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Oxidizing Alcohols Lab

SCH4U1 Mr. Wrigley Date: March 28/13
By: Aaron Lau

Question: How do primary, secondary, and tertiary alcohols react with an oxidizing agent? Prediction: Refer to prediction sheet attached. Materials: Refer to lab handout included. Procedure: Refer to lab handout included.

OBSERVATIONS Before Substances H2SO4(aq) H2O(l) KMnO4 butan-1-ol propan-2-ol 2-methylpropan-2-ol Qualitative transparent, colorless, liquid, odorless, aqueous transparent, colorless, liquid, odorless, distilled opaque, dark purple, liquid, bitter unpleasant smell colorless, potent odor, liquid, transparent potent odor, transparent, colorless, liquid colorless, odorless, liquid, transparent Quantitative 1.0mol/L, 2mL in each test tube 3mL used in control test tube 0.01mol/L, 3mL in each test tube, 3mL used in single test tube 3mL used in single test tube 3mL used in single test tube

After Substances Control Test Tube Test tube 1: propan-2-ol added Test tube 2: butan-1-ol added Qualitative opaque, light purple liquid Brown, opaque liquid, translucent liquid also formed. translucent oil substance formed a top layer, opaque brown liquid formed on bottom layer, brown solid formed, suspended in brown liquid opaque, light purple liquid Quantitative 8mL total: 3mL KMnO4, 2mL H2SO4(aq), 3mL water 8mL total: 3mL KMnO4, 2mL H2SO4(aq), 3mL propan-2-ol 8mL total: 3mL KMnO4, 2mL H2SO4(aq), 3mL butan-1-ol

Test tube 3: 2-methylpropan-2-ol added

8mL total: 3mL KMnO4, 2mL H2SO4(aq), 3mL 2-methylpropan-2-ol

Analysis 1. Draw the structure of each alcohol you used. Label each alcohol as primary, secondary, or tertiary.

propan-2-ol secondary alcohol

butan-1-ol primary alcohol

2-methylpropan-2-ol tertiary alcohol

2. a) Which alcohol(s) reacted with the potassium permanganate? How do you know? Propan-2-ol and butan-1-ol reacted with the potassium permanganate due to several indicators: both alcohols when mixed with the potassium permanganate caused it to turn from an opaque purple liquid to an opaque brown liquid. A brown precipitate was formed when butan-1-ol was mixed into its respective test tube. b) Which alcohol(s) did not react with the potassium permanganate? Explain your observations. 2-methylpropan-2-ol did not react with the potassium permanganate. This is shown by the control test tube and its contents. The control test tube contains an opaque, purple liquid which consists of 3mL KMnO4, 2mL H2SO4(aq), 3mL water. The compared test tube contains the same except 3mL of 2-methylpropan-2-ol instead of water. After an extended period of time the compared test tube showed no change. It had an appearance exactly the same as the control test tube: an opaque purple liquid. 3. Which alcohol(s) reacted the most quickly? which reacted slowly? make a general statement that summarizes your observations. Butan-1-ol reacted the most quickly. Propan-2-ol reacted more slowly. This concludes that primary alcohols oxidize faster than secondary alcohols.

Conclusions 4. Which alcohol reacted the fastest: primary, secondary, or tertiary? The primary alcohol, butan-1-ol, reacted the fastest compared to the others. 5. Were there any sources of experimental error? what could you improve if you did this investigation again? There were sources of experimental error: I assumed the propan-2-ol was finished reacting when it was still going through oxidation. Also, I may have put an extra .5mL water in the control test tube. If I could do this investigation again, I would spend an longer, set amount of time watching the contents of each test tube react ensuring the proper observations are recorded.