Oxidizing Primary, Secondary, and Tertiary Alcohols

Yasoda Subramanian

SCH 4U1

Teacher: Mr. Damude

Date Due: Wednesday, December 1, 2010

Purpose:

The purpose of this lab was to determine the differences in the reactions between primary,
secondary, and tertiary alcohols, and an oxidizing agent.

Materials:

 1 squirt of
- Ethanol
- 1 – Propanol
- 2 – Propanol
- 1 – Butanol
- 2 – Butanol
- 2 – Methyl – 2 – Propanol
 Distilled Water
 Spot plate
 Sulphuric Acid (H2SO4)
 Potassium Permanganate (KMnO4)
 Stop watch
 Safety glasses
 Paper towel

Procedure:

1. Wearing safety glasses, rinse the spot plate with distilled water, and using the tape.
2. In one of the spot plate ‘dips’ drop 2 drops of KMnO4, 1 drop of H2SO4 and 3 drops of one
of the alcohols.
3. Start the stop watch the instant the 3 squirt of an alcohol hits the spot plate.
4. Stop the stop watch when the solution turns orange/pink colour.
5. Note the time on the stop watch as part of your quantitative observations.
6. Repeat steps 2 – 5 for all the other alcohols.
7. When finished, cleanup work area, disposing of all wastes appropriately.

Observations:

Alcohol Time Taken to be Oxidized (Seconds)

Ethanol 00:03:00
1 - Propanol 00:02:00
1 - Butanol 00:23:56
2 - Butanol 00:01:28
2 - Propanol 00:05:28
2 - methyl - 2 - propanol No reaction
Analysis (Pg 74 # 1 – 4):

1.

2. a) Ethanol, 1 – Propanol, 1 – Butanol, 2 – Butanol, and 2 - Propanol all reacted with the
potassium permanganate because they are primary and secondary alcohols. When the
alcohols were added to 2 drops of KMnO4, 1 drop of H2SO4, they changed colour (orange-
ish) after a few seconds (some faster than others).

b) 2 - methyl - 2 - propanol did not react with potassium permanganate because it is a

tertiary alcohol. A tertiary alcohol cannot be oxidized. Carbon can form up to four binds,
but all possible bonding sites are occupied. C – H bonds can be broken by oxidizing
agent. On the carbon atom of a tertiary alcohol, however, there is no hydrogen atom
available to be removed. C – C bonds are too strong to be broken by an oxidizing agent.

3. 2 – Butanol reacted the most quickly, with 2 - methyl - 2 – propanol having no reaction
during the given time for the procedure. The tertiary alcohol was the slowest to oxidize,
while a secondary alcohol was the quickest to oxidize.
4.

Conclusion:

5. The secondary alcohol, 2 – Butanol reacted quickly.