Lab Report

Aadib Ahsan
12601946
Lab Session: Monday 9am
Lab Tutor: Steve

Aim
To prepare 1-bromobutane from 1-butanol.
Introduction
In this experiment, 1-bromobutane is produced by the mechanism of Sn2 reactions (otherwise
known as neucleophilic substitution reactions)

Figure 1 shows the basic steps for this experiment.

To prepare 1-bromobutane; a primary alcohol, in this case 1-butanol, is reacted with sodium
bromide solution in an excess of acid (sulfuric acid). As seen in Figure 1, the acid is used to
protonate the hydroxyl group in 1-butanol so as to speed up the reaction. As a result of the
reaction, a bromide ion is formed which then acts as a nucleophile in the following Sn2 reaction.
The final part of the experiment is extracting the pure sample of 1-bromobutane from the
compounds. This is done by distilling it and washing and separating it in a separating funnel.
Finally the product is dried with anhydrous calcium chloride.
Experimental Method
Refer to laboratory manual
During the distillation of the organic layer into the conical flask a large portion of the product was
spilled onto the table by mistake.
Results and Calculations
Mass of 1-butanol used

7.80 grams

Mass of final product

7.02 grams

Refractive index value of final product

Refractive index value in literature

1.436
1.439 (O'Neil, M.J. (ed.). The Merck Index - An
Encyclopedia of Chemicals, Drugs, and Biologicals.
13th Edition, Whitehouse Station, NJ: Merck and
Co., Inc., 2001., p. 263)

IR of our final product

O-H
Stretch
C-O
Stretch

GC Chromoatogram of our product

Molar mass of 1-butanol = 136.904

Molar mass of 1-bromobutane
Mass sodium bromide used = 13 g
No of mol 1-butanol = 7.80 / 136.904
= 0.057 mols
1 mol of 1-butanol need to react with 1 mol Br ion to produce 1 mol 1-bromobutane
0.057 mol of 1-butanol needs to react with 0.057mol Brto produce 0.057mol 1-bromobutane
Theoretical yield = 0.057 x 137.02 = 7.94 g
Actual yield = 7.02 g
Percentage yield = (7.02 g / 7.94 g) x 100%
= 88.41% Yield

Part B Results:
Compound being tested with Silver Nitrate in
Ethanol

Time taken for formation of precipitate

1-chlorobutane

no reaction

2-chlorobutane

16 minutes

2-chloro-2-methylpropane

10 seconds

chlorobenzene

no reaction

benzyl chloride

1 minute

allyl chloride (3-chloropropene)

3 minutes

Compound being tested with Sodium Iodide in

Acetone

Time taken for formation of precipitate

1-bromobutane

13 minutes

2-bromobutane

16 minutes

2-bromo-2-methylpropane

no precipitate (but colour change to yellow)

bromobenzene

no reaction

Discussion
The main issue with our experiment was the fact that we had accidentally spilled half the product
while trying to pour the chemical into a conical flask. This resulted in our percentage yield being
rather low comparatively. Other than this mistake our experiment was a success.
We noticed that the process of trying to differentiate between the organic and aqueous layer in the
separating funnel was more difficult than anticipated due to both the aforementioned substances
being very similarly coloured. Usually a drop of water is added in via a pipette and observed to see

which layer it joins but since the colours were very similar it was hard to observe clearly. One
solution to this problem could be to use dyed water.
For the second part of the experiment, halohydrocarbons were reacted with Silver Nitrate and
Sodium Iodide to determine the speed at which each one reacted. The meaning of the results is
discussed below in the discussion questions.
Going over the results, our IR Spectrometry results seem to be flawed, there was most likely
incorrect usage of the machine during the readings which resulted in faulty results.
Our percentage yield was surprisingly high considering half the liquid product spilled halfway
through the experiment, this could be due to water weight that did not sufficiently dry in the oven.
Discussion Questions:
1) Write mechanisms to show how alkenes and dubiety ether can form as by-products of
the synthesis of 1-bromobutane from 1-butanol

2) What happens to any alkenes and the dibutyl ether formed in the reaction?
They boil off. Butene has a BP of -6.6 degrees and Dibutyl Ether has a BP of 144 degrees.
3) The reaction of 1-butanol with HBr to give 1-bromobutane proceeds by the Sn2
Mechanism. Draw the steps in the mechanism, including a diagram of the transition state.

4) What precipitate forms when your haloalkenes react with

(a) Silver nitrate in ethanol
Silver Halide

(b) sodium iodide in acetone

Sodium Bromide

5) Obtain IR Spectrum of pure 1-butanol and 1-bromobutane, label the absorptions due to
C-O, C-H and O-H bond stretches and the C-H bond bending.
1-bromobutane

C-O
Stretch

C-H
Stretch

1-butanol

O-H
Stretch
C-O
Stretch

C-H
Stretch

6) Compare the IR spectrum of your product with the sample spectra to assess the purity of
the 1-bromobutane you have prepared. In particular, discuss whether or to any 1-butanol is
present; describe how you can tell whether an O-H stretch is due to unreacted 1-butanol or
just to water
The IR Spectrum of our sample and the IR Spectrum of the pure 1-bromobutane seem very
different. However this is most likely due to incorrect usage of the machine when our sample was
being measured. As such it is difficult to tell whether 1-butanol was present or not, but the O-H
stretch is most likely due to water in the air.
7) List 1-chlorobutane, 2-chlorobutane, and 2-chloro-2-methylpropane in decreasing order
of their observed reactivity towards silver nitrate in ethanol. Discuss whether your results
fit an Sn1 mechanism
2-chloro-2-methylpropane > 2-chlorobutane > 1-chlorobutane
Yes, our results fit an Sn1 mechanism as they indicate that the primary halogenoalkane is the least
reactive.
8) List 1-bromobutane, 2-bromorobutane, and 2-bromo-2-methylpropane in decreasing
order of their observed reactivity towards iodide ions in acetone. Discuss whether your
results with an Sn2 mechanism
2-bromo-2-methylpropane < 2-bromorobutane < 1-bromobutane
Yes our results fit an Sn2 mechanism as they indicate that the primary halogenoalkane is the most
reactive.
9) Explain the difference in reactivity you observed between the two primary haloalkenes
1-chlorobutane and allyl-chloride towards silver nitrate in ethanol
1-chlorobutane was much quicker to react, due to the chloride group being further away and as
thus being more susceptible to charges.

References:
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition,
Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 263