Oxidation of Alcohols

Research question: Which method (distillation and reflux) is more effective to complete the
process of oxidation of ethanol using potassium dichromate?
Objectives:
- Understand the oxidation of alcohols
- Learn about the different kinds of alcohols and their characteristics
- Analyze the different methods to complete the oxidation of alcohols
- Study the formation of aldehydes and ketones when the oxidation process is
finished
Hypothesis: Reflux process is more effective because is a closed circuit, avoiding the
substance to be lost in the environment. It is also more effective because it is emphasized
on oxidizing the ethanol, while distillation makes a separation and oxidation of the ethanol
in water.

Introduction:
Alcohols are a group of molecules characterized by the presence of one or more groups –
OH as a principal group. The structure of an alcohol resembles to the water structure, since
an alcohol proceeds from the substitution of one of the hydrogens by an alkyl group.
Alcohols can be classified in three different structures, primary alcohols, secondary
alcohols and tertiary alcohols.
Primary Alcohols
In primary alcohols the carbon atom that is attached to the –OH group is attached to
only one alkyl group.

Primary alcohols can be oxidized to either carboxylic acids or aldehydes, it depends on the
reaction conditions. When the oxidation results in a carboxylic acid, the alcohol is first
oxidized to an aldehyde and then it is oxidized to a carboxylic acid. An aldehyde is
obtained when an excess of alcohol is present and the aldehyde is removed to prevent a
further reaction, this refers to the fact that there is not enough oxidizing agent to pass to the
second stage. For example, if ethanol is used as primary alcohol, the result will be ethanal,
as shown in the equation below.
3+ ¿+7 H O¿
2

2−¿+8 H + ¿→3 C H CHO+ 2C r ¿

¿
3 C H 3 C H 2 OH +Cr O
3

For obtaining a carboxylic acid, a full oxidation is needed. An excess of oxidizing agent has
to be present to complete and the aldehyde formed is still in the mixture. The alcohol is
heated in a reflux with the excess of oxidizing agent and when the reaction is complete the
carboxylic acid is obtained. The full oxidation of ethanol is ethanoic acid, as shown in the
equation below.
3 +¿+ 11H 2 O ¿

3 C H 3 C H 2 OH +Cr O 2−¿+16 H →3 C H COOH +4 C r

3 ¿
7

Secondary Alcohols
In secondary alcohols the carbon atom that has the –OH group attached is joined to two
alkyl groups, that can be different or equal.

Secondary alcohols can only oxidize to ketones. For example, propanone is formed when
the secondary alcohol propan-2-ol with sodium or potassium dichromate (VI) solution
acidified with dilute sulfuric acid is heated, as shown below.
Tertiary alcohols
In tertiary alcohol the carbon atom that has the –OH group is joined to three alkyl groups,
that can be the combination of different or equal groups.

Tertiary alcohols cannot be oxidized because there is no

hydrogen attached to the carbon with the –OH group. If tertiary alcohols are compared with
primary and secondary alcohols, it can be identified that the oxidizing agent removes the
hydrogen the –OH group and a hydrogen from the carbon atom attached to the –OH group.

Materials:
- Ethylic alcohol
- Sulfuric acid
- Potassium Dichromate
- Universal support
- Liebig condenser
 - Container
- Condenser tube
- Distillation flasks
- Thermometer
- Bunsen Burner
- Water bath container
Distillation:
Method:
First, water has to be added in in a distillation flask. Then, the thermometer is placed in the
mouth of the flask. Next, 5ml of ethanol are added to the flask in the water and 5g of
potassium dichromate are also added, the mixture has to be stirred. After this, the flask has
to be placed on a Bunsen burner and the solution will be heated until its color change (Time
of the reaction required). When the color of the solution changes, the burner is turned off
and notes are taken of the changes in the solution (time, temperature, color, etc).

Reflux:
Method:
First, the water bath container has to be placed above the Bunsen burner. Then, the
distillation flask has to be located in the container and sit the Liebig condenser above the
distilled flask, sustained by the universal support. Next, 5ml of ethanol are added to the
flask and after doing this 5ml of potassium dichromate and sulfuric acid are added. After
this, the solution is heated (taking the time) until a change in the solution color is observed.
Finally, notes of the occurred in the process are
taken.
References:
Clark, J. (16 de Julio de 2015). Chemistry libretexts. Obtenido de
https://chem.libretexts.org/LibreTexts/Purdue/Purdue_Chem_26100%3A_Organic_Chemi
stry_I_(Wenthold)/Chapter_10%3A_Alcohols/10.1_Structure_and_Classification_of_Alcoh
ols

Clark, J. (30 de Septiembre de 2018). Organic Chemistry. Obtenido de

https://chem.libretexts.org/Textbook_Maps/Organic_Chemistry/Supplemental_Modules_
(Organic_Chemistry)/Alcohols/Reactivity_of_Alcohols/The_Oxidation_of_Alcohols

Fernández, G. (Mayo de 2015). Quimica Orgánica. Obtenido de

https://www.quimicaorganica.org/alcoholes/418-oxidacion-de-alcoholes.html

Lopez, J. C., Reyes, A., Barceló, M., & Teáhulos, I. (Mayo de 2013). Laboratorio de quimica
experimental. Obtenido de http://quimexequipo8.blogspot.com/2013/03/practica-16.html