Post Lab #7
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Project #7 The SN2 Reaction Factors Affecting SN2 Reaction
*****
TA: *****
Work Alongside *****
INTRODUCTION
SN2 reaction happens in a single concerted step. The mechanisms involve the
development of a leaving group and the creation of a bond to the nucleophile simultaneously
(Weldegirma, 2021). The nucleophile, an electron-rich species, attacks the backside of electron-
deficient species and inverts the configuration. During the process, the leaving group deflects the
nucleophile from undertaking from the front side. In order for an SN2 to perform, there needs to
be a strong nucleophile; the stronger the nucleophile, the faster the reaction will occur. The more
sterically hindered the electrophile, the more readily it reacts under SN2. A slow reaction rate is
caused by the alkyl groups branching off of beta and alpha carbons, preventing the nucleophile
from attacking the backside of the species. (Kubelka & Bickelhaupt, 2017). Therefore, methyl
substrate is more reactive. Additionally, tertiary groups are favored. SN2 reactions prefer polar
aprotic solvents because polar protic solvents block the true properties of a nucleophile.
(Hamlin, Swart, & Bickelhaupt, 2018).
EXPERIMENTAL SECTION
Add 5mL of the solvent to three test tubes in 1:5:4 ratio; Add 20 drops of triethylamine to test
tube #1, then 20 drops of tripropylamine to test tube #2, then 20 drops of ethyldiisoproylamine
to test tube #3
⇩
Add 10 drops of iodomethane to each test tube; then, discard waste into salt waste jars
⇩
Get 3 new test tubes and add 20 drops of triethylamine to each tube with 15 drops of iodoethane
to test tube #1, 15 drops of 1-bromopropane to test tube #2, and 15 drops of
2-bromopropane to test tube #3; observe the subsequent reaction
⇩
Get the unknown amine and a dry test tube and add 40 drops of the unknown chemical into the
tube
⇩
Add 20 drops of iodomethane slowly; then add 2mL of solvent
⇩
Allow the tube to stand for 10-15 minutes (Cool the tube in ice bath if it gets too hot)
⇩
Use vacuum filtration to get precipitate
⇩
Allow solid to dry and identify the melting point to identify unknown substrate
TABLE OF CHEMICALS
Chemical
Name
Chemical
Structure
Molecular
Formula
Molecular
Weight
Boiling
Point
Melting
Point
Chemical
Appearance
Acetone
C
3
H
6
O
58.08 g/mol
56.2ºC
-95.35ºC
Flammable and
irritant
Diethyl Ether
C
4
H
10
74.12 g/mol
34.6ºC
-116.3ºC
Flammable and
skin/eye irritant
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Pentane
C
5
H
12
72.15 g/mol
36.1ºC
-130ºC
Flammable,
skin/eye
irritant, health
and
environmental
hazards
Triethylamine
(CH
3
CH
2
)
3
N
101.19 g/mol
89ºC
-113.7ºC
Corrosive,
irritant, and
flammable
Tripropylamine
C
9
H
21
N
143.27 g/mol
156ºC
93.5ºC
Flammable,
corrosive, toxic
and skin/eye
irritant
Iodomethane
CH
3
I
141.94 g/mol
42.43ºC
-66.5ºC
Health, toxic,
and skin/eye
irritant
Iodoethane
C
2
H
5
I
155.97 g/mol
72.2ºC
-111ºC
Flammable and
skin/eye irritant
2-Bromopropane
C
3
H
7
Br
122.99 g/mol
60ºC
-89ºC
Flammable,
and health
hazards
Idiisopropylamine
C
8
H
19
N
129.25 g/mol
127ºC
-46ºC
Flammable,
corrosive,
toxic, and
skin/eye irritant
1-Bromopropane
C
3
H
7
Br
122.99 g/mol
71ºC
-110ºC
Flammable,
skin/eye
irritant, and
health hazards
Methyltributylam
monium Iodide
C
13
H
30
IN
327.295
g/mol
N/A
189ºC
Skin/eye
irritant
Trimethylphenyla
mmonium Iodide
(C
6
H
5
)N(CH
3
)
3
I
263.12 g/mol
N/A
187ºC
Corrosive,
toxic, and
skin/eye irritant
Benzyltrimethylam
monium Iodide
(C
6
H
5
)CH
2
(C
H
3
)
3
I
277.14 g/mol
N/A
178ºC
skin/eye irritant
Methyltripropylam
monium Iodide
(CH
3
CH
2
CH
2
)
3
N(CH
3
)
3
I
315.28 g/mol
N/A
20ºC
N/A
RESULTS
Amines
Test Tube
Time of
Precipitation
Formation
Texture
Appearance
#1
10 seconds
Cloudy
White
#2
2 minutes
Cloudy
White
#3
More than 15 minutes
Cloudy
White
Alkyl Halide
Test Tube
Time of
Precipitation
Formation
Texture
Appearance
#1
20 minutes
Cloudy
White
#2
N/A
N/A
N/A
#3
2 minutes
Cloudy
White
Unknown
Melting point
Determined
structure
Identity
Unknown
175ºC
(C
6
H
5
)CH
2
N(CH
3
)
3
Trimethylphenylamm
onium Iodide
DISCUSSION
Based on the results from the experiment, it can be implied that steric hindrance is
present as a rate of an SN2 reaction. Steric The triethylamine
CONCLUSION
Based on the experiment, the theoretical background and results are connected.
REFERENCES
Weldegirma, Solomon. 2021. “Experimental Organic Chemistry: Laboratory manual for CHM
2210L and CHM 2211L.”Lab handbook. University of South Florida. Tampa, Fl. P. 119
Hamlin, T. A., Swart, M., & Bickelhaupt, F. M. 2018. Nucleophilic Substitution (SN 2):
Dependence on Nucleophile, Leaving Group, Central Atom, Substituents, and Solvent.
Chemphyschem : a European journal of chemical physics and physical chemistry
,
19
(11),
1315–1330.
Kubelka, J., & Bickelhaupt, F. M. 2017. Activation Strain Analysis of SN2 Reactions at C, N, O,
and F Centers.
The journal of physical chemistry. A
,
121
(4), 885–891.
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