Name: Regine Marie E. Espana Date Performed: Feb. 4- Feb.

8, 2011
Lab Partners: Maria Katerina Mallari Date Submitted: Feb. 15, 2011
Sharee Lou Villanueva

Experiment 7: ORGANIC DERIVATIVES OF WATER

I. Objectives

1. To be acquainted with the chemical properties of the organic derivatives of water.

2. To observe the differences in chemical reactivity of primary, secondary, and tertiary
alcohols, phenols and ethers towards selected chemical reagents.

II. Theoretical Background

Alcohols, Ethers, and Phenols are three different functional groups whose common
denominator is the presence of a singly bonded oxygen atom in their chains. 
An alcohol is any compound with an OH group (alcohol group) attached to single bonded
hydrocarbons. Ethers are two alkyl groups joined to a single oxygen. A compound which
contains a six-membered aromatic ring, bonded directly to a hydroxyl group (-OH) is called
phenol. 
The (OH) is the funclional group of alcohols and phenols. The O-H bond is polar with the
grater electron density around the oxygen atom.
Ethers are inert molecules. The ether linkage C-O-C is quite stable and can be cleared
only under drastic conditions. The unshared pairs of electrons on the oxygen atom, however,
make the ethers susceptible to electrophilic attack.

III. Data and Results

A. Solubility Behavior
 Compounds H2O NaOH H2SO4
1-butanol (n-butyl alcohol) miscible miscible -
2-butanol (sec-butyl alcohol) miscible miscible -
2-methyl-2-propanol (tert-butyl alcohol) miscible miscible -
diisopropyl ether immiscible immiscible miscible
phenol immiscible miscible -

B. Chemical Reactivity

1. Reaction with potassium permanganate

Compounds Observation
1-butanol (n-butyl alcohol) Brown precipitate

2-butanol (sec-butyl alcohol) Dark brown precipitate

2-methyl-2-propanol (tert-butyl alcohol) No precipitate (purple mixture)

diisopropyl ether No precipitate (dark brown mixture)

phenol Dark brown precipitate

2. Reaction with Tollen’s Reagent (ammoniacal silver nitrate)

Compounds Observation
1-butanol (n-butyl alcohol) brown precipitate
2-butanol (sec-butyl alcohol) dark brown precipitate
2-methyl-2-propanol (tert-butyl alcohol) light brown precipitate
diisopropyl ether brown precipitate
phenol black precipitate

3. Lucas Test: reaction with HCl-ZnCl2 mixture

Compounds Time
1-butanol (n-butyl alcohol) No reaction (miscible)
2-butanol (sec-butyl alcohol) 30 sec
2-methyl-2-propanol (tert-butyl alcohol) 15 sec
diisopropyl ether No reaction (immiscible)
 phenol No reaction (miscible)

4. Reaction with ferric chloride (FeCl3)

Compounds Observation
1-butanol (n-butyl alcohol) No reaction (yellow)
2-butanol (sec-butyl alcohol) No reaction (yellow)
2-methyl-2-propanol (tert-butyl alcohol) No reaction (yellow)
diisopropyl ether No reaction (yellow)
phenol Dark yellow (brown) mixture

5. Iodoform Test: reaction with I2, NaOH

Compounds Observation
1-butanol (n-butyl alcohol) Immiscible (smell similar to very stong acetone),
no reaction
2-butanol (sec-butyl alcohol) miscible (cloudy yellowish precipitate, smell
similar to acetone)
2-methyl-2-propanol (tert-butyl alcohol) miscible (smell similar to commrcial betadine), no
reaction
diisopropyl ether Immiscible (smell similar to acetone)
phenol miscible (smell similar to commercial paste)

IV. Discussion

The different samples that were tested by solubility of water do not contain
the same result. There are factors that may have caused them to be insoluble. Basically, alcohols are
insoluble in water except if they are in Carbon-6. Like dissolves like, therefore, a compound that is in a
polar function group is more soluble in water. Also, the more branching is present in a compound, the
more it will be soluble.
 Phenol dissolves in aqueous sodium hydroxide because phenol behaves as an acid and gives up
its proton to the hydroxide ion which is a base. A soluble ionic product is then formed. In this reaction,
the hydrogen ion has been removed by the strongly basic hydroxide ion in the sodium hydroxide solution.
Diidopropyl ether was known to be soluble only with H2SO4.

Bayer's reagent (KMnO4) is an alkaline solution of potassium permanganate, which is a powerful

oxidant. This reagent is used for oxidation (Bayer’s Oxidation).
Reaction with double or triple bonds i n a n   o r g a n i c m a t e r i a l c a u s e s   t h e c o l o r
t o   f a d e   f r o m   p u r p l i s h - p i n k   t o   b r o w n . T h e disappearance of the purple color and the
appearance of a brown precipitates concludes that it is a positive test. Often, the brown
precipitate fails to form and the solution turns reddish-brown.

In the experiment, 2-methyl-2-propanol (tert-butyl alcohol) produced no brown precipitate and

retained its violet color. Diisopropyl ether produced no precipitate bu changed its color from violet to
brown.

The reaction with Tollen’s reagent give positive results only for easily oxidizable
compounds(aldehyde) and gives ngative results for ketones.

V. Answers to Questions