CM133L Organic Chemistry Lab

1st Quarter SY 2019-2020

EXPERIMENT 07: FACTORS AFFECTING THE RELATIVE RATES OF NUCLEOPHILIC SUBSTITUTION REACTIONS

Tubog, Jalil Venice B., Marilyn Miranda

1
Tubog, Jalil Venice B., CM133L/B11, School of Chemical, Biological, Materials Engineering and Sciences, Mapua
University

Substitution reactions, in which one atom or group of atoms replaces another are commonly observed for
organic compounds. Many substitution reactions involve a kind of reacting group called a nucleophile. A
nucleophile contains an unshared pair of electrons that reacts with a site in an organic molecule that has a
deficiency of electrons. Nucleophilic substitution reactions share several characteristics with acid-base
reactions, Groups that are good leaving groups in nucleophilic substitution reactions are weak bases in acid-
base reactions. Strong bases are typically good nucleophiles in substitution reactions. In an acid-base reaction,
a proton is transferred from the conjugate acid of a weak base to a strong base. In a similar fashion,
nucleophilic substitution reactions often involve the transfer of a carbon group from a weak base, the leaving
group, to a stronger base, the nucleophile. Nucleophilic substitution reactions may occur by one of two
common mechanisms, designated SN1 and SN2.
Keywords: Sn1, Sn2 stereocenters

INTRODUCTION
There are two mechanistic models for how an sp2 hybrid orbitals is an empty, unhybridized p
alkyl halide can undergo nucleophilic orbital. In the second step of this two-step
substitution. In the first picture, the reaction reaction, the nucleophile attacks the empty,
takes place in a single step, and bond-forming 'electron hungry' p orbital of the carbocation to
and bond-breaking occur simultaneously. (In all form a new bond and return the carbon to
figures in this section, 'X' indicates a halogen tetrahedral geometry.
substituent This is called an 'SN2' mechanism. In
the term SN2, S stands for 'substitution', the MATERIALS AND METHODS
subscript N stands for 'nucleophilic', and the The reagents used are 1-bromobutane, 2-
number 2 refers to the fact that this is a bromobutane benzle bromide and many more
bimolecular reaction: the overall rate depends so the 1st is the structure of the substrate effect
on a step in which two separate molecules (the get four micro test tubes and each one transfer
nucleophile and the electrophile) collide. A 0.50mL of 15% sodium iodide in acetone in each
potential energy diagram for this reaction of the four micro test tubes add a drop of the
shows the transition state (TS) as the highest test compounds and using a small cork stop
point on the pathway from reactants to each tube and shake it note the formation of
products. A second model for a nucleophilic cloudiness then after that do the steric effect
substitution reaction is called the 'dissociative', which where you will get a to micro test tubes
or 'SN1' mechanism: in this picture, the C-X and each one transfer 0.50mL of 15% sodium
bond breaks first, before the nucleophile iodide in acetone to one test tube and place
approaches This results in the formation of a one drop of bromobutane and one drop of
carbocation: because the central carbon has bromo 2 2 dimethylpropane to the other and
only three bonds, it bears a formal charge of +1. use small cork to stop and shake it then note
Recall that a carbocation should be pictured as the time of cloudiness and observe for 10
sp2 hybridized, with trigonal planar geometry. minutes until the reactions is visible. The after
Perpendicular to the plane formed by the three that do the leaving group effect which to get 2
 CM133L Organic Chemistry Lab
1st Quarter SY 2019-2020
micro test tubes and place one drop of transfer time observe and transfer 0.25 mL of 0.5M
0.50 mL of 15% sodium iodide in acetone toe silver nitrate and repeat the procedures and 9
one test tube place one drop of 1 bromobutane ad 9 record your observations
and one drop of chlorobutane to the other
using a small cork stop each tube and shake it RESULTS AND DISCUSSION
notethe time of formation of cloudiness and
precipitation and record part d is concentration This experiment although has many procedure it really
of nucleophile effect start with two micro test is just a simple experiment involving many reagents but
tubes again and transfer 0.50mmL of 15% has a pattern on every part where the compounds
sodium iodide in acetone to one test tube place bromobutane, 2- bromobutane and benzyl bromide is
one drop of 1.0M 1 bromobutane and one drop involved
of 2 bromobutane to the other using small corks
stop up each tube and shake it observe the Compound Time for OBSERVATION
reaction for about 5 to 10 minutes or until the reaction
reaction is visible and transfer 0.50mL of 1.0M 1-Bromobutane 70s Cloudy
bromobutane to the solution into two micro precipitate
test tubes and transfer 15% sodium iodide in 2-bromobutane No Reaction Light Yellow
acetone in the other and observe the reaction Solution
for 5 to 10 minutes or until the reaction is 2-Bromo- No Reaction Light Yellow
visible and record your observations. For the 2Methylpropane Solution
part 2 its almost simple these are the factors Benzyl Bromide 10s Cloudy
affecting the rate of nucleophilic unimolecular Precipitate
substitution reaction 1st is structure of the
substrate. By getting four micro test tubes and
CONCLUSION
to each one transfer 0.50 mL of 0.1 M silver
solvent extraction and partitioning, is a method to
nitrate in absolute ethanol solution in each of
separate compounds or metal complexes, based on
the four tubes add a drop of the test
their relative solubilities in two different immiscible
coumpounds using small corks stop up each liquids, usually water (polar) and an organic solvent
tube and shake it note the time and formation (non-polar). There is a net transfer of one or more
and observe the reaction for about 5 to 10 species from one liquid into another liquid phase,
minutes or until the reaction is visible and generally from aqueous to organic. The transfer is
record your observations part b on this
driven by chemical potential, i.e. once the transfer is
experiment is the leaving group effect this all
complete, the overall system of chemical components
goes as the last part goes just observe and
that make up the solutes and the solvents are in a more
record your observations. Bat as for the last test
stable configuration (lower free energy). The solvent
the solvent polarity effect which you will
that is enriched in solute(s) is called extract. The feed
transfer 0.5mL of 0.1M silver nitrate in absolute
solution that is depleted in solute(s) is called the
ethanol solution in a micro test tube add one
raffinate. LLE is a basic technique in chemical
drop of tert butyl bromide using small corks laboratories, where it is performed using a variety of
stop up each tube and shake it observe record apparatus, from separatory funnels to countercurrent
and transfer 0.50 mL of 0.1 M silver nitrate in
distribution equipment called as mixer settlers.[not
5% ethanol acetone solution in a micro test verified in body] This type of process is commonly
tube and repeat the observe and record part. performed after a chemical reaction as part of the
The last part on this experiment is the effect of
work-up, often including an acidic work-up.
concentration of the nucleophile and the alkyl
halide the two micro test ubes and to each one
transfer 0.50mL of 0.10M silver nitrate solution
to test using small corks note the time and
observe the reaction and transfer 0.50mL of
0.1M silver nitrate and ethanol and 0.5 mL of
0.1M tert butyl bromide in ethanol. Note the
 CM133L Organic Chemistry Lab
1st Quarter SY 2019-2020
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