Objective:

 The aim of this experiment is to prepare 1- butanol

Introduction:

The most generally uses classes of synthetic organic reactions is nucleophilic substitution. This is a
second order nucleophilic substitution, SN2. As we know that the reaction required a nucleophile, an
electrophile and a leaving group in order to apply the experiment in nucleophile second order
substitution.

Bromide is an excellent nucleophile and the electrophile is a 1˚ alkyl group, but hydroxide is poor leaving
group due to its negative charge and its basicity. To make the OH- become better leaving group react
the alcohol with p-toluene sulfonyl chloride which will convert OH- into sulfonic acid ester to react with
sodium bromide to produce 1-bromobutane. After that react with the alcohol with phosphorus
tribromide (PBr3), which convert the OH- to “P(OH)X2” leaving group and also which produces free
bromide ions which react with electrophile , replacing the new leaving group .Lastly, use a strong acid to
protonate the OH- group in the presence of the bromide ion , which changes the leaving group in the
presence of the bromide ion , which changes the leaving the group from hydroxide to water ,and allows
the bromide to react in the same mixture . In this experiment we are using the third method to prepare
the 1-bromobutane.We will separate and purify the product using simple distillation.

The reaction will carry out with the specific purpose of making new compound which is a synthetic
reaction. In this experiment, sodium bromide and 1-Butanol are dissolved in water . Sulphuric acid is
added cautiously which generates hydrobromic acid, which turn reacts with the alcohol upon heating to
make 1- Bromobutane.
Reagents:

17.0 g of sodium bromide, NaBr

10.0 mL of n-butyl alcohol (1-butanol, MW= 74.1, d=0.81g/ml)

17 mL distilled water

14.0 mL concentrated sulfuric acid

14.0 mL oh 9M H2SO4

14.0 mL NaHCO3

1.0 mL CaCl2

Apparatus:

100mL round bottom flask

25 mL round bottom flask

Pasteur pipets

Ice bath

Boiling stones

Distillation setup

Reflux apparatus and trap

125 mL separatory funnel

125 mL Erlenmeyer flask

Weighing balance
Procedure:

17.0 g of sodium bromide was placed to the 100 mL round bottom flask. 17.0 ml of water was added.
The flask swirled until the sodium bromide dissolve. 1-butanol was added to the mixture. Then 14 mL
concentrated sulfuric acid to the reactants of the flask and swirl gently to mix the mixture after each
addition.

The flask was assembled to a reflux apparatus using the condense tube attached to the flask. A trap is
attached to the top opening of the condenser to trap HBr gas produced during the reaction. The trap
consists of filter funnel connected to the rubber hose which is attached to the top opening of the
condenser. The filter funnel is clammed upside down at the stem so that its mouth just touches the
surface of the water contained in a beaker. A few boiling chips was added to avoid bumping.

The mixture was refluxed for 1 hour. The heat is turned off after the reflux is over and the condensate
in the condenser drains back to the flask. The mixture transferred to the separatory funnel after the
mixture is cooled. Two layers were formed and the lower layer was discarded. 14.0 mL oh 9M H2SO4
was added to the funnel. The lower layer discarded. 14.0 ml of distilled water was added to the funnel
and the funnel was shaken again. Two layers formed and the lower layer was drained to the beaker.
This layer contains 1-bromobutane. The layer was transferred to the empty separatory funnel and 14 mL
sodium bicarbonate was added. The flas was shaken for 1 minute. The lower layer drained into
Erlenmeyer flask. The product was dried by anhydrous calcium chloride. The flask was swirled until the
liquid is clear.

The 1-bromobutane was purified using simple distillation. The liquid was pipette to the round bottom
flask. Boiling chips was added and the distillation was started. The sample was distilled was collected at
temperature 70°. The distillate collected in-pre weighed flask. Mass and volume of the purified product
was measured and recorded.
Data and Result:

Melting point 95˚c

Mass of round bottom flask before 63.4181g

Mass of round bottom flask after 65.1195g

Mass of 1–bromobutane 65.1195g – 63.4181g

Molar mass of 1- bromobutane 136.904 g/mol

Mass sodium bromide 17.0045 g

No of mol 1-butanol 17.0045 g / 136.904 g/mol

theoretical yield 0.1242 mol X 136.904 g/mol

Actual yield 1.7014g

Percentage yield (1.7014g/ 17.0034g) X 100%

In this experiment, the reaction carried out with the specific purpose of making new compound which
is a synthetic reaction which 1- bromobutane is prepared from 1-Butanol. Sodium bromide and 1-
Butanol are dissolved in water. Sulphuric acid is added cautiously which generates hydrobromic acid,
which turn reacts with the alcohol upon heating to make 1- Bromobutane. The third method used to
prepare the 1-bromobutane. The product separated and purified using simple distillation.

CH3CH2CH2CH2-OH2+ + Br- CH3CH2CH2CH2-Br + H2O

The distillate should be collected at temperature 95˚C above because the boiling point of this product
is nearly to 1-Bromobutane which has 101˚C as it boiling point. The distillate is almost not enough to be
collected at temperature 95˚C above. Alcohol does not undergo nucleophilic substitution reactions
because hydroxide ion is strongly basic and poor leaving group. The leaving group is a group of atom
which departs with the electron pair used to bond them with the substrate. Alcohols readily undergo
SN2 because the sulphuric acid was added which protonate the hydroxyl group in the presence of the
bromide ion which chenges the leaving group from hydroxide to water, and allows bromide ions to react
with it in the same mixture.

From the calculation, the percentage yield for this experiment is 10.0058% which is less than 50%. This
is because too much loss of distillate. The product also almost not enough to be collected at
temperature 90˚C to 95˚C. Small amount of gas from the 100 ml round bottom flask was release to
surrounding so we do not get an accurate an actual mass in this experiment.

Conclusion:

The experiment was involving second order nucleophilic substitution, SN2. The 1-Bromobutane was
prepared from 1-Butanol.The theoretical yield for this experiment is 17.0034 g while the actual yield is
1.7014 g. The percentage yield is 10.0058%.The melting point is 95˚C nearly to the boiling point of 1-
Bromobutane which is 101˚C , so the product in this experiment is 1-Bromobutane.

Reference:

1) https://www.linfield.edu/assets/files/chem/Courses/CHEM%20322/Siller%20FA%202016%201-
bromobutane.pdf
2) http://chemistry.csudh.edu/faculty/noel/CHE317L/Preparation%20of%201-bromobutane.htm
3) S. M. Klein, C. Zhang, Y. L. Jiang, Tetrahedron Lett. 2008, 49, 2638–2641. DOI:
10.1016/j.tetlet.2008.02.106. https://chemistry.stackexchange.com/questions/77198/why-do-we-
need-sulfuric-acid-in-creating-alkyl-bromide-and-not-in-creating-alkyl
Questions:

1. Density of salt water is 1027 kg/m3, there contained some of bromobutane or hydroxide ions

2. Alkyl halide change from the top layer to the bottom layer at the point where water is used to
extract the organic layer because the alkyl halide is denser compared to the water.

3. The purpose of this wash is to prevent the formation of polybrominated butanes from addition
any more bromine to the 1-bromobutane. The bicarbonate reacts with the unreacted bromides to
form CO2 and sodium bromide which is inert salt.

4. Anhydrous CaCl2 has high affinity to water , so it will absorbed water surrounding.