Lab #2 (Plan and Design)

Date: 24/10/2021

Title: Distinguishing between different types of alcohols.

Problem Statement: Candice has 3 different types of alcohol with a molecular

formula C4H10O. She observed that only 2 out of 3 alcohols resulted in a colour
change from orange to green when warmed with acidified K2Cr2O7. Propose a
hypothesis for her observation and design an experiment to test your hypothesis.

Hypothesis: Sample A and B can be oxidized because they are primary and
secondary alcohols respectively, whereas, Sample C is a tertiary alcohol and is not
able to be oxidized.

Aim: To determine among samples A,B and C, which are primary, secondary and
tertiary alcohols.

Apparatus/Materials: measuring cylinder, droppers, 50°C water bath,

thermometer, tripod stand, white tile, Bunsen burner, test tube, test tube clamp, test
tube rack, stopwatch, Sample A, Sample B, Sample C, aqueous iodine, acidified
sodium hydroxide, acidified potassium dichromate.

Procedure:

Part #1 : Differentiating primary and secondary alcohols from tertiary alcohols

1. Add 5cm3 of Sample A to a test tube.

2. Add 2-3 drops of acidified potassium dichromate to test tube with Sample A
3. Gently warm sample in water bath and time using a stopwatch for 5 minutes.
4. Record and tabulate all observations and results
5. Repeat steps 1-4 for Samples B and C

Part #2: Differentiating between a primary and secondary alcohol

1. Add 5cm3 of Sample A to a test tube.

2. Add 2cm3 of sodium hydroxide and 1cm3 of aqueous iodine to test tube
3. Record and tabulate all results and observations
4. Repeats steps 1-3 for Samples B and C
Variables:

Controlled:

1. Volume of sample A,B and C used.

2. Volumes/Amounts of reagents added to samples A,B and C.
3. Temperature of water bath used for heating samples.

Manipulated:

1. Type of alcohol present in each sample.

Responding:

1. Colour changes when adding reagents.

Diagram:

Table of Results:

Expected Results:

If Samples A and B becomes oxidized and changes colour from orange to green
while Sample C does not become oxidized and remains the colour orange in part
#1 of the experiment, and upon addition of sodium hydroxide and aqueous iodine,
only sample B gives a yellow precipitate while samples A and C shows no change
in part #2 of the experiment, then hypothesis is true and is expected.

If Samples A and B do not become oxidized and remains the colour orange while
Sample C becomes oxidized and changes from orange to green in part #1 of the
experiment, and upon addition of sodium hydroxide and aqueous iodine, sample B
does not give a yellow precipitate while samples A and C shows a change in part
#2 of the experiment, then hypothesis is false and rejected.

Treatment of Results:

Alcohols are organic compound which contain at least one hydroxyl -OH group
bound to a saturated carbon atom. The general formula for an alcohol is CnH2n+1OH
and it can be classified into three groups depending on the position of the hydroxyl
-OH functional group. These three classes of alcohols include: Primary (1°),,
Secondary (2°) and Tertiary(3°). A primary alcohol is one in which the carbon
atom that carries the -OH group, is only attached to one alkyl group. A secondary
alcohol is one in which the carbon atom that carries the -OH group, is attached to
two alkyl groups while a Tertiary alcohol is one in which the carbon atom that
carries the -OH group, is attached to three alkyl groups.

The difference can be shown in the diagram below:

Primary alcohols and Secondary alcohols are known to have the ability to be
oxidized to form aldehydes/ketones whereas Tertiary alcohols cannot be oxidized
to form any carbonyl groups. This is because the tertiary carbon atom has three
single bonds to other carbon atoms and one single bond to the oxygen of the
hydroxyl-group. To form a carbonyl-group, you need a double bond. Carbon can
only form 4 bonds and the C---C bonds are relatively stable, so it can't form the
carbonyl-group.

In this experiment, two parts were involved: Part A and Part B. Part A of the
experiment was used to distinguish between Primary and Secondary alcohols by
testing all three samples; Sample A, Sample B and Sample C. The oxidizing agent,
acidified potassium dichromate H+(aq)/K2Cr2O7(aq) was used while the alcohol used
was butanol C4H10O. The primary alcohols present in either Samples A will appear
as isomers of butanol and can either be butan-1-ol (CH3CH2CH2CH2OH) or 2-
methylpropan-1-ol (CH2CH(CH3)CHOH). When exposed to the oxidizing agent H+
(aq)/K2Cr2O7(aq) , the primary alcohol will be only be oxidized to an aldehyde.

Therefore, if If the primary alcohol is butan-1-ol (CH3CH2CH2CH2OH) it will be

oxidized into the aldehyde, butanal and if primary alcohol is 2-methylpropan-1-ol
(CH2CH(CH3)CHOH) it will be oxidized into the aldehyde, 2-methylpropanal. In
this experiment, the conditions did not accommodate the further oxidation of
butanal to a carboxylic acid which would have accounted for colour change from
orange to green. This occurs when a stronger oxidizing agent is used, for example,
acidified potassium permanganate, and it is heated under reflux.

The oxidation of a primary alcohol using butan-1-ol is shown below using the
structural formula:
In sample B, the secondary alcohol will be in the form of the isomer, butan-2-ol
(CH3CHOHCH2CH3). When exposed to the oxidizing agent, H+(aq)/K2Cr2O7(aq), the
alcohol will be oxidized to form a ketone, butanone. When this alcohol is oxidized
this causes the reduction of the oxidizing agent H+(aq)/K2Cr2O7(aq), resulting in a
colour change from orange to green. This colour change is due to the reduction of
the orange dichromate ions (Cr2O7-(aq) ) to green chromium ions (Cr3+(aq)).

The oxidation of the secondary alcohol using butan-2-ol is shown using the
structural formula below:

In sample C, the tertiary alcohol will be in the form of the isomer, 2-methylpropan-
2-ol (CH3C(CH3OH)CH3). When exposed to the oxidizing agent, H+(aq)/K2Cr2O7(aq),
no colour change would be observed due to inability of tertiary alcohols to become
oxidized. Hence, the colour of the acidified potassium dichromate remains orange.

The structural formula of the tertiary alcohol 2-methylpropan-2-ol is shown below:

Part B of this experiment was used to distinguish between primary and secondary
alcohols, since they both become oxidized, by carrying out the Idoform test.
Secondary alcohols contains the group (CH3CHOH) while primary alcohols do not,
hence, with the addition of sodium hydroxide (NaOH(aq)) and aqueous iodine (I2(aq)),
they can be distinguished. In the presence of sodium hydroxide, this group is
oxidized by iodine to form a yellow precipitate which is commonly known as the
triiodomethane precipitate. Primary alcohols do not give a positive reaction to this
test and neither to tertiary alcohols as they do not have the ability to become
oxidized.
The equation for this Idoform test is shown below:

Precautions:

1. Label test tubes A, B and C, respectively to avoid confusion with each

sample.
2. Keep alcohol at a distance from open flames due to highly flammable nature.
3. Use a white tile when observing colour changes.
 4. Remove contaminants by carefully washing all apparatus before use.
5. Wear lab attire such as lab coats, goggles and gloves when handling
acidified substances.

Sources of Error:

1. Temperature of water bath may be difficult to maintain at same temperature

for all samples.
2. Colour may be subjective.

Assumptions:

1. All reagents were free from impurities.

2. There was a high enough concentration of alcohol for a reaction to occur.
3. Acidified substances were concentrated enough for a reaction to occur.