Organic Chemistry Laboratory I - Chem 341

Quiz 6d

1. Label the following reaction as an oxidation, a reduction, or neither. (2 Pts)

2. Consider the oxidation of cyclododecanol and answer the following question: Why was glacial acetic acid used in the reaction? (1 pt)

Glacial acetic acid protonates the bleach (NaOCl)

HOCl is the real oxodizing species.

3. What was the purpose of the starch iodide test last week? (1 pt)

Starch/Iodine test was performed to determine whether there is an excess of oxidizing agent present in the reaction mixture. If we did not have excess reagent, then it is possible that some of the starting alcohol was not converted to the ketone. This would reduce the yield and complicate the purification.

A positive test turns the paper black and indicates excess bleach.

4. What region of the infrared spectrum (4000 – 600 cm^-1) would a carbonyl bond vibration show up in? (2 pts)

1800 - 1650 , most are around 1700

5. What solvent is most appropriate for cleaning an IR salt plate? (2 pts)

Any solvent that would not absorb atmospheric water will be suitable for cleaning a salt plate. The most commonly used is Methylene chloride, also known as Dichloromethane or CH₂Cl₂

6. Draw the structure of the major organic product. (2 pts)