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Lab Alcohols

Objectives:
 Study the physical and chemical properties of alcohols.
 Identify known compounds as alcohols.

Introduction:
An alcohol is defined as an organic compound having a hydroxyl group attached to carbon. But
this carbon can not be a carbonyl carbon, meaning this carbon is not doubly bonded to an
oxygen. See the below structures and nomenclature.

general
R OH
structure

H H
example
H C C OH
structure
H H

IUPAC
ethanol
nomenclature

common
ethyl alcohol
nomenclature

An alcohol’s properties are dependant upon the structure of the molecule it is bonded to. The
different structures are classified as follows:

A primary carbon is bonded to one other carbon, both of these carbons are primary carbons.
H H
H C C H
H H
A secondary carbon is bonded to two other carbons, the red carbon is a secondary carbon.
H H H
H C C C H
H H H
A tertiary carbon is bonded to three other carbons, the red carbon is a tertiary carbon.

1
H
H C H
H H
H C C C H
H H H

Knowing these if we replace one hydrogen with a –OH group we get the following:
1, primary alcohol has –OH group bonded to a carbon which is bonded to one other carbon:
H H
H C C OH
H H
2, secondary alcohol has –OH group bonded to a carbon which is bonded to two other carbon:
H OH H
H C C C H
H H H
3, tertiary alcohol has –OH group bonded to a carbon which is bonded to three other carbon:
H
H C H
H H
H C C C H
H OH H
The classification dictates what types of reactions the alcohol will undergo. And allows a person
to test a liquid and determine which type of alcohol is present.

Alcohols of small molecules will be soluble in water. For example, the two carbon compound
ethanol is completely miscible in water. This is due to the polar nature of a hydroxyl group
where hydrogen bonded occurs with the water molecule. But when the molecule is composed
of more carbons, the non-polar nature of the hydrocarbon tail will cause the structure to be
insoluble.

There are many test reagents used in the determination of alcohol functional groups. Ceric
nitrate solution is created by adding nitric acid to ammonium nitrate. This solution reacts with
the hydroxyl group to qualify a sample as an alcohol. The Lucas reagent is a solution
composed of HCl and ZnCl2. The Lucas reagent is used to determine the classification of an
alcohol, primary, secondary or tertiary. Chromic acid, a strong oxidizing agent, is made by
adding chromium trioxide to sulfuric acid. This reagent is also used to determine the
classification of an alcohol. The I2-KI reagent, formed by adding I2 and KI to water. This reagent
will give a positive test for a hydroxyl group bonded to a carbon which is also bonded to a
methyl group, -CH3.

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Procedure:
Your observations are the most important aspect of this lab. Remember to be as descriptive as
possible and highly organized. Record all observations of a separate sheet of paper, identifying
each observation as to what reactants were allowed to react.

You have been given six unknown solutions. You have also been given six known solution,
cyclohexanol, 1-propanol, 2-propanol, 1-butanol, t-butyl alcohol and 2-octanol. Each of the six
unknown solutions is one of the six know solutions. Devise a scheme, using the given test
reagents and deionized water to identify each of the unknown solutions.

Three common solutions have been given, antiseptic, antifreeze and the main ingredient in skin
lotions. Prove that these are all alcohols and classify each as 1, 2 or 3 alcohols.

Concluding Questions:
1. Draw the structure of each of the known solutions molecules.

2. Identify each of the unknown solutions:

1
2
3
4
5
6

3. What is the classification of each of the common solutions?

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4. What are the actual compounds in these common solutions? Draw their structures.

5. Which test reagent(s) should be used to differentiate between the following two alcohols?
Explain.
H H H OH H
H C C OH H C C C H
H H H H H

6. Vodka is 99.9% mixture water and ethanol. Why don’t these two compounds separate as oil
and water do?

7. Draw the structure of isopropyl alcohol. What is the IUPAC name for this compound?