Kevin Ren D/CH 7/02/2017

ANALYZING ALCOHOLS
AIM
The aim of this report is to outline a procedure which will allow us to determine whether an
unknown liquid A is a primary, secondary or a tertiary alcohol.

EQUIPMENT
 Potassium dichromate (VI)
 Test tube
 Hot water bath
 Rubber bong
 Concentrated Sulfuric acid
 dropper

METHOD
1. Add 8 drops of liquid A (in excess) into a test tube using dropper
2. Add 5cm3 of potassium dichromate (VI) to the same test tube using dropper
3. Add 1cm3 of concentrated sulfuric acid to act as a catalyst for the experiment.
4. Put rubber bong over test tube
5. Shake to mix the solution
6. Put the test tube into a water bath for approximately five minutes.

This will determine whether liquid is a primary or secondary alcohol. Both primary and
secondary alcohols will make the dichromate oxidise, thus produce a colour change turning
the orange solution to green. However, with a tertiary alcohol a colour change will not occur,
so we can confirm liquid A is a tertiary alcohol if no colour change is obtained.
An equation for the reaction of a primary alcohol (example ethanol) is shown below. The
primary alcohol reacts to form aldehydes. We have made sure to add excess alcohol so that
no carboxylic acid is formed.
3CH3CH2OH + Cr2O72- + 8+  3CH3CHO + 2Cr3+ +7H2O

A general equation for primary alcohols would be:

RCH2OH + [O]  RCHO + H2O

The colour change occurs because the dichromate ion which was once orange turns into a
Cr3+ which is green.
A secondary alcohol oxidises to from ketones with the equation:
R1CH(OH)R2 + [O]  R1COR2 + H2O

This reaction also initiates the colour form orange to green.

Kevin Ren D/CH 7/02/2017

FURTHER EQUIPMENT USED

 Tollens reagent
 Fehling solution

TOLLENS REAGENT
There are two popular methods to testing between an aldehyde (oxidise primary alcohol) and
a ketone (oxidised secondary alcohol).
1. Put the oxidized liquid A into a test tube
2. Add Tollens reagent to the test tube
3. Put on tuber bong
4. Shake to mixture the solution
5. Put in hot water bath

If an aldehyde is present. It reduces the silver amine complex to metallic silver which forms a
‘silver mirror’ precipitate on the inside of the test tube. IF this occurs we can conclude that
liquid A is a primary alcohol. If no reaction occurs, it will be secondary alcohol. The silver
mirror occurs because of the silver formed due to the reaction in the following equation.

FEHLING’S SOLUTION
1. Put the oxidized liquid A into a test tube
2. Add Fehling’s solution to the test tube
3. Put on tuber bong
4. Shake to mixture the solution
5. Put in hot water bath

Fehling’s solution is a blue alkaline solution of copper(II) ions. If an aldehyde is present, the
solution turns brick-red colour. The aldehyde reduces copper(II) ions to form a precipitate of
coper(I)oxide. This is shown in the equation below:

RISK ASSESSMENT
 Sulfuric acid is corrosive to eyes and cause conjunctivitis and inflammation of the eyelid lining so we
will wear eye protection to protect ourselves.
 Make sure all equipment used is not chipped. Insuring that is not the case is because chipped test tube
can lead to cut and injuries.
 Avoid getting hot water onto skin. This can lead to burns and damage skin in both long and short term.
It can soften skin oils leading to moisture in skin easily escaping resulting in dry and itchy skin.
 Working with alcohols can be dangerous because they are flammable so there should not be anything
which can cause sparks or fire nearby eg lighters cigarettes.
Kevin Ren D/CH 7/02/2017

 Inhaling fumes of alcohol can be dangerous and can lead to irritating the respiratory system as well the
vapors may cause dizziness
 If alcohol is swallowed it can be very dangerous. Make sure to wash out with water and make sure not
to vomit as may alcohols become vapors easily and could lead to it staying around in the oesophagus
leading to further damage as well as vomiting being the cause of some illnesses such as Barrett’s
oesophagus. Also call a doctor.
 If alcohol gets in the eye wash out the eye with gently running water for up to 10mins.

SOURCES
 Barrett’s Oesophagus. Abnormal Lower Gullet; Causes [WWW Document], n.d. URL
http://patient.info/health/barretts-oesophagus-leaflet (accessed 2.15.17).
 Oxidation of aldehydes and ketones [WWW Document], n.d. URL
http://www.chemguide.co.uk/organicprops/carbonyls/oxidation.html (accessed 2.15.17).
 Student Safety Sheets - 66 Higher alcohols (propanols, butanols, pentanols) [WWW Document], n.d.
URL http://webcache.googleusercontent.com/search?q=cache:hyXwA3n-
ImEJ:www.cleapss.org.uk/attachments/article/0/SSS66.pdf%3FSecondary/Science/Student%2520Safe
ty%2520Sheets/+&cd=1&hl=en&ct=clnk&gl=uk (accessed 2.15.17).
 Are long, hot showers bad for your skin? [WWW Document], 2010. . HowStuffWorks. URL
http://health.howstuffworks.com/skin-care/cleansing/myths/hot-showers-bad.htm (accessed
2.15.17).