Investigation of solid organic compounds

General reactions.

1) Element test for N,S&Cl

2) Acidity test. Acidic or nonacidic character
3) Nitration test. Aromatic , Aliphatic
4) Heat on porcelain test. Aromatic , Aliphatic or carbohydrates
5) Metallic residue test. Metallic salt or nonmetallic salt.

6) Test with FeCl3 a) phenolic group [Red, Violet, green color or ppt.]
b) Salt of aromatic acids [phthalate, benzoate or cinnamate ] Buff ppt.
c) Acetate or formate [Red color by heat converted to Brown ppt.]

7) Test with NaOH a) Insol. In H2O &sol. In NaOH.
b) Sol. In NaOH & darkness.
c) Odor of ammonia on cool
d) Odor of ammonia by heat
e) Brown color with heat
*Aromatic acid or insol. Phenol.
* di or tri phenolic group.
*Amm. Salt.
*Amide,Imide or urea.
*Carbohydrates.

8) Test with sod.lime a) Odor of ammonia *Amm. Salt, Amide, Imide or urea.
b) Odor of burnt sugar *Carbohydrates.
c) Odor of benzene * benzene carboxylic acid
d) Odor of phenol *Phenolic carboxylic acid.

9) Solubility &revers perciptate.

*If the compound insoluble in water.
a) Soluble in NaOH &reperciptate by HCl *Acidic compound.
b) Soluble in HCl&r eperciptate by NaOH *Basic compound.
c) Insoluble in water,HCl&NaOH. * Insoluble neutral.

Combination of [C, H, O]
1) Molish test for [Carbohydrates]. Violet ring.
a) Iodine test for [poly saccaried]. Blue color. *Starch
b) Fehling test [Reducing or nonreducing] Brown ppt *reducing
-ve * nonreducing EX: Sucrose (di).
b*) Amm.Silver nitrate test [Reducing or nonreducing] Grey ppt *reducing
-ve *non reducing
c) Barfoid test [mono or di] Red color *mono
-ve *di
c*) Osazone test [mono or di] Yellow crystals on hot *mono
Yellow crystals after cooling *di
 2) Test for carboxylic group (-COOH) . [Acidity test] Give Effervescence.

a) Aliphatic acids:
COOH CH(OH)COOH CH2COOH CH2COOH

COOH CH(OH)COOH C(OH)COOH CH2COOH

CH2COOH

i) Oxalic Acid. ii) Tartaric Acid. iii) Citric Acid. iv) Succinic acid.

b) Aromatic acids:

COOH COOH COOH

CH=CHCOOH

COOH OH

i) Phthalic acid ii) Benzoic acid iii) cinnamic acid iv) Salicylic acid

3) Test for Metallic salts. [Metallic residue test]. Give Effervescence

a) Of Aliphatic Acids.
COONa CH(OH)COONa CH2COONa CH2COONa

COONa CH(OH)COONa C(OH)COONa CH2COONa CH3COONa HCOONa

CH2COONa

i) Sod.Oxalate. ii) Sod.Tartarate. iii) Sod.Citrate. iv)Sod. Succinate. v) Sod.Acetate. vi)Sod.

Formate.

b) Of Aromatic Acids.

COONa COONa COONa

CH=CHCOONa

COONa OH

i) Sod.Phthalate ii) Sod.Benzoate. iii) Sod.cinnamate . iv) Sod.Salicylate.

4) Test for phenolic group (OH). [With FeCl3] Give one of the color bellow the structures.
a) Soluble phenols.
OH OH OH OH

OH
OH

OH OH

OH

i) Catechol ii) Resorcinol. iii) Quinol iv) Pyrogallol.

Solution + FeCl3 Green color. Violet color. Green ppt. Red color.

b) Insoluble phenols.
OH

OH

Solution (alc.) + FeCl3 Violet color. Green color.

5) Test for aldehydic group (-CHO) [Shiff test] give pink color.

6) Test for ketonic group (C=O) [With2,4 dinitrophenylhydrazine] give Orange crystals.
O

Benzobhenone.

7) Test for hydrocarbon group (C ,H) [Picrate test by picric acid] give Yellow or Red crystals.

Naphthalene Anthracene.

8) Test for alkene group (C=C) [unsaturation test] give decolorisation for KMno 4&Br2/H2O.

Ex: Sod.cinnamate , Amm.cinnamate & Cinnamic acid.

 Combination of [N]
1) Grind test [for Amm.salts] Give Odor of ammonia.

a) Of Aliphatic Acids.
CH2COONH4

COONH4 CH(OH)COONH4 C(OH)COONH4 CH2COONH4

COONH4 CH(OH)COONH4 CH2COONH4 CH2COONH4 CH3COONH4 HCOONH4

i) Amm.Oxalate. ii) Amm.Tartarate. iii) Amm.Citrate. iv)Amm.Succinate. v) Amm.Acetate. vi) Amm. Formate.

b) Of Aromatic Acids.

COONH4 COONH4 COONH4

CH=CHCOONH4

COONH4 OH

i) Amm.Phthalate ii) Amm.Benzoate. iii) Amm.cinnamate . iv) Amm.Salicylate.

2) Hydrolysis with NaOH [for Amide,Imide &Urea]. Give Odor of ammonia

a) Aliphatic:
NH2CONH2

Urea
*Burit test (Urea) Purple color.

O O

HO C C
CONH2 CH H2C
NH NH CH3CONH2

CONH2 CH C H 2C C
HO
O O

i)Oxamide ii)Tartarimide iii)Succinimde iv)Acetamide

b) Aromatic:
O

C CONH2 CONH2
CH=CHCONH2

NH

C OH

i)Phthalimide ii)Benzamide iii)Cinnamamide iv) Salicylamide.

3) Azo-dye test [for primary amine]. Give from orange to reddish brown dye.

NH2 NH2 NH2

NH2
COOH

CH3

i) P-Toludine ii)Anthranilic acid iii)α-naphthyl amine iv)β-naphthyl amine.

4) Aniline blue test [for secondary amine]. Give blue color.

H
N

Diphenylamine

5) Azo-dye after reduction [for nitro group]. Give red dye

a) In presence of amino group.

NH2 N N Cl OH

HCl/NaNO2 H2O/boil
Give -ve Azo-dye

NO2 NO2 NO2

Then Reduction step:

OH OH

HCl/Zn, boil
Give +ve Azo-dye

NO2 NH2
 b) In absence of amino group.

The Reduction step only:

CH3 CH3

HCl/Zn, boil
Give +ve Azo-dye

NO2 NH2

6) Hydrolysis with 70% H2SO4 [for anilide group]

NH2 COOH
H
N O
C
70% H2SO4
+

Benzanilide Aniline Benzoic acid

NH2
H
N O
C
70% H2SO4
+ CH3COOH
CH3

Acetanilide Aniline Acetic acid