EXPERIMENT 10

Alcohols and Phenols

DATA and RESULTS

Properties Methanol Phenol n-butyl sec-butyl tert-butyl

Sweet Sweet and Mild Alcoholic Sharp Alcohol
Odor Alcohol Odor
Pungent Odor Tarry Odor Odor Odor
Slightly
Sol. In Water Soluble Soluble Soluble Soluble
Soluble
Phenol is only slightly soluble because it contains benzene group which is insoluble with water.
Sol. In NaOH solution Soluble Soluble Soluble Soluble Soluble
Sol. In Oil Insoluble Insoluble Insoluble Insoluble Insoluble

React in 5
minutes or Fast Reaction
more.
+ Lucas Reagent No Reaction No Reaction No Reaction
Turbid
Slow Turbid Formation
Formation

Decolorization Decolorization Decolorization Decolorization No

+ KMnO4 + dil. H2SO4
of Purple of Purple of Purple of Purple Decolorization

Esterification Observation

Production of Ethyl Ethanoate

Ethanol
Sweet Smelling (Like Pear Drops)

Production of Methyl Ethanoate

Methanol
Pleasant Smell that is similar to glues and nail polish removers

Production of Methyl Salicylate/Oil of Wintergreen

Salicylic Acid +
Smells like menthol
Methanol + H2SO4
Used for muscle or joint pains caused by strains, sprains, etc.
Chemical Reactions:

a. Lucas Reagent

Lucas Test for Alcohols

POSTLAB GUIDE QUESTIONS

1. Why is tertiary alcohol more easily oxidized in acid medium than in neutral or
alkaline medium?
Tertiary Alcohol WILL NEVER oxidized.

2. Which is a better proton acceptor, OH or –OCH2CH3? What are the relative basicities of NaOH,
sodium n-propoxide, sodium isopropoxide?
The more substituents, the more electron donor. Therefore, basicity will increase.

NAOH (Strong) > Sodium n-propoxide (Stronger) > Sodium isopropoxide (Strongest)

3. Which of the following will you predict to be more soluble in water? Give the reason for your
answer.

a.) n-hexyl alcohol or n-hęptyl alcohol

n-hexyl alcohol is more soluble because it has shorter chain than n-heptyl

b.) n-butyl alcohol or tert-butyl alcohol

tert-butyl is more soluble because it has a smaller chain than n-butyl

4. Will salicylic acid give positive result with the FeCL test? Why?

Salicylic contains benzene; benzene reacts with FeCl because FeCl is a catalyst
used in Benzene Halogenation.