NAME: Brandon Ramkissoon

DATE: 6th April 2017

TITLE: Planning and Design - Alcohols
PROBLEM
STATEMENT: Karla was given three different alcohols, each with a molecular formula of C4H10O.
She observed that only two out of the three alcohols resulted in a colour change from orange to
green when warmed with acidified potassium dichromate. Suggest a hypothesis for this.

HYPOTHESIS: The alcohol samples were primary, secondary and tertiary which can be tested by
determining the products formed when oxidized.

AIM: To distinguish between the samples, which one is primary, secondary and tertiary.

THEORY: The product obtained when oxidizing an alcohol depends on the type of alcohol and the
power of the oxidizing agent. Primary alcohols are readily oxidized to aldehydes on heating but in
the presence of excess oxidizing agent the reaction proceeds further producing a carboxylic acid.
Secondary alcohols are oxidized to the corresponding keytones while tertiary alcohols are not
readily oxidized under these conditions.
The products formed can then be distinguished with further tests. Mild oxidizing agents such as
Tollens and Fehlings reagent can oxidize aldehydes but not ketones. Tollens reagent consists of a
solution of silver nitrate in excess ammonia solution. It forms a silver mirror on the wall of the test
tube with an aldehyde. However, Fehlings reagent gives a brown precipitate of copper(I) oxide
with the aldehyde. Fehlings reagent consists of a solution of Copper(II) sulphate added to Rochelle
salt in excess sodium hydroxide.

APPARATUS: 4 droppers, (7) test tubes, test tube holder, test tube rack, bunsen burner, 250cm3
beaker, tripod stand, wire gauze.

MATERIALS: Samples of alcohols, acidified potassium dichromate, Fehlings reagent, NH3 and
AgNO3, distilled water, potassium permanganate
DIAGRAM:
METHOD A:
1. Set up apparatus as shown in diagram above.
2. Label each alcohol sample, A, B and C respectively.
3. Add 2cm3 of each sample to a test tube followed by a few drops of potassium dichromate and
placed in the water bath.
4. Record observations.
METHOD B: To be done on sample that were oxidized from method A.
1. Add a few drops of potassium permanganate to 2 test tubes then add 2cm3 of each sample in a
test tube.
2. Add a few 2cm3 of AgNO3 to a test tube followed by drops of ammonia. Shake until the
precipitate formed dissolve and then add 2cm3 of one of the samples and heat gently.
3. To another test tube, add Fehlings reagent, followed by 2cm3 of the same sample. Heat
gently and record any observations.
4. Repeat steps 2 and 3 with the other sample.

VARIABLES: Manipulated: Reagent added to samples.

Constant: Volume of samples used.
Responding: Colour of solutions and Precipitate.

EXPECTED RESULTS:
Table 1.1: Observations with Acidified Potassium Permanganate

Sample Colour Changes

Table 1.2: Observations with test reagents.

Sample Tollens Reagent Fehlings Reagent

TREATMENT OF RESULTS:
For reaction with Acidified potassium dichromate:
Primary alcohols are oxidized to the aldehyde:
[O]
C4H10O(aq) C3H7CHO(aq)
H+/CrO2O72-

Secondary alcohols are oxidized to the keytone:

[O]
C4H10O(aq) C2H5CH53CO(aq)
H+/CrO2O7 2-

Both reaction changes from orange to green.

Whereas, the tertiary alcohol does not oxidize under these conditions and results in no colour
changes.
Potassium Permanganate was then added to these same samples for a purple to colourless colour
change.
This colourless solution is then reacted with the different reagents so that the precipitate is seen.

With the Tollens reagent of silver nitrate in excess ammonia solution, aldehydes reduce the silver
ion to silver which is precipitated and forms a mirror effect on the bottom on the test tube.
This is indicated by the equation:
RCHO(l) + 2Ag+(aq) + H2O(l) RCOOH(aq) + 2Ag(s) + 2 H+(aq)

For clarification, Fehlings test is carried out on the samples. When reacted, aliphatic aldehydes
reduce copper(II) ions to reddish brown copper oxide which is precipitated.
This is indicated by the Equation:
RCHO(l) + 2Cu2+(aq) + H2O(l) RCOONa(aq) + Cu2O(s) + H+(aq)
PRECAUTIONS: Do not let any reagents get onto skin.

ASSUMPTIONS: When carrying out varying tests, the reagents only reacted with the desired
compound in solution.

LIMITATIONS: Compounds in the samples when oxidized inhibit the reaction of some tests or
produce different precipitates. Example, when an alcohol sample is oxidized using
potassium permanganate, and Tollens reagent is added, this can react with a
by-product of the oxidation reaction to produce another precipitate.