Test 1.

Reaction with bromine

Reagents/Apparatus Br2 in methylene chloride

Visible Results Decolorization of bromine

Summary of Tests Formula of the compound responsible for the visible result TESTS FOR UNSATURATION

Significance of the test Differentiates alkenes from aromatic and aliphatic compounds Shows the presence of = bonds (+) test: decolorization of bromine (-) test: no change in the color of bromine Differentiates unsaturated from saturated and aromatic compounds Shows the presence of unsaturation (+) test: decolorization of KMnO4 (-) test: no change in the color of the solution Differentiates unsaturated and aromatic compounds from saturated aliphatic compounds Shows the presence of unsaturation and aromaticity (+) test: yellow flame with soot (-) test: blue/yellow flame without soot Differentiates aromatic compounds from aliphatic compounds (+) test: yellow solution and evolution of odor (-) test: No change in the color of the solution, no evolution of odor Differentiates aromatic compounds from aliphatic compounds (+) test: formation of a cherry red solution (-) test: no change in the color of the solution Differentiates acidic form basic and neutral compounds (+) test for acid: pH < 7 (+) test for base: pH > 7

2. Baeyer Test

1% KMnO4

Decolorization of KMnO4 from purple into lighter color

MnO4- MnO2 (violet) (brown) 2KMnO4 + H2O 2KOH + 2MnO2 + 3(O)

3. Ignition Test

Bunsen Flame

Formation of a yellow flame and soot

Compound + O2 C (soot) + CO2

1. Nitration

Concentrated HNO3 Concentrated H2SO4

Formation of yellow solution and aromatic odor

TESTS FOR AROMATICITY ArH + (HNO3/H2SO4) ArNO2

2. Le Rosens Test

Formaldehyde in H2SO4

Change into a cherry red/ pink solution

CH3 RCHO H2SO4 Colorless

Par quinone (cherry red)

1. pH of the solution

pH paper

Depending on the color of the pH paper and matching it with the color in

TESTS FOR ACIDITY AND BASICITY H3O+ and OH-

2. NaHCO3 Test

5% NaHCO3 solution

the chart Dissolves strong acids but not weak acids and all bases Precipitate formation Gray precipitate

NaHCO3 + C6H5COOH Na+C6H5COO- + H2CO3

3. AgNO3 Test 4. Silver Acetylhalide Test

2% ethanolic AgNO3 solution Ammoniacal AgNO3 solution

RCHO-Ag

C2Ag + 2NH4NO3 + 2H2O

(+) test for neutral: pH = 7 Differentiates strong acids from weak acids (+) test: dissolution of strong acid (-) test: no dissolution taking place Differentiates acids from bases (+) test: formation of a precipitate (-) test: no precipitate formation Differentiates acids from bases (+) test: formation of a metal acetylhalide (acidic) (-) test: no precipitate formation Shows the presence of alkyl halides (+) test: either blue, blue-green or green flame (-) test: absence of the (+) flame color Shows the presence of alkyl halide in a compound (+) test: precipitate formation with AgNO3 (-) test: absence of precipitate/ no precipitate formed Differentiates alcohols with intermediate molecular weight from alcohols with large molecular weights (+) test: evolution of bubbles (-) test: no evolution of bubbles NOTE: The rate of bubble formation Differentiates primary from secondary from tertiary alcohols (+) tests for different degrees 1o alcohol no reaction o 2 alcohol cloudy solution (3-5 minutes) 3o alcohol, allyl and benzyl alcohol formation of layers (separate phases)

1. Beilstein Test

Copper Wire

2. Alcoholic AgNO3 Test

2% ethanolic AgNO3

Blue flame presence of I2 Blue-green flame presence of Br2 Green flame presence of Cl2 Precipitate formation with different colors AgI - yellow AgBr pale yellow AgCl - white Evolution of gas/bubbles

TEST FOR ALKYL HALIDES RX + CuO(s) CuX2 (source of flame) CuI2 CuBr2 CuCl2 RX + AgNO3 AgX + R+ + NO3AgI AgBr AgCl TEST FOR ALCOHOLS 2ROH + 2Na 2RONa + H2 2R2NH + 2Na 2R2NNa + H2 2RSH + 2Na 2RSNa + H2

1. Na+ Test

Na metal

2. Lucas Test

ZnCl2 in HCl

3. K2Cr2O7

3% K2Cr2O7

Formation of layers 1o alcohol no reaction 2o alcohol cloudy solution (3-5 minutes) 3o alcohol, allyl and benzyl alcohol formation of layers (separate phases) Formation of layers

RX, R2X, R3X (alkyl chloride)

RCOOH (Blue green) and CH3CH2COOH (green)

Differentiates primary from

Test

2M H2SO4

upon reacting with K2Cr2O7 Formation of colored solution (whether blue, violet, green, redbrown solution) TEST FOR PHENOLS AND ENOLS Fe(OAr)3 complex

secondary from tertiary alcohols

1. FeCl3 Test

3% FeCl3

2. Bromine water Test

Br2 in H2O

Change in color ranging from orange to black

Tribromophenols

3. Millons Test

Hg(NO3)2 in HNO3

Formation of precipitates and colored solutions ranging from red to brown

Hydroxyphenol groups

Differentiates phenols from alcohols and other organic compounds (+) test: formation of an aromatic iron complex (-) test: no change in color of solution nor formation of complex ion Differentiates phenols from alcohols and other organic compounds (+) test: formation of colored solutions (-) test: no change in the color of bromine and no change in the color of the solution of precipitate formation Detects the presence of phenols/ hydroxyl groups (phenol group in tyrosine) (+) test: formation of precipitates and colored solutions due to the presence of hydroxy group upon heating (-) test: no change in color after heating Shows the presence of a C=O of aldehyde or ketone (+) test: formation of an insoluble crystalline solid (-) test: no precipitate formation

TEST FOR ALDEHYDES AND KETONES 1. 2-4-DNPH Test 2,4Dinitrophenylhydrazine Formation of an insoluble yellow/ yellow orange solid (oily and crystalline)

2. Bisulfite Test

NaHSO3

Precipitate formation

Shows the presence aldehydes (+) test: precipitate formation (aldehydes) (-) test: no precipitate formation (ketones or other compounds)

3. Schiffs Test

Fuschine in NaHSO3 solution

Purple/violet solution

Shows the presence of aldehydes (+) test: formation of a violet solution (for aldehydes only) (-) test: no purple solution formed (ketones or other compounds)

4. Tollens Test

Ammoniacal AgNO3 solution

5. Iodoform Test

10% NaOH I2KI solution

Deposition of Silver metal to form the so called Silver mirror Formation of a solid yellow iodoform

RCHO + 2Ag(NH3)2OH 2Ag(s) + RCOOHNH4 + H2O + 3NH3

Shows the presence of aldehydes (+) test: Silver mirror (-) test: No silver mirror formed Shows the presence of CH3C=O in a molecule (+) test: solid yellow iodoform formation (-) test: no iodoform formed Differentiates reducing sugars from non-reducing sugars Shows the presence of an aldehyde (+) test: precipitate formation (Cu2O) (-) test: no precipitate formed

CH3COCH3 + 3I2 CH3COCI3 + 3HI (ketones) CH3COCI3 + OH- CHI3 + CH3COO- (aldehydes) 2 NaOH + I2 + CH3CH(OH)CH3 2 NaI + CH3COCH3 + 2 H2O (alcohols)

6. Fehlings Test

Sodium tartrate; NaOH; CuSO4

Formation of a red precipitate (Cu2O)

7. Molischs Test

-naphthol and conc. H2SO4

Formation of blue violet ring

1. C5H10O5 (pentose) + (conc.) H2SO4 C5H4O2 + 3 H2O 2. C5H4 + 2 C10H8OH (-naphthol) colored product

8. Barfoeds Test

Cu(OAc)2 in HOAc

Formation of a red precipitate (Cu2O)

Shows the presence of carbohydrates (+) test: formation of a blue-violet ring (-) test: no blue-violet ring formation Test for detecting the presence of monosaccharides (+) test: formation of a red precipitate (-) test: no precipitate formation

9. Seliwanoffs Test

Resorcinol and conc. H2SO4

Formation of a red precipitate and a pink solution

Test to differentiate aldose from ketose sugars (-) test: light pink (aldose) (+) test: red (ketose) Shows the presence of reducing sugars such as glucose, fructose, galactose, lactose and maltose. (+) tests: no precipitate green yellow orange red TEST FOR AMINES 1o Amine a trace + ++ +++

10. Benedicts Test

Sodium citrate; CuSO4; sodium bicarbonate

no precipitate green yellow orange red

a trace + ++ +++

1. Hindsberg Test

10% NaOH Benzylsulfonyl chloride

1o amines dissolves in base and precipitates from acid is a positive test. 2o amines precipitates from base and no change from acid is a positive test. 3o amines precipitates from base and dissolves in acid is a positive test.

Differentiates the different degrees of amines (+) test: 1o amines - dissolves in base and precipitates from acid is a positive test. 2o amines - precipitates from base and no change from acid is a positive test. 3o amines - precipitates from base and dissolves in acid is a positive test.

2o Amine

3o Amine

2. Nitrous acid Test

2M HCl 20% NaNO2

Evolution of gas

1o Aliphatic Amine

Differentiates the different degrees of amines 1o aliphatic amines- rapid bubbling upon addition of sodium nitrite is a positive test. 1o aromatic amines- rapid bubbling after addition of sodium nitrite (with heating) is a positive test. 2o amines- pale yellow oil with no evolution of gas is a positive test. 3o aliphatic amines- immediate positive test for nitrous acid with no evolution of gas is a positive test. 3o aromatic amines- dark-orange solution or orange solid, when treated with base turns green is a

1o Aromatic Amine

2o Amine

positive test.

3o Aliphatic Amine

3o Aromatic Amine

Amino Acid

1. Reaction of RCOOH

Methanol Concentrated H2SO4

Evolution of odor

TEST FOR CARBOXYLIC ACID AND ITS DERIVATIVES Ester

Shows the presence of an ester due to the reaction between an acid and

and ROH

2. Schotten Baumann Reaction 3. Hydrolysis of Benzamide 4. Hydrolysis of Ester

Ethanol Water Benzoyl Chloride 25% NaOH 10% NaOH Litmus paper (red)

Formation of an amides from an acyl halide and amine Change of the color of litmus paper and odor of the mixture Neutral to litmus and changes in odor RCONH2 + NaOH RCOONa + NH3 RCONHR + NaOH RCOONa + RNH2 RCONHR2 + NaOH RCOONa + R2NH RCN + NaOH + H2O RCOONa + NH3

an alcohol (+) test: evolution of odor/aroma (-) test: no evolution of odor/aroma Shows the reaction between an acyl halide and an alcohol to form an ester Shows the production of amines that can confirmed using Hinsberg test Shows the production of a carboxylic acid and an alcohol. The breaking of an ester (+) test: change in the odor of the mixture (-) test: neutral to litmus

25% NaOH

5. Hydrolysis of an anhydride

H2O

Change from blue litmus paper to red litmus paper

(RCO)2O + H2O 2RCOOH

6. Hydroxamic acid Test

7% Methanolic hydroxylamine hydrochloride solution 10% methanolic KOH 3% FeCl3

Acid Anhydride

Acyl Halide

Shows the conversion of an anhydride into a carboxylic acid (+) test: change from blue litmus to red litmus paper (-) test: no change in odor and color of the litmus paper (+) test: for RCOOH derivatives A distinct burgundy or magenta color of the ferric hydroxamate complex is a positive test. Compare the color of this solution with the yellow observed when the original compound is tested with ferric chloride in the presence of acid to assure the color is due to the formation of ferric hydroxamate complex. (+) test: for amides, amines A red to violet color constitutes a positive test. Yellow colors indicate negative tests, and brown colors or precipitates are indeterminate.

Ester

Ferric Hydroxamate Complex Formation

Nitrile

Amide

Ferric Hydroxamate Complex Formation