concerns for chemicals:
○ Tert-Butanol
● Flammable
● Causes severe eye irritation that can lead to eye damage
● Dangerous if it is inhaled
● Respiratory irritant
● Severe skin irritant
● Should not be swallowed
○ Sulfuric acid
● Not combustible
● Can cause serious skin burns and eye damage
● Do not inhale or ingest
● Corrosive to metals
○ Water
● Non-flammable
● Does not irritate skin or eyes
● Safe to ingest
○ Ammonium bromide
● Skin and eye irritant
● Can cause severe eye damage
● Do not inhale or swallow
● Respiratory irritant
● Not flammable
○ Ammonium chloride
● Non-combustible
● Dangerous if swallowed or inhaled
● Severe eye irritant
● Skin irritant
○ Sodium Bicarbonate
● Skin and eye irritant
● Dangerous if swallowed or inhaled
● Can cause severe eye damage
● Non-combustible
○ Tert-Butylbromide
● Extremely flammable
● Skin irritant
 ● Can cause eye severe eye irritation that can lead to eye damage
● Respiratory irritant
○ Tert-Butylchloride
● Extremely flammable
● Serious eye and skin irritant
● Do not swallow or inhale
IV. Procedure:
1. Create a sulfuric acid solution by obtaining 7.5mL of concentrated sulfuric acid
and adding it to 10g of ice inside of a 100mL beaker. The ice will melt when two
components are mixed together, because it is an exothermic reaction.
2. Obtain exactly 3.100g of ammonium bromide and 1.690g of ammonium chloride
and put them into a 125mL Erlenmeyer flask.
3. Add boiling chips to the mixture and then slowly add the sulfuric mixture. The
ammonium salts and the aqueous acid need to be heated together until the salts
have dissolved in the solution before the solution reaches its boiling point.
4. Move the hot solution to a 50mL round-bottomed flask using a short-stem funnel.
5. Add a spin vane to the round-bottomed flask.
6. The solution needs to be stirred and cooled down to 30℃. If the solution is cooled
below 30 ℃, then the salts will start to precipitate, making the solution need to be
reheated in order to dissolve the salts again.
7. When the mixture reaches 30℃ without the formation of a precipitate, use a
Pasteur pipet to get 1.0mL of tert-butanol. Put the tip of the pipet completely
under the solution and barely touching the bottom of the flask.
8. Gently put the components of the pipet into the solution. Write down
observations.
9. Use a water-cooled condenser and stir the sample for about 5 minutes.
10. Leave the solution alone for another 5 minutes.
These steps need to be done in less than 10 minutes for accurate results:
11. The condenser needs to be removed, and the lower, aqueous layer needs to be
extracted with a Pasteur pipet.
12. The aqueous layer needs to separate as much as possible from the mixture inside
of the round-bottomed flask and put it in another beaker.
13. Move the liquids into a 5mL conical vial to make it easier to separate.
14. The entirety of the aqueous layer needs to completely removed even if some of
the alkyl halide is removed in the process
15. Get 0.05g of sodium bicarbonate and put it into the halide layer that is found
inside of the conical vial. This will allow any of the left-over acid to neutralize in
the vial causing a small amount of carbon dioxide gas to he emitted.
16. Using a Pasteur pipet, transfer the alkyl halide mixture into a 3mL conical vial.
Make sure to cap it. Not all the alkyl halide layer is needed to run gas
chromatography on the sample.

Microscale Liquid-Liquid Extraction