Analysis of

Oxygen Bearing
Organic
Compounds
Birung, De Leon, Gatdula,
Joquico, Mallari

Keywords
Alcohol
Aldehyde
Ketone
Ester
Carboxylic Acid
Dichromate Test
Tollens Test
Lucas Test
DNPH Test
Hydroaxamic Acid Test
Iodoform Test

Objectives
Differentiate

the various types of

oxygen-bearing organic compound
Device a scheme to distinguish each
functional group
Characterize an unknown sample
through parallel chemical tests

Functional Groups
Alcohols

n- Propanol
2- Propanol
Butanol

Ketones

Acetone

Aldehydes

Formaldehyde

Esters

Ethyl Acetate

Introduction

n- Propanol
primary alcohol
CH3CH2CH2OH
colorless liquid
Molar mass: 60.09 g/mol
Polar solvent
cleaning fluid, adhesive and stain
remover, preservative

2- Propanol
Isopropyl

Alcohol
C3H8O or C3H7OH / CH3CHOHCH3
colorless,

flammable chemical
compound with a strong odor
secondary alcohol
Boiling point: 82.6 C
Molar mass: 60.1 g/mol

2-Butanol
secondary alcohol
CH3CH(OH)CH2CH3
flammable, colorless liquid
Polar Solvent
Molar mass: 74.122 g/mol
Boiling point: 98 to 100 C

Formalin
Formaldehyde

CH2O
gas at room temperature
colorless and has a characteristic
pungent, irritating odor
nail hardeners and/or nail varnish
Boiling point: -19 C
Molar mass: 30.031 g/mol

Acetone
propan-2-one
(CH3)2CO
colorless,

volatile, flammable liquid

simplestketone
Polar Solvent
active ingredient in nail polish remover and
as paint thinner.
Boiling point: 56C
Molar mass: 58.08 gmol1

Ethyl Acetate
C4H8O2
colorless liquid, characteristic sweet
smell
glues, nail polish removers,
decaffeinating tea and coffee, and
cigarettes
ester of ethanol and acetic acid
Polar solvent

Chemical Tests
Used in the
Experiment

Dichromate Test
Used

to distinguish between primary,

secondary, and a tertiary alcohol.

Primary alcohol- oxidized to adehydes and then

further oxidized to carboxyllic acid
Sencondary alcohol-oxidized to ketones
Tertiary alcohol- not oxidized

R-CH2(OH) R-CO-OH
R-CH(OH)-R
R-CO-R

Tollens Test

Also called silver-mirror test

Uses Tollens reagent which contains silver ions
coordinated to ammonia [Ag(NH3)2OH]
Used to distinguish between an aldehyde and a ketone
Tollens reagent oxidizes aldehydes to ammonium salts
of carboxyllic acid
R-CHO

R-COO-NH4+

This reaction is accompanied by the reduction of silver

ions which in turn forms the silver mirror coat observed
in the test tube.

Lucas Test
Uses Lucas reagent which is an aqueous
solution of a strong acid (HCL) and zinc
chloride.
A substitution reaction where the chloride of
the zinc chloride is replaced by the hydroxyl
group of the alcohol takes place
Used to classify alcohols in accordance with
their reactivity

Primary- no visible reaction

Secondary- solution turns turbid in 5-20 minutes
with heating
Tertiary- solution turns turbid rapidly and forms
two layers

The formation of turbid solutions happens

because of the formation of a
chloroalkane
R-OH R-Cl

The reaction only happens when the

alcohols used are soluble in the Lucas
reagent

DNPH Test
DNPH stands for dinitrophenylhydrazine
Used to qualitatively detect the carbonyl
group functionality in aldehydes and ketones
Positive result is a yellow or red precipitate
known as the dinitroprhenylhydrazone
It is a condensation reaction where two
molecules join and lose water

R-CO-R

R-C-R

Iodoform Test
Used to identify methyl ketones
NAOCl oxidizes a methylcarbonyl group
When iodoform is liberated from the
mixture, it forms a yellow precipitate which
indicaes that a reaction has occured
Only ethanal aldehyde and methyl ketones
can undergo this reaction

R-CO-CH3

R-COO- + CH3I

Hydroxamic Acid Test

Test

for esters, whereby the ester is

converted to a hydroxamic acid
A positive result is a red-purple solution
If the prior tests do not identify a
sample as an aldehyde or ketone, then
the sample could be an ester.

Methodology

Birung, Adriel T.

Chemical Tests

Reaction 1: Dichromate Test

Reaction 2: Tollens Test

Reaction 3: Lucas Test

Reaction 4: DNPH Test

Reaction 5: Iodoform Test

Reaction 6: Hydroaxamic Test

Birung, Adriel T.

Dichromate Test

Dichromate oxidizes primary/secondary

alcohols and aldehydes to ketones or
carboxylic acids.

R-CH2 (OH) R-CO-OH

R-CH(OH)-R

Green solution

R-CO-R

Tollens Test
Tollens

reagent [Ag(NH3 )2 OH] oxidizes

aldehydes to ammonium salts of
carboxylic acids

R-CHO

R-COO- NH4+

Silver mirror coat

Lucas Test

Alcohols are converted to alkyl

chlorides with ZnCl2

R-OH

R-Cl

Turns turbid fast

DNPH Test

DNPH reagent condenses with carbonyl

containing molecules

R-CO-R

Red-orange ppt

R-C-R

Iodoform Test

NaOCl oxidizes a methylocarbonyl

group and in the process yield a yellow
ppt of iodoform

R-CO-CH3

Yellow ppt

R-COO- + CH3

Hydroaxamic Test
Hydrogen peroxide reacts with aromatic
primary amides to form the hydroxamic
acid, which then reacts with ferric
chloride to form ferric hydroxamate
complex having a purple color
Purple ppt

Unknown Sample
Dichromate Rxn
DNPH Rxn

No
Green sol?

Non-Oxidizable

Yes

No
Red orange
ppt?

3o Alcohols

Yes
Ketones

Oxidizable
Tollens Rxn
No
Mirror
coat?
Yes
Aldehydes

Lucas Rxn.
1 or 2 Alcohol
o

Turbid fast?
Yes
2o Alcohols

No

1o Alcohols

RESULTS

Group 1 & 2

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
is Acid
Test

n-Propanol

Blue green
solution

Colorless
solution

Colorless
solution

Orange
solution

Colorless
solution
with white
precipitate

Really light
yellow
solution

2-Propanol

Blue green
solution

Colorless
solution

Colorless
solution

Orange
solution

Colorless
solution
with white
precipitate

Colorless
solution

3-Butanol

Orange
solution

Colorless
solution

Cloudy

Yellow
precipitate
in orange
solution

Red
bubbles in
UL rusting
yellow
solution

Colorless
solution

Formalin

Blue green
solution

Grey
precipitate
(mirror)
solution

Colorless
solution

Yellow
precipitate
in orange
solution

Colorless
solution

Colorless
solution

Acetone

Orange
solution

Colorless
solution

Colorless
solution

Yellow
precipitate
in orange
solution

Colorless
solution

Colorless
solution

Ethyl
Acetate

UL- Light
orange
LL- orange

Colorless
solution

Colorless
solution

Orange
solution

UL-reddish
black
LL- Goldenlike with

Colorless
solution

Groups 3 & 4

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
ic Acid
Test

n-Propanol

Blue
solution

Colorless
solution

Colorless
solution

Orange
solution

White
precipitate
in light
yellow
solution

Light
brownish
yelllow
solution

2-Propanol

Blue
solution

Oil-like
substance
in colorless
solution

Colorless
solution

Orange
solution

Yellow
precipitate
in colorless
solution

Yellow
solution

3-Butanol

Brownish
orange
solution

Colorless
solution

Light
yellow
solution

Orange
precipitate
in yellow
solution

Black
precipitate
in brown
solution

Bright
yellow
solution

Formalin

Blue-green
solution

Silver
precipitate
in colorless
solution

Colorless
solution

Yellow
precipitate
in yellow
solution

White
precipitate
in colorless
solution

Yellow
solution

Acetone

Orange
solution

Colorless
solution

Colorless
solution

Orange
precipitate
in yellow
solution

Yellow
precipitate
in colorless
solution

Orange
precipitate
in orange
solution

Ethyl
Acetate

Orange
solution

Colorless
solution

Light-green
solution

Orange
solution

Red-orange
upper
layer,
orange

Blood red
solution

Groups 5 & 6

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
ic Acid
Test

n-Propanol

Blue green
solution

Colorless
solution

2 layers,
clear and
colorless

Orange
solution

Colorless
solution

Colorless
solution;
orange
precipitate

2-Propanol

Blue-green
solution

Colorless
solution

2 layers;
clear and
colorless

Orange
solution

Colorless
solution

Colorless
solution;
orange
precipitate

3-Butanol

Orange
solution

Colorless
solution

2 layers;
turbid

Orange
solution;
orange
precipitate

Red-orange
solution;
brown
precipitate

Colorless
solution;
orange
precipitate

Formalin

Blue green
solution

Gray
precipitate
cloudy
white
solution

Colorless
solution

Yellow
solution;
yellow
precipitate

Colorless
solution

Yellow
solution

Acetone

Orange
solution

Colorless
solution

Colorless
solution

Orange
solution;
orange
precipitate

Colorless
solution

Yellow
solution

Ethyl
Acetate

Blue green
solution

Colorless
solution

Colorless
solution

Orange
solution

Orange
solution
with red

Red
solution

Group 7 & 8

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
ic Acid
Test

n-Propanol

Blue-green
solution

Colorless,
no
precipitate

No layers,
no turbidity

Yellow
solution

Colorless
solution

Yellow
solution

2-Propanol

Blue-green
solution

Colorless,
no
precipitate

No layers,
no turbidity

Yellow
solution

Colorless
solution

Yellow
solution
with redorange
precipitate

3-Butanol

Orange
solution

Colorless,
no
precipitate

Turbid

Red-orange
precipitate

Orange
solution

Yellow
solution

Formalin

Blue-green
solution

Metallic
silver
precipitate
in colorless
solution

No layers.
No
turbidity

Yellow
solution
with yellow
precipitate

Colorless
solution

Red-orange
solution

Acetone

Orange
solution

Colorless,
no
precipitate

No layers,
no turbidity

Yellow
solution
with yellow
precipitate

Colorless
solution
with green
precipitate

Yellow
solution
with redorange
precipitate

Ethyl
Acetate

Orange
solution;
after 15
mins,

Colorless,
no
precipitate

No layers,
no turbidity

Dark yellow Dark yellow Dark red

solution
lower layer solution
and redorange

Group 9 & 10

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
ic Acid
Test

n-Propanol

Dark blue
green
solution

Colorless

Colorless

Orange
solution

Colorless

UL-Dark
yellow
LL-colorless

2-Propanol

UL- Blue
green
LLColorless

Colorless

Colorless

Orange
solution

Colorless

Light
yellow
solution

3-Butanol

Light
orange
solution

Gray
precipitate
in colorless
solution

UL-Turbid
LLColorless

Orange
precipitate
in orange
solution

Dark red
precipitate
in orange
solution

UL- Yellow
solution
LLColorless
solution

Formalin

Light blue
green
solution

Silver
mirror
solution

Colorless

Yellow
precipitate
in yellow
solution

Colorless

Light
reddish
brown
solution

Acetone

Orange
solution

Colorless

Colorless

Orange
precipitate
in orange
solution

Yellow
green
precipitate
in colorless
solution

UL- Light
yellow
solution
LL- Cloudy
orange
solution

Ethyl
Acetate

UL- Cloudy
orange
solution

colorless

Colorless

Orange
solution

UL- orange
solution
LL-Light

Red violet
solution

Summary

Dichromat
e Test

Tollens
Test

Lucas Test

DNPH Test Iodoform

Test

Hydroxam
ic Acid
Test

n-Propanol

Blue green
solution

Colorless
solution

Colorless
solution

Orange
solution

Colorless
solution

Yellow
solution

2-Propanol

Blue-green
solution

Colorless
solution

Colorless
solution

Orange
solution

Colorless
solution

Colorless/Y
ellow
solution

3-Butanol

Orange
solution

Colorless
solution

Turbid

Orange
precipitate
in orange
solution

Brown
precipitate
in orange
solution

Yellow
solution

Formalin

Blue-green
solution

Silver
precipitate
in colorless
solution

Colorless
solution

Yellow
precipitate
in yellow
solution

Colorless
solution

Yellow
solution

Acetone

Orange
solution

Colorless
solution

Colorless
solution

Orange
solution in
orange
precipitate

Yellow/gree
n
precipitate
in colorless
solution

Orange
precipitate
in orange
solution

Ethyl
Acetate

Orange
solution

Colorless
solution

Colorless
solution

Orange
solution

UL- Redorange
LL- orange

Dark red
solution

Sources of Error:
Contamination

of reagents due to
chemical remains from previous
experiment
Medicine droppers were contaminated
due to being used twice or more in
different chemicals
Insufficient or excess amount of heat in
some tests

Conclusions:

Objectives:

Differentiate the various types of oxygen-bearing organic

compound
Device a scheme to distinguish each functional group
Characterize an unknown sample through parallel chemical
tests

Primary alcohol
Secondary alcohol
Tertiary alcohol
Aldehyde
Ketone

References
http://www.organicchem.org/alcohols/react

ions_of_alcohols/the_oxidation_of _alcohols
http://www.chemguide/carbonyls/addeli
m.html
http://www.chemguide/carbonyls/iodoform.
html
http://www.reagenssi.kemia.helsinki.fi/netti
labria/tiedostot/introductory_course_analys
is.pdf