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Discovering the identity of an unknown organic

compound requires finding which functional groups it contains and then determining its molecular and three-dimensional structure.

Four basic areas of inquiry are useful for identifying the nature of an unknown compound. 1. Physical Properties of compounds 2. Classification by solubility 3. Elemental analysis 4. Classification test for functional groups
This experiment focuses on the 4th area of inquiry.

The presence of Functional Groups is identified by reacting the compound to a reagent which gives a specific visible result

The Experiment is divided into 4 parts: Test for Unsaturation

Test for Aromaticity Test for Acidity and Basicity Test for Alkylhalides

I. Bromine in Methylene Chloride

Preparation of Acetylene

Mechanism involved in the Reaction of Bromine in Methylene Chloride

Electrophilic Addition - Halogenation

Theoretical Framework of reaction:

Addition reaction of Bromine (Br2), a red liquid, to a

compound containing a double or triple bond produces a colorless dibromide. (A positive test!) rich to initiate the reaction. Therefore, minimal electron withdrawing groups (Deactivators), such as Carboxyl Groups attached to molecule, would hinder the reaction. react with the Bromine reagent.

The double (or triple bond) must be sufficiently electron-

Unsubstituted Aromatic compounds (Benzene) do not Even if the ring has substituted activating groups (donate

electrons to the ring) the reaction would be a substitution and not an addition.


II. Baeyer Test

Mechanism involved in the Baeyer Test

Redox reaction

Theoretical Framework of reaction:

Potassium Permanganate (KMNO4) is an oxidizing agent.
It has a Purple color

Following the oxidation of an unsaturated compound, the Permanganate ion is reduced to Manganese Dioxide (MnO4), a brown precipitate.
The reaction is important because it doesnt work on alkanes (compounds with carbon-carbon single bonds) or aromatic compounds.

Easily oxidized compounds give a positive

test: a) Most aldehydes give a positive test. b) Formic acid and its esters give a positive test. Often, the brown precipitate fails to form and the solution turns reddish-brown. Alcohols with trace impurities give a positive test. Phenols and aryl amines give a positive test.


POSITIVE TEST: The disappearance of the KMnO4's purple color and the appearance of a brown suspension of MnO2 is a positive test.

a chemical property in which a conjugated

ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. It can also be considered a manifestation of cyclic delocalization and of resonance.


Mechanism Involved in Nitration

Electrophilic Aromatic Substitution

Theoretical Framework of reaction

Benzene derivatives in a general sense react in the same way that benzene does,

although there are some interesting differences.

Nitration of toluene generates a mixture of products. The major products are

those with substitution at the ortho and para positions.

In the case of toluene, ortho (and para) attack result in the positive charge

being spread over two secondary carbons and one tertiary carbon atom (the one bearing the CH3 group).
When reaction of toluene occurs at the meta position, then the resonance

forms of the sigma complex put positive charge over 3 secondary carbons - the same as for benzene.
Appearance of the product (Nitration of toluene) : light yellow to darker yellow-

green liquid


Acidity, from the Bronsted-Lowry concept,

is correlated with the ability of an organic compound to be a proton donor.

Acidity of organic compounds is usually

associated with functional groups containing OH alcohols, phenols, and carbonyl compounds

Basicity, from the Lewis Concept of

Acids and Bases, is the ability or availability of a compound to donate its electron pair.
Basicity is commonly associated with

amines since nitrogen has a lone pair that can be shared with Lewis acids.

I. AgNO Test

Mechanism involved in AgNO Test

Theoretical Framework of Reaction

The silver nitrate test is designed to detect strong acids

especially carboxylic acids.

The presence of an acid is detected by the presence of

replaceable H+ atoms and the formation of precipitates. acids and silver nitrate. Silver nitrate reacts with carboxylic acids to form salts of the carboxylic acid. should be added. Silver salts are soluble in the aforesaid acid.

The essence of this test is the reaction between carboxylic

To verify the presence of the silver salt, dilute nitric acid


POSITIVE TEST: Appearance of precipitate and dissolution of the

precipitate in Nitric acid

II. Silver Acetylide Test

Mechanism involved in Silver Acetylide Test

Theoretical Framework of Reaction

These substitution reactions which ethynes undergo

to form compounds with metals are not occur with the alkenes.
These reactions can be used as tests to distinguish

between acetylene and ethylene.

When acetylene is passed through an ammonical

solution of silver nitrate or cuprous chloride, at room temperature, precipitates of silver acetylide (white) or cuprous acetylide (red) are formed.


Alkyl Halides
Alkyl halides is a group of chemical

compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide.

Alcoholic AgNO Test

Mechanism involved in Alcoholic AgNO Test

Theoretical Framework of Reaction

this test can be used to differentiate aromatic halides from aliphatic


The reaction of an alkyl halide with silver nitrate in ethanol will result

in the formation of a white or yellow silver halide precipitate that is insoluble in nitric acid. warming is necessary.

This reaction quite often proceeds slowly, and occasionally slight Different rate if silver halide precipitation would be expected from

halogen in each of these environments, namely, primary<secondary<tertiary.

Alkyl bromides and iodides react more rapidly than chlorides Aryl Halides are unreactive toward the test reagent.