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Experiment 11
Experiment 11
1.1
Learning Outcome
The order for the hydrolysis of t-Butyl Chloride is determined.
EXPERIMENT 11 HYDROLYSIS OF T-
Understand the effect on the rate constant while varying the ratio of
water and acetone.
1.2 Theory
(CH)CCl + HO (CH)COH + HCl
Hydrolysis is a type of reaction that breaks down a compound with the help of water
molecules. Since t-Butyl Chloride is a tertiary halogenoalkane, it undergoes
hydrolysis via a SN1 mechanism, which is shown below:
STEP ONE:
Slow
Fast
STEP TWO:
OVERALL:
Since the addition of the alkali is small with respect to the large volume of
water, the system can be assumed as a pseudo first-order reaction. A
pseudo first-order reaction is actually a second-order reaction, but with the
ratio of the both reactants to differ greatly. Hence, the rate of reaction for
t-butyl chloride decreases as the concentration of acetone increases. The
function of the acetone is to react immediately with the carbocation to
stabilize it.
Since the reaction is a first-order reaction, the rate equation can be written
as:
EXPERIMENT 11 HYDROLYSIS OF T-
is
1.3 Relevance
Reactions kinetics is the use of mathematical rate expressions in the
understanding of chemical processes to ensure that a suitable reactor
design and rating for a chemical plant. The knowledge for reaction kinetics
is crucial to allow the concentration of reactants and products to be
calculated at a given time. There are many factors affecting the rate, such
as temperature, pressure and concentration of substrate. In some
reactions such as the production of ammonia, high temperature increases
the rate of reaction. However, the yield decreases due to a forward
exothermic reaction. Hence, a suitable temperature is chosen to ensure
the rate of production to be the most efficient.
2.1 System Used
Water, Acetone, t-Butyl Chloride, Phenolphthalein, Sodium Hydroxide
2.2 Equipment and Procedure
EXPERIMENT 11 HYDROLYSIS OF T-
White Tile
Stopper
Stopwatch
00:00
Burette
Retort Stand
0.01 M NaOH
Conical Flask
t-Butyl C
Refer to page 39-40 in the Laboratory Handbook for the procedure of this
experiment. The experiment is set up as shown in the diagrams below and
is not drawn to scale.
EXPERIMENT 11 HYDROLYSIS OF T-
2.3 Hazards
Rinse Hands with water if there is any spillage or came in direct contact
with any chemicals, as t-Butyl Chloride and Sodium Hydroxide are
corrosive.
Shake the conical flask at an open space region to prevent from
knocking into anyone or any apparatus nearby.
Burettes and Pipettes should be handle with care as they are fragile and
may break easily.
Safety Goggles and lab coats should be worn at all times to increase
protection from any unforeseen circumstances occurring while
conducting the experiment.
2.4 Results
(a) Observed Data
EXPERIMENT 11 HYDROLYSIS OF T-
% Water
% Acetone
Initial Volume (ml)
Final Temperature (
)
27.0
27.5
Table 2: Table for Volume of NaOH added and Time Taken for the
Hydrolysis of t-Butyl Chloride
Volume of
NaOH added,
V0.1 ml
0.0
2.0
3.5
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
Time, t1 min:s
Experiment
1
00:00
00:43
02:15
03:40
04:30
05:30
06:37
08:06
09:43
12:08
16:24
-
Experiment
2
00:00
01:04
02:38
04:06
05:00
05:50
07:09
08:42
10:15
12:05
15:13
21:50
-
Experiment
3
00:00
02:35
06:52
09:55
11:20
13:17
15:05
17:39
20:23
24:29
29:50
36:20
-
Volume of
NaOH added,
(V0.1) dm3
0.0000
0.0020
0.0035
0.0045
0.0050
Time, (t1) s
Experiment 1
0
43
135
220
270
Experiment 2 Experiment 3
0
64
158
246
300
0
155
412
595
680
EXPERIMENT 11 HYDROLYSIS OF T-
0.0055
0.0060
0.0065
0.0070
0.0075
0.0080
0.0085
0.0090
330
397
486
583
728
984
-
Number of
moles of
NaOH
Reacted,
(nNaOH) mol
0.000000
0.000020
0.000035
0.000045
0.000050
0.000055
0.000060
0.000065
0.000070
0.000075
0.000080
0.000085
0.000090
Number of
moles of
(CH3)3CCl
Reacted, (
n(C H ) CCl )
mol
0.000000
0.000020
0.000035
0.000045
0.000050
0.000055
0.000060
0.000065
0.000070
0.000075
0.000080
0.000085
0.000090
3 3
33
ln
ln
0
43
135
220
270
330
[ ( C H 3 )3 CCl ]t
[ ( C H 3 )3 CCl]0
0.000
-0.302
-0.586
-0.821
-0.959
-1.116
797
905
1059
1223
1469
1790
2180
-
[ ( C H 3 )3 CCl ]t
Number of
moles of
Unreacted
(CH3)3CCl,
(n( C H ) CCl )t
mol
0.0000863
0.0000663
0.0000513
0.0000413
0.0000363
0.0000313
0.0000263
0.0000213
0.0000163
0.0000113
0.0000063
0.0000013
0.0000000
Time,
(t1) s
350
429
522
615
725
913
1310
-
Total
Volume of
Mixture in
Conical
Flask,
(VTotal) dm3
0.0510
0.0530
0.0545
0.0555
0.0560
0.0565
0.0570
0.0575
0.0580
0.0585
0.0590
0.0595
0.0600
[ ( C H 3 ) 3 CCl]t
[( C H 3 )3 CCl]0
Concentratio
n of
Unreacted
(CH3)3CCl,
[ ( C H 3 )3 CCl ]t
mol dm-3
0.00169
0.00125
0.00094
0.00074
0.00065
0.00055
0.00046
0.00037
0.00028
0.00019
0.00011
0.00002
0.00000
for Experiment 1
397
486
583
728
984
EXPERIMENT 11 HYDROLYSIS OF T-
-1.299
-1.519
-1.795
-2.169
-2.761
800
1000 1200
ln{[RCl]t/[RCl]0} -1.500
-2.000
-2.500
-3.000
Time, (t1) s
ln
ln
Time, t1
s
0
64
158
246
300
350
429
522
615
725
913
1310
ln
[( C H 3 )3 CCl ]t
[ ( C H 3 )3 CCl]0
0.000
-0.302
-0.586
-0.821
-0.959
-1.116
-1.299
-1.519
-1.795
-2.169
-2.761
-4.341
[ ( C H 3 ) 3 CCl]t
[ ( C H 3 )3 CCl]0
[ ( C H 3 ) 3 CCl]t
[( C H 3 )3 CCl]0
for Experiment 1
for Experiment 2
EXPERIMENT 11 HYDROLYSIS OF T-
= - 0x400
+ 0 600 800 1000 1200 1400
0 f(x)200
R = 0.99
-2.000
ln{[RCl]t/[RCl]0}
-3.000
-4.000
-5.000
Time, (t1) s
ln
ln
Time, t1
s
0
155
412
595
680
797
905
1059
1223
1469
1790
2180
ln
[ ( C H 3 )3 CCl ]t
[ ( C H 3 )3 CCl]0
0.000
-0.302
-0.586
-0.821
-0.959
-1.116
-1.299
-1.519
-1.795
-2.169
-2.761
-4.341
[ ( C H 3 ) 3 CCl]t
[( C H 3 )3 CCl]0
[ ( C H 3 ) 3 CCl]t
[( C H 3 )3 CCl]0
for Experiment 2
for Experiment 3
EXPERIMENT 11 HYDROLYSIS OF T-
f(x) = - 0x
500+ 0.21
R = 0.95
1000
1500
2000
2500
Time, (t1) s
ln
[ ( C H 3 ) 3 CCl]t
[( C H 3 )3 CCl]0
for Experiment 3
500
1000
1500
2000
2500
Experiment 1
Linear (Experiment 1)
Experiment 2
Linear (Experiment 2)
Experiment 3
Linear (Experiment 3)
Time, (t1) s
Figure 4: Comparison of Graphs for Experiment 1, 2 & 3
3.0 Calculations
EXPERIMENT 11 HYDROLYSIS OF T-
Volume of NaOH, V
1
3
=0.0020 dm
1000
Time Taken, t
t=0 min 43 s=43 s
V =2 ml=2
3 3
negligible.
791
g cm3 1 cm3=0.791 g
1000
Mass of t-Butyl Chloride, m R
m A=
mR =0.791
(n( C H
CCl )t =
3 )3
mR 0.00799
=
=0.00008 63 mol
MR
92.57
(n( C H ) CCl )t
) CCl )t =(n( C H ) CCl )0 n( C H ) CCl =0.00008630.000020=0.0000663
(n( C H
1
=0.00799 g
99
m A : mR =99 :1
33
33
33
33
V Total =0.05+0.01+0.02=0.053 dm
[( C H 3 )3 CCl ]t=
( n(C H ) CCl )t
33
V Total
[( C H 3 )3 CCl ]t
0.0000663
=0.00125 mol dm3
0.053
[ ( C H 3 ) 3 CCl]t
0.00125
=ln
=0.302
0.00169
[( C H 3 )3 CCl] 0
Rate Constant for Experiment 1, k 1
k 1=gradient=(0.0027 ) =0.0027 s1
ln
4.0 Discussion
1.For first order rate constants,
[ k ]=
[ Rate]
mol dm3 s1 1
=
=s
[Concentration]
mol dm3
second
rate
constants,
3 1
[ k ]=
[Rate ]
mol dm s
=
=mol1 dm3 s1
2
3 2
[Concentration]
( mol dm )
=k [ A ]
dt
A
3.
d
Rate=
d [ A]
=k d t
[A]
A
ln [ A ] tln [ A]0=kt
ln [ A ] t=kt + ln [ A ]0
4.
ln
{ }
[ A ]t
=kt
[ A ]0
y=mx
The graph of
ln
{[[ ]] }
At
A0
obtained. The rate constant can be calculated with the expression as shown below:
k=gradient =m
5.The slope of a semi-logarithmic plot is obtained by calculating the
instantaneous gradient at that particular point. This can be done by
determining the gradient of two points on the curve that are tightly
spaced together.
The gradient for the graph of Experiment 2 is the steepest, follow by
Experiment 1 and Experiment 3. This result may be due to errors arises
while conducting the experiment. There will always be a delay when
adding the NaOH into the conical flask and would contribute to the sources
of errors in this experiment. Human errors such as parallax errors while
taking measurements are also one of the sources of errors. As only few
EXPERIMENT 11 HYDROLYSIS OF T-
Description
Units
Volume
m3
Density
kg m-3
Molarity
mol dm-3
Mass
kg
Time
Rate Constant
s-1
Molar Mass
g mol-1
MR
7.0 Reference