ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY © GIDEON A. LEGASPI, SUSAN T. STA.

ANA 2009

EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER

Alcohols can be classified based on the number of alkyl groups attached to the carbon that contains the
hydroxyl group as illustrated below.

Each type of alcohol has different reactivity towards various reagents. Primary and secondary alcohols
react with various oxidizing agents while tertiary alcohols are unreactive. On the other hand, tertiary alcohols are
most reactive to nucleophilic substitution in Lucas reagent while secondary alcohols are quite reactive and
primary alcohols are unreactive. The presence of benzene ring makes phenol more acidic than comparable cyclic
and acyclic alcohols. Phenols are oxidized only by the strongest oxidative agents. A useful chemical test for
differentiating phenols from alcohols is via ferric chloride test. Ethers are generally unreactive as it is a very stable
bond.

Objectives
In this experiment, you will be able to distinguish the difference among various organic derivatives of
water based on their characteristic solubility behavior and reactions. Using this knowledge, you will understand
how to identify unknown samples of alcohols, phenols, or ethers.

Materials and Reagent

95% Ethanol Unknown sample 1 Lucas reagent Test tubes
2-Butanol Unknown sample 2 1% Ferric chloride Pasteur pipettes
tert-butanol Unknown sample 3 Distilled water
Phenol Bayer’s reagent 1.00M NaOH
Diethyl ether 1.00M Na2Cr2O7 Conc. H2SO4

Procedures

PRECAUTIONS: Phenol, concentrated sulfuric acid, sodium dichromate, and NaOH are corrosive substances.
Avoid direct skin contact. Diethyl ether vapour is toxic, avoid inhalation.

1. Place 5 drops 1-butanol, 2-butanol, tert-butanol, phenol, diethyl ether, and each of the unknown samples on
separate dry test tubes. Prepare new set of samples for each of the test below:
a. Solubility in water– add 5 drops of distilled to each sample. Shake and then observe solubility.
b. Solubility in NaOH – add 5 drops of NaOH to each sample. Shake then observe solubility.
c. Bayer’s oxidation – add 5 drops of Bayer’s reagent. Shake and observe the reaction.
d. Chromic acid oxidation – add 5 drops of Na2Cr2O7 and 3 drops of conc. H2SO4. Observe the reaction.
e. Lucas test – add 10 drops of Lucas reagent. Shake and observe the reaction for about 5-10 minutes.
f. Ferric chloride test – add 5 drops of ferric chloride. Shake and observe the reaction.
2. Identify the unknown samples by comparing their solubility and reaction profile against that of the known
compounds
1
ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY © GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009

SCHEMATIC DIAGRAM

EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER

2
ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY © GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009

DATA SHEET

EXPERIMENT #5: ORGANIC DERIVATIVES OF WATER

NAME:________________________________________________________________ SCORE:_________

SECTION:______ DATE PERFORMED:____________ INSTRUCTOR:_____________________________

A. Solubility and Reaction Profile (30pts)

Solubility in Solubility Bayer’s Chromic acid Lucas test Ferric

H2O in NaOH oxidation oxidation chloride test
Visible + result
SAMPLES
Ethanol
2-Butanol
tert-Butanol
Phenol
Diethyl ether
Unknown 1
Unknown 2
Unknown 3
Legend: ++  fast reaction/completely soluble; +  slow reaction/slightly soluble; -  no reaction/insoluble

Identities of Unknown Samples

Sample 1:___________________________
Sample 2:___________________________
Sample 3:___________________________

B. Pertinent General Reactions (20 pts)

(1) Bayer’s oxidation:

(2) Chromic acid oxidation:

(3) Lucas test

3
ESSENTIALS OF ORGANIC CHEMISTRY LABORATORY © GIDEON A. LEGASPI, SUSAN T. STA. ANA 2009

(4) Ferric chloride test

C. Follow-up Questions and Applications (20 pts)

1. Explain why phenols are more acidic than comparable cyclic and acyclic alcohol and why is it resistant to weak
oxidizing agents? (3 pts)

2. What is the reason why tertiary alcohols cannot be oxidized? (2 pts)

3. Illustrate the mechanism for the nucleophilic substitution of tertiary alcohols with Lucas reagent. (5 pts)

4. Give some economic uses of alcohols, phenols, and ethers. (5 pts)

5. What are polyphenols and how do they protect against many degenerative disease such as cancer,
Alzheimer’s disease, and cardiovascular diseases? (5 pts)