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Experiment 7

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Sam Rodriguez
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42 views

Experiment 7

Uploaded by

Sam Rodriguez
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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Name: Date:

Program and section: Score:

EXPERIMENT 6

Characteristic Reactions of Organic Halides

OBJECTIVES

At the end of this experiment, the students should be able to:

differentiate primary, secondary, and tertiary organic halides based on their S, reactivity; and

differentiate S1 and S2 mechanisms.

BACKGROUND INFORMATION

Unlike other organic compounds, most organic halides are synthetic. Organic halides are not flammable.
If the a-carbon is tetragonal or sp³ hybridized, the organic halide can be classified as primary, secondary,
or tertiary depending on the degree of substitution of the a-hydrogen by an R group. Reactivity of these
types of organic halides can be differentiated via a substitution reaction with a nucleophile, depending on
which reactant molecule is involved in the rate- determining step. If the rate of the reaction is dependent
on the organic halide, the reaction is unimolecular (S1); if the rate of reaction is dependent on both the
organic halide and the nucleophile, the reaction is bimolecular (S2).

REAGENTS AND MATERIALS

n-butyl chloride – Ethanolic silver nitrate, 2% Sodium iodide,


AgNO3
tert-butyl chloride 15% (Nal) in anhyd. acetone
Copper wire
sec-butyl chloride Copper oxide (CuO) powder
Matches
Chlorobenzene Alcohol lamp
Test tubes
Calibrated droppers

PROCEDURE

A. Beilstein Test: Copper Halide Test

1. Make a small loop on one end of the copper wire. Heat the loop directly in the oxidizing zone
of a non-luminous flame. Continue heating until the green color disappears.
OPTIONAL: While the loop is hot, dip it in CuO powder and reheat until the oxide adheres to the
loop.

2. Cool the loop slightly and dip it into the sample. Heat the loop with the sample in a non-
luminous flame. 3. A blue to green colored flash in the flame indicates the presence of chlorine.
Name: Date:
Program and section: Score:

B. Sn1 Reactivity: Reaction with Alcoholic AgNO,

1. Place 5 drops of the sample into a test tube.


2. Add 20 drops of 2% ethanolic AgNO3. The reagent must not be turbid when used.
3. Shake the mixture and record the time for a precipitate to form. Describe the color of the
precipitate. If no precipitate has formed after five minutes, heat the test tube in boiling water
and observe for precipitation.

C. S2 Reactivity: Reaction with Nal in Acetone

1. Place 5 drops of the sample into a test tube.


2. Add 2 drops of 15% Nal in anhydrous acetone. The reagent must not be turbid when used.
3. Shake the mixture and record the time for a precipitate to form. Describe the color of the
Precipitate.

Data Sheet

Organic Halide Condensed Beilstein test Result observed/Reaction time


Structural 2% Ethanolic 15% NaI in
formula AgNO3 anhydrous
acetone
n-butyl chloride

Sec-butyl
chloride

Tert-butyl
chloride

Chlorobenzene
Name: Date:
Program and section: Score:

1.) Which organic halide/s studied is/are:


a.) Positive with beilstein test

b.) Most reactive by Sn1 mechanism

c.) Most reactive by Sn2 mechanism

2.) What are the factors that would direct organic halides towards an Sn1 reaction?

3.) What are the factors that would direct organic halides towards an Sn2 reaction?

4.) Why are there organic halides that are unreactive towards Sn1 and Sn2? Explain

Conclusion:

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