Reactivity of Alkyl Halides

Matthew Ira L. Tabanao

Chemistry Department, College of Humanities and Sciences,
De La Salle Medical and Health Sciences Institute, City of Dasmariňas, Cavite

11 April 2019

ABSTRACT

Reactions of Alkyl Halides test was performed to determine if the Alkyl halide present in 2-chloro-2-methylpropane,
dichloromethane, and chloroform are primary, secondary, or tertiary. The objectives of this experiment are to understand the
requirements for a first and second order substitution reaction; and predict the products of a substitution and elimination
reaction based on a given condition. Both objectives were successfully done by the students. 2-chloro-2-methylpropane
tested positive in Finkelstein, silver nitrate in ethanol test, and Beilstein test. Dichloromethane tested positive in Finkelstein
and Beistein test. Chloroform did not test positive in any of the test.

Introduction: SN2 response is straightforwardly connected to

To comprehend the reactivity of alkyl halides in
nucleophilic substitution responses (under both SN1 and
SN2 and conceptualize the way that the reactivity relies
upon response conditions and substrate structures. In the
initial segment of this lab we will investigate the reactivity
of alkyl halides in nucleophilic substituitoin responses
through sodium iodide or potassium iodide in CH3)2CO.
We will see that a reagent made out of sodium iodide or
potassium iodide broke up in CH3)2CO is helpful in
grouping alkyl halides as per their reactivity in a SN2
response. The iodide particle is an amazing nucleophile,
while CH3)2CO is a nonpolar dissolvable. The propensity
to shape a hasten builds the fulfillment of the response.
Sodium iodide and potassium iodide are dissolvable in
CH3)2CO however the relating bromides and chlorides are
not solvent. This implies as the chloride and bromide
particles are created, the particles are accelerated from the
arrangement. This drives the harmony of the response to
one side because of Le Chatelier's Principle. In the second
piece of this lab we will perceive how a reagent made out
of silver nitrate broke up in ethanol is helpful in grouping
alkyl halides as indicated by their reactivity in SN1
responses. This procedure is fundamentally the same as the
procedure above as the encourage makes the response be
upgraded. In this response, the nitrate particle is a poor
nucleophile while the ethanol is a decently amazing
ionizing dissolvable. The silver particle, on account of its
capacity to arrange the leaving halide particle to shape a
silver halide accelerate, extraordinarily helps the ionization
of the alkyl halide. This encourage enables the response to
go to fruition.
the centralization of two species, the Nucleophile (Nuc)
and the alkyl halide (RX) experiencing substitution. Both
of these species are associated with the rate-deciding
(accordingly slowest) step. The rate condition would be:
Rate = k[Nuc][RX], where k is a steady dependent on what
species are really included. It is vital to recollect that, thus,
on the off chance that you twofold the centralization of it is
possible that, you twofold the response's rate. In the event
that you cut the fixation down the middle for either, the
rate will likewise be sliced down the middle. The rate of
the response is legitimately connected to the occasions
these two species can crash to respond together. Change
the fixation and you change the quantity of conceivable
crashes.
Unimolecular: Dealing with the rate of the
response. The rate of any SN2 response is legitimately
connected to the fixation just a single animal groups, the
alkyl halide (RX) experiencing substitution. This is the
main species engaged with the rate-deciding (accordingly
slowest) step. The rate condition would be: Rate = k[RX],
where k is a consistent dependent on what species is really
included. It is vital to recollect that, therefore, in the event
that you twofold the convergence of the nucleophile, there
will be NO EFFECT on the rate of the response. Proceed –
include as much as you need – it won't make the response
any quicker! However, cut the grouping of the alkyl halide
into equal parts and the response will back off
considerably – just half the same number of alkyl halides
are experiencing response!
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Objectives:
At the end of this experiment. The students should be
able to:
1. Understand the requirements for a first and
second order substitution reaction; and
2. Predict the products of a substitution and
elimination reaction based on a given condition.
B. Silver Nitrate in Ethanol Test
1. Transfer 1 mL of 1% AgNO3 in ethanol in 4
separate test tubes.
2. Add 2 drops of the following to each test tube: 2-
chloro-2-methylpropane, dichloromethane, and
chloroform.

3. Shake vigorously for 3 minutes.

Methodology:
4. Heat test tubes in a 50°C water bath if no
Reagents:
precipitate has formed and record time when solid
 2-chloro-2-methylpropane start to appear. Stop Heating after 1o minutes.

C. Beilstein Test
 Dichloromethane

 Chloroform
1. Place tip of a copper wire at the hottest region of
the alchohol lamp until flame coloration is
 1% AgNO3 removed.

 15% KI in acetone 2. Cool the wire and dip it in a test tube containing a
few drops of 2-chloro-2-methylpropane.
 Copper wire
3. Place the tip of the copper wire at the flame and
Materials: take note of color of flame produced.

 Test tubes (1.3x10 cm) 4. Repeat the above procedure using

dichloromethane, chloroform, and ethanol.
 Alcohol Lamp
D. Alkyl Bromide Substrate
 Hot plate/stove
1. What observations do you expect when procedure
 Stainless water bath A is repeated using 2-bromo-2methylpropane,
allyl bromide, benzyl bromide, 2-bromobutane,
 Thermometer and 1-bromobutane?

Procedure: 2. What observations do you expect when procedure

A. Potassium Iodide in Acetone (Finkelstein
Reaction)
1. Transfer 1 mL of 15% KI acetone in 4 separate
test tubes.
2. Add 2 drops of the following to each test tube: 2-
chloro-2-methylpropane, dichloromethane, and
chloroform.
3. Shake vigorously for 3 minutes.
4. Heat test tubes in a 50°C water bath if no
precipitate has formed and record time when solid
start to appear. Stop Heating after 1o minutes.
B is repeated using 2-bromo-2methylpropane,
allyl bromide, benzyl bromide, 2-bromobutane,
and 1-bromobutane?
E. Elimination Reaction
1. Draw the structure of the expected product/s of
the following reactions and tell whether the
reaction is E1 or E2.
a. 2-bromo-2-mehthylpropane with sodium ethoxide
b. 2-bromo-2-mehthylpropane with methanol
c. 1-bromobutane and potassium tert-butoxide
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Results and Discussions:

Place all data and observations from the experiment in

this section. Do not forget to include the table titles and
units. For example:

Table 1. Potassium Iodide in Acetone Test

Table 3. Beilstein Test
Substrate Observation
2-chloro-2-methylpropane With precipitate (after 7 Substrate Flame Color
minutes @50°C water bath) 2-chloro-2-methylpropane green color
dichloromethane With precipitate (after 3 dichloromethane green color
minutes shake) chloroform no color
chloroform Without precipitate (after 10 ethanol No color
minutes @50°C water bath)
blank With precipitate (after 9 Table 4. Alkyl Bromide Substrate
mins @50°C water bath
Substrate Expected change Expected Change
with procedure A with Procedure B
2-bromo-2- No precipitate Appearance of
methylpropane white or yellow
precipitate
Allyl bromide Appearance of Appearance of
white precipitate white or yellow
precipitate
Benzyl bromide Appearance of Appearance of
white precipitate white or yellow
precipitate
2-bromobutane Appearance of Appearance of
white precipitate white or yellow
precipitate
1-bromobutane Appearance of No precipitate
white precipitate

Conclusions:
Table 2. Silver Nitrate in Ethanol Test
In conclusion, chemical tests are conducted to
Substrate Observation
determine the functional groups present in a known or an
2-chloro-2-methylpropane With precipitate
dichloromethane Little to no precipitate unknown compound. In some experiments, false positive
chloroform Little to no precipitate or false negative results arises. False positive result are
blank Little to no precipitate compounds which give positive results even though the
functional group is not present, and false negative results
are compounds that contain the functional group but did
not have a result. At the conclusion of this experiment, the
students were able to do all the objectives. 3 compounds
were tested in this experiment: 2-chloro-2-methylpropane,
dichloromethane, and chloroform. 2-chloro-2-
methylpropane tested positive in tests A, B, and C.
Dichloromethane tested positive in tests A and C only.
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Chloroform did not have a positive result in all of the tests.
Chloroform should have a positive result in the Finkelstein
test because it is a primary alkyl halide. The students made
some minor mistakes during the conduction of the
experiment. This mistakes can be lessen by making sure to
handle all reagents and clean all containers.

References:

Reactions of Alkyl Halides. (n.d.). Retrieved from

https://www.scribd.com/document/168096827/Reactions-
of-Alkyl-Halides

Chem 230L Laboratory Report Reactivity of Some Alkyl

Halides. (n.d.). Retrieved from
https://www.scribd.com/doc/228782480/Chem-230L-
Laboratory-Report-Reactivity-of-Some-Alkyl-Halides