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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Related Questions
Chemistry
I think I understand most of this except for what mechanisms these resemble. Thanks!
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Question 2
The reaction of sodium ethoxide with iodoethane to form diethyl ether is classified as:
O an electrophilic substitution
O a nucleophilic substitution
O a radical substitution
O an electrophilic addition
A Moving to another question will save this response.
O Type here to search
a.
立
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Br
tBuO
H3C
H3C
CH2
H2
Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are
measured, if the rate of the reaction is found
alkyl halide the reaction is second order. The substitution reaction is thus termed SN2, and the elimination reaction is
be dependent upon the concentration of the nucleophile as well as the
termed E2. These reactions are bimolecular and take place in a single step. In the SN2 reaction, the nucleophile attacks
the a-carbon from the backside and displaces the leaving group with an inversion of configuration occurring at the
carbon. In the E2 elimination reaction, strong base removes an acidic hydrogen from the B-carbon and an alkene is
formed as the leaving group is expelled from the a-carbon. This elimination follows Zaitsev's rule whereby the more
substituted alkene is generally formed. In E2 elimination, both the B-hydrogen and the leaving group must be oriented
anti to each other.
The same reaction…
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Use the dropdown menu to indicate whether the rate of the reaction shown below will increase,
decrease, or remain the same when the reaction conditions are changed to X or to Y or to Z
(see below).
NaCN
Br
CN
CH3CN
X: Change the leaving group from Br to CI
Y: Increase the concentration of haloalkane
Z: Increase the concentration of NaCN
X:
choose your answer...
Y:
choose your answer...
Z:
choose your answer...
>
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Most nucleophilic
3860
Br
CI
F
Least nucleophilic
Answer Bank
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( do 1 2 3 with explanation plz)
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2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but
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of negative charge needed to be a good nucleophile.
CH3CH₂O
CH3CO₂
CH3SO3
H₂O
CH₂OH
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Pls help ASAP
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What is the rate-determining step in the mechanism of an electrophilic substitution reaction of benzene?
Select one:
OA. Attachment of the electrophile to benzene ring.
OB. Bonding of catalyst to electrophile precursor.
O C. Reformation of acid catalyst.
OD. Formation of the electrophile.
OE. Loss of H+ ion form arenium ion intermediate to reform aromatic ring.
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Which set of reactants will form the expected
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???
IOH
"OH
1. Hg(OAc)2, H20, 2. NABH4
Br2 in CCI4
1) МСРВА 2) Нз0*
1) Os04, pyridine 2) NaHSO3, H20
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Consider the molecular models in Figure 12. In which case will a nucleophile
react more readily with the carbonyl group?
Your answer
Figure 12
A
carbonyl group
H :0:
H
H:O:
| ||
HICH
H-C-C-O-C-H
H
||||
H-C-C―CI:
Н
H
B
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Determine the mechanism (SN1, SN2, E1, or E2) and major product for the reactions below. Consider the type of LG (primary, secondary, or tertiary) AND the reactant type (strong nucleophile, weak base, weak/hindered base) to determine the correct mechanism/product!
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Subject- chemistry
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H₂C H
H₁C Br
NBS
CH,
CH₂
CC, hv
**You may assume that Br-Br is formed by a side reaction that occurs (which we discussed in class). This is useful for
one of the steps of the mechanism.
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Do 1,3,4,5
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c)
nucleophi ic
due to Lone pair
f)
Netthev
8) For each molecule below, predict the partial charge on each atom. Then, rank the molecules based
on nucleophilic strength.
Mg-Br
5
LO
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A Grades for Angela Winston: CHEM-2
0 0 C
←
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52
Heavy rain soon
A
Choose the reagent(s) that would be most likely to complete this reaction.
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Question 11 of 27
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1.OsO. (catalytic)
2 NMO
Bra
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1. BH-THE
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1. Hg(OAC), M.O
2. NaBH., NaOH
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enter,
shift
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Please answer this organic chemistry question:
show all three steps and radical mechanism for hydrobromic acid in peroxide reacting with 3-methylene-2-ene. Are there multiple products?
Background information just in case needed for the intial question above ? but if not needed just ignore this background information: which of the following compounds will react the quickest?
A) Fluorine with a tertiary radical
B) chlorine with a tertiary radical
C) Bromine with tertiary radical
D) chlorine with a primary radical
E) bromine with a primary radical
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Which of the following statements about an SN2 reaction is true?
A. There are two transition states.
B. There is one energy maximum.
C. The transition state can be isolated and studied.
D. For a carbon electrophile in the transition state, the hybridization of an sp3
carbon remains unchanged.
E. The reaction rate does not depend on the concentration of the electrophile.
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Circle every active position and indicate at eachwhether it is electrophilic or nucleophilic.
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Review topics]
[References)
1.
CI
NaOH
NH2
NaCI
H20
2.
OH
NAHCO3
12
H20
CO2
Nal
a = Proton transfer
d = Electrophilic addition
g = SN1 Nucleophilic substitution
b = Lewis acid/base
c = Radical chain substitution
e = El Elimination
h = SN2 Nucleophilic substitution
f= E2 Elimination
Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers.
1.
2.
Retry Entire Group
9 more group attempts remaining
nswer
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- Chemistry I think I understand most of this except for what mechanisms these resemble. Thanks!arrow_forwardoutinerlegacyUrl=%252Fwe Your answers are saved automatically. Remaining Time: 2 hours, 35 minutes, 42 seconds. * Question Completion Status: A Moving to another question will save this response. Question 2 The reaction of sodium ethoxide with iodoethane to form diethyl ether is classified as: O an electrophilic substitution O a nucleophilic substitution O a radical substitution O an electrophilic addition A Moving to another question will save this response. O Type here to search a. 立arrow_forwardBr tBuO H3C H3C CH2 H2 Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found alkyl halide the reaction is second order. The substitution reaction is thus termed SN2, and the elimination reaction is be dependent upon the concentration of the nucleophile as well as the termed E2. These reactions are bimolecular and take place in a single step. In the SN2 reaction, the nucleophile attacks the a-carbon from the backside and displaces the leaving group with an inversion of configuration occurring at the carbon. In the E2 elimination reaction, strong base removes an acidic hydrogen from the B-carbon and an alkene is formed as the leaving group is expelled from the a-carbon. This elimination follows Zaitsev's rule whereby the more substituted alkene is generally formed. In E2 elimination, both the B-hydrogen and the leaving group must be oriented anti to each other. The same reaction…arrow_forward
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