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SN2 Reactions Lab Notebook by Ben Zinke, Airyn Laird and

Makesa Brantley were the lab partners,
10/24/2023.

Objectives:
• To produce 1-bromobutane from 1-butanol and NaBr with sulfuric acid as a catalyst.
• Facilitate a Sn2 reaction.
• Use NMR to identify impurities in product formed.

Safety:
Goggles were worn in the lab. All spent chemicals were placed in the appropriate waste containers, and
the hood was kept closed when not in use. Special care was taken when working with concentrated
sulfuric acid such as gloves and working under the vent hood.

Procedure:
• 30 g of NaBr, and 30 mL of water were placed in a 250mL round bottom flask and shaken until
most of the salt was dissolved.
• 22.8mL of 1-butanol were added round bottom flask and then the flask was put in an ice bath.
• The round bottom flask sat in the ice bath for ~5min and then 25mL of concentrated sulfuric acid
was added to the flask under the hood in 5 mL increments.
• After the sulfuric acid was added, the round bottom flask was attached to a reflux arm and set in
a hot water bath to reflux for 30 minutes.
• Once the reflux had run for 30 minutes, the round bottom flask was removed, and top layer was
removed with a pipet into a 50mL Erlenmeyer flask.
• Next, 2.370g of CaCl2 was added to the Erlenmeyer flask to clarify the liquid.
• The liquid was then carefully poured into a clean, 100 mL round bottom flask and attached to a
reflux condenser, Y adapter, condenser arm, and averter into a 100mL beaker to fractionally
distill the liquid in the round bottom flask.
• The sample in the 100 mL round bottom flask distilled for ~20 min. The distillate was then dried
with ~3.5g of sodium sulfate until clumping of the sodium sulfate stopped.
• The dry solution of 1-Bromobutane was then prepared for the NMR and scanned to identify any
impurities.

Data/Observations:

• Mass of NaBr used for reflux: 30.039g

• Volume 1-butanol added in reflux: 22.8mL
• mL of 1-butanol was calculated from 18.5 grams to 22.8 mL by dividing the mass by the density
to get the volume of 1-butanol needed.
• To test if the bottom layer of the round bottom flask was aqueous after the reflux, 2 mL of the
bottom layer was pipetted into a test tube and RO water was added and stirred to see if they
would dissolve. This trial showed that the bottom layer was aqueous as the bottom layer
dissolved readily in the water.
• Mass of CaCl2 used to clarify by the liquid before fractional distillation: 2.370g.
• The sample that was distilled had a brownish color to it from the bromine.
• Temperature at which 1-Bromobutane began to distil: 70 *C.
• Possible continents of round bottom flask before fractional distillation: Bromide, butanol, sulfuric
acid, water, bromobutane.
• The distillate appeared cloudy from water contamination and the solution had water clumped on
the surface of the nonpolar product.
• Amount of sodium sulfate added to the distillate after fractional distillation: ~3.5g.
• Mass of amber jar with lid to store product: 57.475g.
• Mass of amber jar with lid and product: 72.950g.
• Mass of product (~1-bormobutane): 15.475g.