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I.

Introduction
Reactions in which alkyl halides may be detected are:
a. Beilstein test
The Belsein test is a qualitative test for halides which was developed by Frederich
Konrad. It is conducted by cleaning a copper wire and heating it using the Bunsen burner to form
copper (II) oxide. It is then dipped in the sample to be tested and heated again to the flame. A
positive test is indicated by a green flame caused by the formation of copper halide.
The reactions involved in the said test are:
Cu (s) + O2 - CuO (s)
Adding the organic halide to the wire initiates the reaction below upon heating:
CuO + 2 R-X CuX2 + 2 R-O-X
The volatile CuX2 reacts with the flame to produce another flame that is bluish-green or
green in color.
b. Alcoholic Silver Nitrate Test
The test depends on the rapid and quantitative reaction of alcoholic silver nitrate with
halide ion to produce insoluble silver halide (except fluoride). Silver and other heavy metals
catalyze SN1 reactions of alkyl halides by complexation with the lone-pair electrons of the
halide, making the leaving group a metal halide rather than a halide ion.
Any structural factors which stabilize the electron defficient carbonium ion will
accelerate the reaction. We thus find the expected order of reactivity: Benzyl allyl > 3 > 2 >1
> methyl > vinyl aryl.

II.

Objective
To be able to detect the presence and reactions of alkyl halides and determine the
mechanism of the reaction that they undergo by the use of the methods in the experiment.

III.

Materials and Reagents


Materials
Beilstein Test

Apparatus

Copper wire
Beaker
Bunsen burner
Reaction wih Alcoholic Silver Nitrate

Specification
120mm
50ml

Quantity(pcs)
5
1

Test tube
Test tube rack
Beaker
Iron stand
Iron ring
Dropper
Measuring pipet
Wire gauze
Test tube holder
Volumetric flask
Watch glass
Bunsen burner

Reagents
Water
Ethanol
Silver nitrate
n-butyl alcohol
2-propanol
Tert-butyl alcohol
Copper oxide

IV.

150 ml

3
1
1

5 ml

1
1

50ml
1
1

1
70mm

Amount

From experiment 2
From experiment 2
From experiment 2
Small amount

Procedures
Beilstein Test
1. Make a small loop on a piece of wire 120 mm in length
2. Heat the loop until no green color is detected. While hot, dip in some copper oxide
powder and reheat until the oxide adheres into the loop.
3. Place a small amount of sample to be tested on the copper oxide and heat in the nonluminous flame of a burner-first in the inner zone, then in the outer zone near the lower
edge. Observe the color of the flame produced. Tabulate your results
Tabular data:
samples
n-butyl chloride
2-chloropropane
Tert-butyl chloride

Remarks on Beilstein test

Reaction with Alcoholic Silver Nitrate


1. To 1 ml of alcoholic silver nitrate, add 1-2 drops of alkyl halide. If no precipitate appears
after 5 minutes with occasional shaking, heat in boiling water bath.
2. Note the condition and time interval at which an appreciable amount of the precipitate
appears.
Tabular data:
samples

Time taken for precipitate

to form
n-butyl chloride
2-chloropropane
Tert-butyl chloride

V.

Results and Discussions


A. Beilstein Test
Table 1. Beilstein test for three sample of chloroalkanes
samples
n-butyl chloride
2-chloropropane
Tert-butyl chloride

Remarks on Beilstein test


Green flame appeared
Green flame appeared
Green flame appeared

Beilstein test is a test for the presence of a halide in a compound. This process is done by
heating a copper wire to produce copper oxide and then dipping the hot copper oxide metal to the
sample. If the copper oxide is heated again and it produced a green flame, a positive result can be
inferred or there is a presence of a halide in the compound. (the reaction is given in the
introduction page).

Figure 1. Beilstein test result for the samples


As seen in the figure a green flame is produced when the wire coated with a sample is
heated in an open flame. This result can be accounted for the presence of a halide which was
theoretically possible since all samples did contain a chlorine atom.
Thus, by the experiment performed, the Beilstein test is a reliable test for determining the
presence of a halogen atom in a compound.
B. Alcoholic Silver Nitrate Test
The Alcoholic Silver Nitrate experiment is a test for the reactivity of haloalkanes with
silver nitrate. The mechanism for these reactions is the SN1 mechanism since the samples are
haloalkanes in the presence of a weak nucleophile in a polar protic solvent. These conditions are
higly favorable for an SN1 reaction. The reaction is RX + AgNO3 ---------------> AgX + RONO2

The rate of reaction for organic substances based on substrate conditions is: tertiary
substrate>secondary substrate>>primary substrate. Since tertiary substrates(and also secondary
substrates) produce stable carbocations for the mechanism of an SN1, we would expect the rate
of reaction(which is proportional to the rate of precipitation) to be: tert-butyl chloride>2chloropropane>>n-butanechloride.
But the results that follow doesnt proceed by these expectations as shown by the table.
Table 2. Record of the time taken to precipitate the samples by silver nitrate
samples

Time taken for precipitate

n-butyl chloride
2-chloropropane
Tert-butyl chloride

to form
1s
1s
1s

Figure 2. Precipitate formed from the reaction


The three samples did precipitate by a very small amount of time. This is wrong since nbutylchloride and 2-chloropropane shouldve taken a while to produce the precipitates. One
highly possible reason for this is the presence of chloride ions from the excess hydrochloric acid
in solution when the samples were synthesized by the Lucas test. The chloride ions from the
excess hydrochloric acid reacted with the silver nitrate to produce silver chloride instead of the
chloride ions present in the samples by the process of SN1 mechanism. This proved to offer a
great deal of errors in the judgement of the rate of reaction of the three samples of haloalkanes.
Theoretically speaking, n-butylchloride shouldnt have produced a precipitate in the first
place because it is a primary substrate and would not react by a SN1 mechanism. An E1 reaction
is possible if it is exposed to heat in the presence of a weak base and a polar protic
solvent(ethanol). 2-chloropropane and tert-butyl chloride shouldve precipitated since they are
secondary and tertiary substrates,respectively.
In conclusion, if we want to test the reactivities of the samples by the alcoholic silver
nitrate test, it is highly reccomendable to use the samples already available and not manually
synthesized because other excess reactive reagents will be present if the latter is used.

VI.

Questions
1. What color appears in the procedure A3? What does this indicate?

A green colored flame appeared from procedure A3. This indicates the presence of a
halide ion in a sample.
2. How does the increasing the temperature affect the reaction of alkyl halides?
Increasing the temperature of the reaction of alkyl halides will proceed with an
elimination reaction rather than a nucleophilic substitution. This is highly favorable for
elimination reactions and thus processes that wouldve taken the path of a substitution reaction
will now proceed via elimination. But it doesnt necessarily mean the products from substitution
will never be formed;it only means that the major product formed is from an elimination
reaction.
3. What is the precipitate formed in the reaction of the alkyl halide with the alcoholic silver nitrate?
Show the mechanisms of the reactions involved.
Silver chloride is the only precipitate that will be formed by the SN1 reaction of the
samples and silver nitrate.
General reaction is: RX + AgNO3 ---------------> AgX + ROCH2CH3
The reactions are:
a. For n-chlorobutane : C4H9Cl+AgNO3-C4H9OCH2CH3+AgX(s)+HNO3
b. For 2-chloropropane : C3H7Cl+AgNO3-C3H7OCH2CH3+AgX(s)+HNO3
c. For tert-butyl chloride: C4H9Cl+AgNO3-C4H9OCH2CH3+AgX(s)+HNO3
VII.

Conclusions

Bicol University
College of Engineering
Legazpi City,Albay

Reaction of alkyl halides


(LABORATORY PLAN No. 3)

Submitted to:

Engr. Marco Angelo Dejucos

Submitted by:
Group 7:
Earl Fred Orozco
Francia Rico
Audrey Therese Perez
Samantha Reonal
Adrian Navarra
Group 8:
Kenneth Sta. Ana
Aidan Kyle P. Sanglay
Ferdinand Samar
Maryan Joyce Severo
Mark Vargas