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REACTION KINETICS: THE SOLVOLYSIS OF TERT-BUTYL CHLORIDE
Performed February 10, 2023
Michael McClory
By:
Kian Houman and Adam Nachate
Submitted on February 27, 2023
Theory:
In an SN1 reaction, the crucial step that determines the rate of the reaction is the departure of the
leaving group, which results in the formation of a carbocation intermediate. The stability of the
carbocation intermediate plays an important role in determining the energy required for the transition
state during the formation of the carbocation. The more stable the carbocation, the lower the energy
required for the transition state, and the faster the reaction proceeds. The substrate involved in this
reaction contains the leaving group (Cl
-
), which, upon departure, creates the carbocation that
subsequently binds with the nucleophilic hydroxyl group, as illustrated in Figure 1.
Figure 1: SN
1
reaction mechanism of the solvolysis of tert-butyl chloride
Procedure:
Refer to the Chemistry 202 BLD Lab Manual (1)
Data and Results:
Table 1: Rate constant and rate of reaction depending on concentrations and temperature of reactions.
Part A
70%
H2O/30%
acetone
Part B
70%
H2O/30%
acetone
Part C
80%
H2O/20%
acetone
Part D
70%
H2O/30%
acetone
Part E
70%
H2O/30%
acetone
Temperature (
K)
295.5
295.0
295.0
283.1
303.0
Tert-butyl chloride
concentration (M)
0.030
0.015
0.030
0.030
0.030
Sodium hydroxide
concentration (M)
0.003
0.0015
0.003
0.003
0.003
Average time for 10% of
hydrolysis (s)
32.84
15.98
5.97
77.08
13.27
Rate constant (s
-1
)
0.0030
0.0063
0.0168
0.0013
0.0754
Rate of reaction (Ms
-1
)
0.000090
0.000095
0.000504
0.000039
0.002262
Sample calculation Part A
Initial molarity of tert-butyl chloride in reaction mixture
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Related Questions
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*****
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Note that the bromonium ion can exist as two
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L.
20
Based on the information in the introduction, what is the expected melting point of these
+
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yONng pont, which set of stereoisomers
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CH3
Br-
Br2
.CH3
CH2Cl2
CH3
H3C
H3C
Br
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anhydrous solvent such as CH,Cl,.
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Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CH3
CH3
CH3
CH3
H3C
H3C
:Br:
:Br:
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MgBrl
Cul
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||
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arrangement you like, so long as they aren't touching.
If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area.
A
No Reaction
?
Click anywhere to draw the first
atom of your structure.
Åš
Ć
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In cases where there is more than one answer, just draw one.
Br
CEN
I
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Inorganic product
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[ClO2](M)
[OH-](M)
Initial rate (M/s)
0.060
0.030
0.0248
0.020
0.030
0.00276
0.020
0.090
0.00828
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1.
a: What will happen to the rate of the reaction if [ (CH3) 3CBr]
is doubled
b: What will happen to the rate of the reaction if [H0] is
doubled
c: What will happen to the rate of the reaction if both
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CH3CI / AICI3
•
H3C
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2903
the
at the reaction center of the
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903
182903
SEY
9037
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