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Chm457 Fundamental Organic Chemistryexp 3

1. The document summarizes an organic chemistry experiment to prepare 1-bromobutane from 1-butanol through a nucleophilic substitution reaction. Sodium bromide, 1-butanol, sulfuric acid and other reagents and equipment are listed. 2. The experimental procedure, results, and calculations are described. A 43.57% yield of 1-bromobutane is obtained. 3. In conclusion, the experiment successfully synthesized 1-bromobutane from 1-butanol through an SN2 reaction, as evidenced by the determined product percentage yield.

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Aida Syasya
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114 views7 pages

Chm457 Fundamental Organic Chemistryexp 3

1. The document summarizes an organic chemistry experiment to prepare 1-bromobutane from 1-butanol through a nucleophilic substitution reaction. Sodium bromide, 1-butanol, sulfuric acid and other reagents and equipment are listed. 2. The experimental procedure, results, and calculations are described. A 43.57% yield of 1-bromobutane is obtained. 3. In conclusion, the experiment successfully synthesized 1-bromobutane from 1-butanol through an SN2 reaction, as evidenced by the determined product percentage yield.

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Aida Syasya
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CHM457 FUNDAMENTAL ORGANIC CHEMISTRY

EXPERIMENT 3: Preparation of 1-bromobutane from 1-butanol

Name: Intan Nur Aida Syasya bt Johari (2022864668)


Group : As2531C

Group member’s:

Muhammad Ilyasa’ Bin Hazami 2022830194


Amir Nur Aiman Bin Amir Zahariman 2022475138
Zalila bt Zaharin 2022815076

NAME OF LECTURER: Dr. NAJMAH HASSAN

DATE OF EXPERIMENT:9th NOVEMBER 2022

DATE OF SUBMISSION: 30th NOVEMBER 2022

Allocated mark Mark


Aim/Objection of the
experiment
Introduction
Experimental Procedure
Results and Observations
Calculations
Discussions
Conclusions
Questions
References
TOTAL 30
Objective
1. To produce 1-bromobutane from 1-bromobutanol.
2. Find percentage of yield of 1-bromobutanol.
3. Identify the boiling point of 1-bromobutane.
Introduction
One of the most helpful synthetic organic reactions in this experiment is nucleophilic
substitution. It introduces the second order nucleophilic substitution reaction class. In this
category of reactions, a nucleophile, an electrophile, and a free radical group are necessary.
The nucleophile must be in the favourable range for an electrophile (methyl or 1o) to proceed
uninhibited in order for the substitution mechanism to work, and the leaving group must also
be in the favourable range. This reaction describes the scenario where water acts as the acid's
leaving group. The first two requirements are satisfied since the electrophile is a 1° alkyl
group, the electrophile is the bromide ion, the hydroxide ion acting as a weak leaving group.
CH3CH2CH2CH2-OH + Br----> CH3CH2CH2CH2-Br + H2O
It will be a synthetic reaction where we will conduct a reaction whose primary objective is to
produce a new chemical. It is our responsibility to read the appropriate procedure and
technique before executing this experiment. We need to be comfortable with the process to
be able to go to the lab, set up, and complete the necessary tasks quickly, accurately, and
effortlessly. In this experiment, 1-butanol and sodium bromide are dissolved in water.
Hydrobromic acid is created by the slow addition of sulfuric acid, when heated, this acid
interacts with the alcohol to create 1-bromobutane.
Materials
1. 17.0 g sodium bromide, NaBr
2. 10.0 mL of n-butyl alcohol (1-butanol, MW = 74.1, d = 0.81 g/mL)
3. 17.0 mL distilled water
4. 14.0 mL of concentrated sulfuric acid, H2SO4
5. 14.0 mL of 9M H2SO4
6. 14.0 mL distilled water
7. 14.0 mL saturated aqueous sodium bicarbonate, NaHCO3
8. 1.0 g anhydrous calcium chloride CaCl2

Apparatus
1. 100 mL and 50 mL of round bottom flask
2. Ice bath
3. Boiling stones
4. Condenser Liebig
5. Rubber tube, Beaker
6. 125 mL Separatory funnel
7. Extraction, reflux and distillation setup
8. Analytical balance
9. Heating mantle
10. Erlenmayer flask

Figure 1: extraction setup

Figure 2: reflux setup

Figure 3: distillation setup


Procedure
A) Preparation of n-Butyl Bromide
1. 17.0g of NaBr was placed into a 100 mL round bottom flask and 17 mL of H2O and
10 mL of n-butyl alcohol were added.
2. The mixture then was cooled in an ice bath before 14 mL of conc. H2SO4 was added
with a continues swirling in an ice bath.
3. Several boiling stones were added to the mixture and the reflux setup was assembled
as shown in Figure 2. The mixture was heated to a gentle boil for 60 – 75 minutes.
B) Extraction
1. The heat source was removed and allow the apparatus to cool down before the round
bottom flask was disconnected.
2. The reaction mixture then was poured carefully into 125 mL separatory funnel and
shake well the funnel for several times to obtained 2 layers.
3. Vent the pressure occasionally.The lower layer, aqueous layer from the funnel.
4. 14 mL of 9M H2SO4 was added, and the funnel was shaken well as previous step
(step 2).
5. Allow the layer to separate before discard the lower layer.
6. 14 mL H2O was added into the funnel and shook for few times as previous step
(step 2). Allow the layers to separate.
7. The lower layer, which contains n-Butyl bromide was taken into a small beaker.
Discard the lower layer after confirming the exact layer has been saved.
8. Return the alkyl halide to the funnel and 14 mL of saturated aqueous NaHCO3 was
added little at the time while swirling the funnel.
9. The funnel then was shaking few times and vent the pressure as step previous (step
2).
10. The lower alkyl halide layer was discarded into a dry Erlenmeyer flask. 1.0 g
of anhydrous CaCl was added to dry the solution (drain all water that left inside the
product). The drying process can be accelerated by gently warming the mixture on
a steam bath.
C) Distillation
1. The clear liquid was transferred into a 25 mL round bottom flask.
2. Few boiling stones were added, and crude n-butyl bromide was distilled using
distillation process as Figure 3.
3. The temperature maintains in between 94 ⁰C and 102 ⁰C.
4. The product obtained in receiving flask (50 mL round bottom flask) was weighed.
5. Results and data obtained were calculated and jotted down in the data given in
result section.
Result and Observations
Mass of: (g)
100 mL Round bottom flask 49.0151
100 mL Round bottom flask + Sodium 66.0165
bromide solution
Sodium bromide solution 17.0014
50 mL round bottom flask 45.3686
50 mL round bottom flask + product 51.8945
solution (1 bromobutane)
Product solution (1-bromobutane) 6.5259
n-Butyl alcohol (1butanol)(10 mL) 8.1

1 mL of n-Butyl alcohol =0.81g


Temperature obtained (boiling point product): 68o C
Product characteristic = Slightly Cloudy Solution

Calculation
Percent yield %
From the experiment: 1-butanol: MW= 74.1 gmol-1, p = 0.81gmL-1
1-bromobutane:MW =? gmol-1, p = 1.27gmL-1
Sodium bromide: MW = 102.89 gmol-1
1-bromobutane: MW = 137.02 gmol-1 (actual)
n of 1-butanol= m = 8.1 = 0.1093 mol
MW 74.1
n of NaBr = m = 17.0014 = 0.1652 mol
MW 102.89
Theoretical yield = 0.1093 mol x 137.02 gmol-1 = 14.9763 mol
Percentage yield % = Experimental yield x 100 = 6.5259 x 100 = 43.57%
theoretical yield 14.9763
Discussion
CH3CH2CH2CH2-OH + HBr -> CH3CH2CH2-Br + H2O
The dynamics of SN2 are depicted in the diagram above.At the substrate carbon , the SN2
reaction often takes place in an inverted configuration.With respect to the leaving group , the
nucleophile approaches the substrate carbon from the back side.Water is used as a solvent in
this experiment since it contains a hydrogen atom that is attached to a strongly
electronegative element.Our product has a boiling point of 68oC.Since the hydroxide ion is
highly basic and has a weak leaving group , alcohol does not undergo nucleophilic
substitution reactions.The leaving group is a set of atoms that have lost the electron pair that
binds them to the substrate.Alcohols , on the other hand , easily undergo SN2 , due to the
addition of sulfuric acid, which protonates the hydroxyl group in the presence of the bromide
ion, converting the leaving group from hydroxide to water and allowing bromide ions to react
with it in the same mixture.
Sulfuric acid has two functions: it raises the amount of protonated alcohols in the reaction
mixture and it helps tie up the water molecules produced in the reaction, changing the
equilibrium in favour of the alkyl bromide.The percentage yield for this experiment is
43.57%,according to the calculations .Since 1-butanol and 1-bromobutane are flammable
liquids that may irritate our hands , we must wear gloves when conducting the
experiment.Sulfuric acid is a highly concentrated acid that has the potential to damage our
skin.After handling the chemicals,make sure to wash our hands .

Conclusion
In conclusion, the experiment was successful as 1-bromobutane was synthesised from 1-
butanol and the percentage yield of product was determined. From the results, the theoretical
yield of 1-bromobutane is 14.9763 mol and the experimental yield is 6.5259 mol. The
percentage yield of the experiment calculated is 43.57%.

Questions

Aqueous sodium bicarbonate was used to wash the crude n-butyl bromide. What is the
purpose of this wash?

To neutralize any unreacted bromide that remains in the crude n-butyl bromide.

References
1. Fadzli, F. M. (2019). Preparation of 1-bromobutane. Retrieved November 12, 2021, from
blogspot: http://fareastzareul1994.blogspot.com/2016/03/preparation-of-1-
bromobutane.html
2. BrainRouter LTD. (2021). Answer to Question #169983 in Organic Chemistry for
Resthyl. Retrieved November 12, 2021, https://www.assignmentexpert.com/homework-
answers/chemistry/organic-chemistry/question-169983
3. JRG Beavor. (2001). Preparation of ethyl ethanoate. Retrieved November 12, 2021,
http://www.rod.beavon.org.uk/ethanoic_prep.htm

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