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Name: Shamaya Murray

ID No: 28120661
Course: Organic Chemistry
Lecturer: Jason Black
Date: May30, 2016
Title: Identification of functional groups
Aim: Systematically identify the functional groups in the given organic compound and perform
the confirmatory tests after identifying the functional groups.
Abstract:
A functional group is a portion of a molecule that is a recognizable/classified group of bound
atoms. In organic chemistry it is very common to see molecules comprised mainly of a carbon
backbone with functional groups attached to the chain. The aim of the experiment is to
systematically identify the functional groups in the given organic compound and perform the
confirmatory tests after identifying the functional groups. The procedure can be seen as outlined
in the lab manual. It can be concluded that different functional group were identify and
confirmatory test done.

Apparatus/Materials:
Materials
NaOH
Borches reagent
Red litmus paper
NaHCO3
FeCl3
Methanol
Alcohol
Unknown Substance
Schffs reagent
HCL
Sodium Nitrate

Apparatus
Test tube
Ice bath
Water bath
Dropper

Introduction:
A functional group is a portion of a molecule that is a recognizable/classified group of bound
atoms. In organic chemistry it is very common to see molecules comprised mainly of a carbon
backbone with functional groups attached to the chain. The functional group gives the molecule
its properties, regardless of what molecule contains it; they are centres of chemical reactivity.
The functional groups within a molecule need to be identified when naming. The following
functional groups will be discussed in this experiment: Amides, Acids, Phenols,
Aldehydes/ketones, Aldehydes, and Amines.
Ketones/aldehydesa carbon-oxygen double bond, where the carbon is also attached to two
other carbons (ketones) or to a carbon and hydrogen (aldehyde). Ketones and aldehydes react
with a chemical called 2,4-dinitrophenylhydrazine (2,4-DNPH) to form a yellow or orange solid
within a few minutes.

Amides are derived from carboxylic acids. A carboxylic acid contains the -COOH group, and in
an amide the -OH part of that group is replaced by an -NH2 group. So amides contain the
-CONH2 group.
A carboxylic acid is an organic compound that has a carboxyl group. The carboxyl group is a
functional group that contains a carbonoxygen double bond and an OH group also attached to
the same carbon atom, but it has characteristic properties of its own. As with aldehydes and
ketones, carboxylic acid formulas can be written to show the carbon-to-oxygen double bond
explicitly, or the carboxyl group can be written in condensed form on one line. In general,
carboxylic acids are represented by the formula RCOOH, where R is a hydrocarbon group.
An amine is a compound derived from ammonia (NH3); it has one, two, or all three of the
hydrogen atoms of NH3 replaced by an alkyl (or an aryl) group. Like NH3, amines are weak
bases. The functional group of an amine is a nitrogen atom with a lone pair of electrons and with
one, two, or three alkyl or aryl groups attached.
A hydroxyl group is hydrogen bonded to oxygen that is covalently bonded to the rest of the
molecule. Just as with alkenes, alkynes, and ketones, the location of the hydroxyl group is made
by numbering the molecule such that the hydroxyl group has the lowest number possible.
Reagents used in the experiment: Schiffs and Borsches reagent. Schiff's reagent is a chemical
preparation used to test a solution for the presence of aldehydes. It is composed of rosaniline and
sulfurous acid dissolved in water. When the reagent is added to a solution that contains
aldehydes, it turns bright pink in colour. Action of Borsche's Reagent: Aldehydes reacts with 2,4dinitrophenyl hydrazine solution to give a orange/red precipitate of aldehyde 2,4dintrophenylhydrazone derivative.

Methodology:
As outlined in the lab manual.
Results: Table showing different functional groups.
Functional group

Unknown substance +

Observation

Amides

reagents
Unknown substance+ NaOH

Red litmus paper did not


change to blue- absence of

Acids

Unknown substance +

amides
No colour change absence of

Phenols

NaHCO3
Unknown substance +

acid
No violet coloyration- absence

Aldehydes/ketones

Alcohol+FcCl3
Unknown substance +

of phenols
A yellow ppt- prensence of

Aldehydes

methanol+borsches
Unknown substance + schiffs

aldehydes/ketones
Violent colour develop within
2 minutes presence of

Amines

Unknown substance +HCL+

aldehydes
No rapid foaming absence of

Sodium Nitrate

amines

Discussion:
In this experiment because functional groups influence the physical, chemical, and spectral
properties of an organic compound, the identification of a compound's functional groups by
measuring certain physical properties, observing its chemical behavior with different
classification reagents, and studying other spectral data.

What will follow is a series of reaction that happened when each functional group was tested.

Reactions of amides:
Reaction of NaOH:
Amides are decomposed by NaOH to evolve ammonia. The gas can be tested by a moist red
litmus paper which is then turned blue.

Alkaline hydrolysis of aromatic amides to aromatic acid:

The soluble sodium salt of aromatic acid formed from aromatic amides upon hydrolysis is
regenerated as white precipitate in acidic medium.

Biuret Reaction for aliphatic diamide:

When aliphatic diamide is heated at a temperature above its melting point, ammonia is
evolved and crystalline biuret is formed. This biuret in alkaline medium gives a violet
colour with a drop of copper sulphate solution.

Biuret reaction

Hydroxamic acid test for aromatic primary amides:

Hydrogen peroxide reacts with aromatic primary amides to form the hydroxamic acid,
which then reacts with ferric chloride to form ferric hydroxamate complex having a violet
colour.

Reactions of carboxylic acids:

Reaction with NaOH:

Carboxylic acids being acidic dissolves in NaOH to form sodium salt.

Reaction of NaHCO3:

Forms salt with sodium bicarbonate solution with the evolution of carbon dioxide.

Fluorescein Reaction:

The anhydrides of aromatic 1,2-dicarboxylic acids on heating with resorcinol gives a dye
fluorescein. This dye in NaOH solution gives a yellowish red solution with green
fluorescence.

Reactions of phenols:

Reaction of neutral ferric chloride solution:

Phenol form characteristic coloured iron complexes when treated with neutral ferric
chloride solution. E.g. phenol & resorcinol - violet colour, catechol-green etc.

Azo dye formation:

Aryldiazonium salts react with aromatic rings of phenols to form highly coloured azo
compounds. These reactions are called coupling reactions.

Benzoylation:

Phenols react with benzoyl chloride in presence of NaOH, to form esters.

Reactions of primary amines:

Diazotisation:

At low temperature (0-5oC) aromatic primary amines dissolved in strong acids (HCl &
H2SO4) reacts with nitrous acid (NaNO2 +HCl) to form water soluble diazonium salts.
Aliphatic primary amines do not form stable diazonium salts under similar condition. They
react with nitrous acid to yield alcohols and nitrogen (causes rapid foaming).

Azo dye formation for aromatic primary amines:

Aryldiazonium salts react with aromatic rings of phenols to form highly coloured azo
compounds. These reactions are called coupling reactions.

Benzoylation:

Primary aromatic amines react with benzoyl chloride in presence of NaOH, replacing the H
atom attached to the N atom with the benzoyl group to give anilides.

Hinsberg reaction:

Hinsberg reagent is called benzenesulfonyl chloride. Primary aliphatic amines on reaction


with benzenesulfonyl chloride & NaOH gives N-alkylsulphonamide which contains an
acidic hydrogen and hence dissolve in NaOH solution to form the soluble sodium salt. The
solution thus obtained on acidification gives a precipitate of free sulfonamide which is
insoluble in HCl.

Reactions of aldehydes:

Action of Schiffs reagent:

Schiffs reagent is a red solution of rosaniline hydrochloride dissolved in water which is


decolourised

by

passing

sulphur

dioxide.

Dilute solutions of aldehydes when added to Schiffs reagent restores its red colour slowly.

Action of Borsches Reagent:

Aldehydes reacts with 2,4-dinitrophenyl hydrazine solution to give a orange/red precipitate of


aldehyde 2,4-dintrophenylhydrazone derivative.

Reactions of ketones:

Action of Borsches Reagent:

Ketones reacts with 2, 4 dinitrophenyl hydrazine solution to give an orange/red precipitate of


ketone 2,4 dintrophenylhydrazone derivative.

Conclusion:
It can be concluded that different functional group were identify and confirmatory test done.

References:
vlab.amrita.edu,. (2011). Detection of Functional Groups. Retrieved 15 June 2016, from
vlab.amrita.edu/?sub=2&brch=191&sim=345&cnt=1
Solomons, Fryhle. Organic Chemistry, 8th Edition Wiley-India, 2006.
The systematic identification of organic compounds by Ralph L Shriner 8th edition
Frederick George Mann, Bernard Charles Saunders, Practical organic chemistry. 1960