ORGANIC ANALYSIS:

Tests for Functional

Groups
PICS REVIEW CENTER
Solubility Tests
Acid-Base Solubility
◦ 5% NaOH – carboxylic acids and phenols
◦ 5% NaHCO3 - phenols
◦ 5% HCl - amines
Alkenes & Alkynes
Reaction with Bromine Water
◦ Electrophilic Addition
◦ PROCEDURE: Add bromine water in the dark
◦ POSITIVE RESULT: decolorization of orange color
of bromine

Reaction with acidified KMnO4

◦ Oxidative Addition
◦ PROCEDURE: Add KMnO4 with a little sulfuric
acid
◦ POSITIVE RESULT: decolorization of purple
permanganate
Alkenes & Alkynes
Baeyer’s Test for Unsaturation
◦ Electrophilic Addition
◦ PROCEDURE: Add permanganate.
◦ POSITIVE TEST: If more than one
drop of permanganate is needed to
cause a permanent purple color,
then there is unsaturation or an
easily oxidized group. Brown ppt
suspension is found after.
Aromatic Compounds
Ignition Test
◦ Combustion
◦ PROCEDURE: Heat compound in a
flame.
◦ POSITIVE RESULT: Aromatic
compounds often burn with a sooty
yellow flame.
Alkyl Halides
Silver Salt Precipitation
◦ Nucleophilic Substitution
◦ PROCEDURE: Add OH- in warm bath,
neutralize excess base with acid,
then add silver nitrate
◦ POSITIVE RESULT: Formation of silver
halide precipitate: White if AgCl,
cream if AgBr, and yellow if AgI
Alcohols
Chromic Acid Test aka Jones
Oxidation (for primary and
secondary alcohols)
◦ Oxidation
◦ PROCEDURE: Add a few drops of
chromic acid to sample
◦ POSITIVE RESULT: Change of color
from yellow-orange (chromic acid)
to blue-green (chromium 3+)
◦ Note: Also works for aldehydes
Alcohols
Lucas Test (for secondary and tertiary
alcohols)
◦ Nucleophilic Substitution (SN1)
◦ PROCEDURE: Add Lucas reagent to sample
then wait. Lucas reagent is HCl with ZnCl2.
◦ POSITIVE RESULT: Formation of emulsion
(cloudiness). If within 2 to 3 minutes:
tertiary alcohol. If within 5 to 10 minutes:
secondary alcohol. Primary alcohols do not
react.
◦ Note: Only works for water-soluble
alcohols.
Aldehydes
Tollen’s Test
◦ Oxidation
◦ PROCEDURE: Add Tollen’s reagent
(AgNO3 in basic medium)
◦ POSITIVE RESULT: Formation of silver
mirror
Aldehydes
Fehling’s Test (or Benedict’s
Test)
◦ Oxidation
◦ PROCEDURE: Add Fehling’s
reagent to compound. Reagent
is copper (II) ions in basic
medium.
◦ POSITIVE RESULT: Formation of
brick red Cu2O precipitate.
Ketones
Iodoform Test (for methyl
ketones)
◦ Alpha-addition, then nucleophilic
acyl substitution
◦ PROCEDURE: Add I2 and NaOH to
compound
◦ POSITIVE RESULT: Brown color of I2
will disappear and yellow precipitate
(iodoform) will be formed
Aldehydes & Ketones
2,4-DNPH Test
◦ Condensation. 2,4-DNPHydrazone
will form with carbonyl compounds
◦ PROCEDURE: Add 2,4-DNPH reagent
with compound.
◦ POSITIVE RESULT: Formation of a
precipitate
Carboxylic Acids
Sodium Bicarbonate Test
◦ Acid-Base Neutralization
◦ PROCEDURE: Add NaHCO3.
◦ POSITIVE RESULT: Effervescence due
to CO2.
Phenols
Iron (III) Chloride Test
◦ Complexation
◦ PROCEDURE: Add FeCl3 to
compound in suitable solvent
◦ POSITIVE RESULT: Formation of
colored complex (blue, green, or
purple)
Amines
Hinsberg Test
◦ Sulfonamide formation and solubility
◦ PROCEDURE: Step 1 – Add benzenesulfonyl chloride to amine in excess base.
Step 2 – Add acid to test solubility of product.
◦ RESULTS:
◦ Primary amine – clear soln, then precipitate
◦ Secondary amine – precipitate, then no reaction
◦ Tertiary amine – clear soln, then clear soln
Nitro Groups
Iron (II) Hydroxide Test
◦ Reduction (nitro to amine)
◦ PROCEDURE: Add ferrous
ammonium sulfate reagent.
◦ POSITIVE RESULT: Formation of red-
orange Fe(OH)3 precipitate.
Carbohydrates
Molisch Test
◦ Dehydration, then furfural derivative
◦ PROCEDURE: Add Molisch reagent
(alpha-naphthol in ethanol) and
concentrated sulfuric acid
◦ POSITIVE RESULT: Purple interface.
Monosaccharides react faster vs
polysaccharides
Carbohydrates - Ketoses
Seliwanoff’s Test
◦ Dehydration then furfural
◦ PROCEDURE: Add Seliwanoff’s
reagent (resorcinol in HCl) then
heat
◦ POSITIVE RESULT: Formation of
red furfural derivative
Carbohydrates - Pentoses
Bial’s Test
◦ Dehydration, then furfural
◦ PROCEDURE: Add Bial’s reagent
(orcinol, FeCl3, HCl) and then heat
◦ POSITIVE RESULT: Bluish product
Proteins
Biuret Test
◦ Complexation
◦ PROCEDURE: Add Biuret reagent
(Cu2+ in base) to compound
◦ POSITIVE RESULT: Purple solution