Classification test of organic

compounds

mrsantiago (Chem 200 lab, AY 2014-2015)

Physical and chemical properties

Physical properties
Physical state (solid, liquid, gas)
Color, odor
Solubility
Chemical properties
Reaction to litmus paper
Chemical tests
mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in water

mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

Factors affecting H2O solubility

Intermolecular forces of attxn
(H bonding>dipole>hydrophobic)
No. of carbon atoms (>5C insoluble; C,
hydrophobicity, less polar )

Length of HC chain
Branching (branching, length, hydrophobic)
Presence of polar functional groups
mrsantiago (Chem 200 lab, AY 2014-2015)

FUNCTIONAL GROUPS THAT MAY

CAUSE IMFA
Functional groups that can participate in H-bonding

Carboxyl
Carbonyl
Hydroxyl
Amino

Functional groups that can participate Dipole-Dipole Interaction

Hydroxyl
Amino
Halo
Mercapto
Carbonyl
Carboxyl

Functional groups that can participate in hydrophobic interaction

hydrocarbon
mrsantiago (Chem 200 lab, AY 2014-2015)

ACID AND BASE

Bronsted Acid and Bases
Acid: proton donor
Base: proton acceptor

Lewis Acid and Bases

Acid: e- acceptor
Base: : e- donor

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in 5% HCl

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in 5% HCl
Basicity
Availability of electron pairs
(the more available the electrons, the more
readily they can be donated to form a new bond
to the proton and, the stronger base)
Electronegativity ( CH3- > NH2- > HO- > F-)
the more e- the atom donating the electrons , the
less willing it is to share those electrons with a
proton, so the weaker the base.
mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in 5% HCl
Size (F- > Cl- > Br- > I- )
the larger the atom the weaker the H-X bond
and the lower the electron density making it a
weaker base
Resonance (RO- > RCO2- )
electrons less available when they localised on a
specific atom

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in 5% NaOH
ACIDITY
Electronegativity (HF > H2O > NH3 > CH4 )
the more electronegative the anionic atom in
the conjugate base, the better it is at accepting
the negative charge, stronger acid.
Size (HI > HBr > HCl > HF)
The size weakens the bond H-X, weaker acid
Resonance (RCO2H > ROH)
mrsantiago (Chem 200 lab, AY 2014-2015)

Acidity trend of common organic acids

and bases

mrsantiago (Chem 200 lab, AY 2014-2015)

Summary (Expt 6)
Sample

Physical state Solubility in

H20

Solubility in
HCl (Basic)

Solubility in
NaOH (Acid)

Cyclohexane

L (gas-like)

Dichloromethane L (Cl-like)

Ethanol

l (wine-like)

Phenol

l (pungent

Benzoic acid

s (pungent)

+ (wa)

Ethyl acetate

l (plastic
balloon-like)

Ethyl amine

l(fish-like)

mrsantiago (Chem 200 lab, AY 2014-2015)

FLAMMABILITY/COMBUSTIBILITY OF
ORGANIC COMPOUNDS
Complete Combustion:
CxHy + O2 CO2 + H2O
Incomplete Combustion:
CxHy + O2 CO2 + CO +
C + H2 O
C:H ratio,
combustible,
luminosity, soot

Sample

Flammability
(C:H)

Hexane

6:14

Heptane

7:16

Cyclohexane

6:12

Cyclohexene

6:10

Benzene

6:6

Toluene

7:8

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in conc. H2SO4

mrsantiago (Chem 200 lab, AY 2014-2015)

Solubility in conc. H2SO4

mrsantiago (Chem 200 lab, AY 2014-2015)

mrsantiago (Chem 200 lab, AY 2014-2015)

TEST FOR ACTIVE UNSATURATION

Immediate reaction to halogenating
substances such the diatomic halogen
compounds (Br2, Cl2, I2 and F2)
Easily oxidized to saturated HC
Order of oxidation of HC: Alkyne Alkene Alkane

Tests for Active Unsaturation:

Br2 Test
Baeyers Test
mrsantiago (Chem 200 lab, AY 2014-2015)

1. BROMINE TEST (AE)

Rgt: Br2 in DCM solution
+ Result: decolorization of Br2 in DCM

mrsantiago (Chem 200 lab, AY 2014-2015)

2. BAEYERS TEST (REDOX)

Rgt: Aqueous KMnO4
+ Result: decolorization of KMnO4 and brown ppt.

mrsantiago (Chem 200 lab, AY 2014-2015)

Summary: Test for Active Unsaturation

Sample

Baeyers

Br2 in DCM

Hexane

-(slow)

Heptane

-(slow)

Cyclohexane

-(slow)

Cyclohexene

+++ (fast)

+++ (fast)

Benzene

Toluene

- (slow)

- (slow)

mrsantiago (Chem 200 lab, AY 2014-2015)

AROMATICITY HYDROCARBONS
(HUCKLES RULE)
1.
2.
3.
4.

Cyclic
Planar
Conjugated double bonds
#e- = 4n + 2, where n I

mrsantiago (Chem 200 lab, AY 2014-2015)

TEST FOR AROMATICITY

Nitration of the aromatic ring
Preparation of Nitrating Agent:
HNO3 + H2SO4 NO2+ + 2HSO4- + H3O+
Prevents dilution of NO2+ by absorbing water in the mixture

Nitration of the Aromatic Ring (SE)

mrsantiago (Chem 200 lab, AY 2014-2015)

Test for arenes: BASIC OXIDATION

TEST
Test for arenes (alkylbenzene)
Oxidation of alkyl group to COOH

mrsantiago (Chem 200 lab, AY 2014-2015)

Summary (Expt 7)
Sample

Flamma
bility
(C:H)

Solubility
in H2SO4

Baeyers

Br2 in DCM Nitration

Hexane

6:14

-(slow)

Heptane

7:16

-(slow)

Cyclohexane

6:12

-(slow)

Cyclohexene

6:10

+
+++ (fast)
(alkene/alk
yne)

+++ (fast)

Benzene

6:6

+++ (fast)

Toluene

7:8

- (slow)

- (slow)

+++ (fast)

Basic
Oxidation

+++ (fast)

- (slow)

mrsantiago (Chem 200 lab, AY 2014-2015)