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organic chemistry paper
Nucleophilic Substitution Reactions of Alkyl Halides

1. Summary of Experiment
In this experiment we will be comparing the both SN1 and SN2 reactions using various compounds and sodium iodide and silver nitrate. We will be comparing the nature of the leaving group (Cl vs Br) in the 1-halobutanes as well as the effect of the structure of the compound. The effect of the solvent polarity and temperature will also be looked at.
Name
Structure
M.W.
M.P.
B.P.
Density
Toxicity
Sodium Iodide
NaI
149.89 g/mol
661ºC
1304ºC
3.67 g/cm3
Yes
Silver Nitrate
AgNO3
169.87 g/mol
212ºC
444ºC
4.35 g/cm3
Yes
Acetone
C3H6O
58.08 g/mol
-95ºC
56ºC
0.791 g/cm3
Yes
Ethanol
C2H6O
46.07 g/mol
-114ºC
78ºC
0.789 g/cm3
Yes
1-Chlorbutane
C4H9Cl
93.57 g/mol
-123ºC
79ºC
.88 g/cm3
Yes
1-Bromobutane
C4H9Br
137.02 g/mol
-112ºC
101.4ºC
1.26 g/cm3
Yes
2-Chlorobutane
C4H9Cl
93.56 g/mol
-140ºC
68ºC
0.87 g/cm3
Yes
2-Chloro-2-methylpropane
C4H9Cl
92.57 g/mol
-26ºC
51ºC
0.84 g/cm3
Yes
Bromobenzene
C6H5Br
157.01 g/mol
-30.8ºC
156ºC
1.49 g/cm3
Yes
Cis-1-Chloro-2-butene
C4H7Cl
90.55 g/mol
-65ºC
63.5ºC
0.923 g/mL
Yes
Trans-1-Chloro-2-butene
C4H7Cl
90.55 g/mol
-65ºC
68ºC
0.923 g/mL
Yes
1-Chloro-2-methylpropane
C4H9Cl
92.57 g/mol
-131ºC
68ºC
0.883 g/cm3
Yes
2-Bromobutane
C4H9Br
137.02 g/mol
-112ºC
91ºC
1.25 g/mL
Yes
2-Bromo-2methylpropane
C4H9Br
137.02 g/mol
-16.2ºC
71ºC
1.22 g/cm3
Yes

2. Experimental Procedure
1) Label 11 test tubes
2) Place 0.1 mL of the following in a tube
a. 1-Chlorbutane
b. 1-Bromobutane
c. 2-Chlorobutane
d. 2-Chloro-2methylpropane
e. Bromobenzene
f. Mixture of cis/trans 1-Chloro-2-butene
g. 1-Chloro-2-methylpropane
h. 2-Bromobutane
i. 2-Bromo-2methylpropane
3) Next arrange the tubes into the
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