Experiment 9 (Classification Tests For Hydroxy and Carbonyl Hydrocarbon Derivatives)

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CLASSIFICATION TEST

FOR HYDROXYL AND CARBONYL


CONTAINING HYDROCABON
DERIVATIVES

HYDROXYL CONTAINING
HYDROCARBON DERIVATIVES

CHARACTERISTIC OF THE -CARBON


AND ACIDITY OF ALCOHOLS

SOLUBILITY OF ALCOHOLS IN WATER

Polar hydroxyl group


Non-polar/hydrophobic hydrocarbon chain
#C, hydrophobic, polar, soluble in H2O
branched, hydrophobic, soluble in H2O

Solubility in water:

30 > 20 > 10 >

NUCLEOPHILIC SUBSTITUTION OF
ALCOHOLS

CARBONYL CONTAINING
HYDROCARBON DERIVATIVES

OXIDATION OF ALCOHOLS AND


ALDEHYDES

No rxn

No rxn

LUCAS TEST
Differentiating test for 10, 20 and 30 ROH
Based on SN1 reaction
Lucas Reagent:
ZnCl2 in HCl

CHROMIC ACID TEST


(JONES OXIDATION TEST)
Differentiating test for oxidizable carbons

No Reaction

CHROMIC ACID TEST


(JONES OXIDATION TEST)

2,4-DNPH TEST
Test for presence of carbonyl group
formation of hydrazone

Reagent: 2,4-dinitrophenyl hydrazine

Can be used to differentiate aromatic and


aliphatic carbonyl containing organic compound
Aromatic: red orange ppt
Aliphatic yellow orange ppt

2,4-DNPH TEST

2,4-DNPH TEST

FEHLINGS TEST
Test for oxidizable carbon
Differentiating test for RCOH and R1COR2

Components:
Fehlings A: CuSO4(aq)
Fehlings B: potassium sodium tartrate, NaOH

No rxn

FEHLINGS TEST

TOLLENS (SILVER MIRROR) TEST


Test for oxidizable carbon
Reduction of Ag+ to Ag

No rxn

TOLLENS (SILVER MIRROR) TEST

IODOFORM TEST
Test for methyl carbonyl
Enolate formation of methyl carbonyl group
Reagent: 10% KI/NaClO

IODOFORM TEST

Test Sample
n-butyl alcohol
sec-butyl alcohol
tert-butyl alcohol
acetaldehyde

n-butyraldehyde
benzaldehyde
acetone
acetophenone
Isopropyl alcohol

Lucas Test

Chromic Acid Test

2,4-DNPH Test

Test Sample
n-butyl alcohol
sec-butyl alcohol
tert-butyl alcohol
acetaldehyde

n-butyraldehyde
benzaldehyde
acetone
acetophenone
Isopropyl alcohol

Fehlings Test

Tollens Test

Iodoform Test

THANK YOU

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