Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Oxidation Reactions in Organic Chemistry
End of Chapter Problems

1. 11.19 Write balanced equations to show the combustion (oxidation) of each of the following alkanes to yield carbon dioxide and water.

2. 11.20 Complete the following reactions by supplying the missing reactant or major organic product.

3. 11.21 Complete the reactions shown below, by giving the structures of the major organic products.

4. 11.22 Give the oxidized organic product that results from the reaction of each of the following with PCC.

5. 11.23 Give the oxidized organic product for each of the reactions shown below.

6. 11.24 Give the alcohol and an appropriate oxidizing agent for the synthesis of the following aldehydes and ketones.

7. 11.25 Separate ozonolysis [O3 followed by (CH₃)₂S] of four (4) different compounds, A, B, C, and D, was carried out. The products obtained upon ozonolysis of each compound are shown below. Give the structures of the lettered starting compounds.

8. 11.26 East Indian sandalwood oil contains a hydrocarbon given the name santene (C₉H₁₄). Ozonolysis of santene gives compound X, as shown below. The same product was also obtained after the reaction of santene with KMnO₄ at elevated temperatures. What is the structure of santene?

9. 11.27 Ambuic acid, which has been isolated from a fungus that is associated with some forest plants, has been shown to have anti-inflammatory action, its structure is shown below. Give the product of the reaction of ambuic acid under acid hydrolysis, include stereochemistry where appropriate.

10. 11.28 Carissone, an extract from asteraceae, can be synthesized from the starting compound shown below. Show how to carry out the following transformation (hint: consider using an oxidation reaction and a reduction reaction; also, don’t forget the use of protecting groups).

11. 11.29 An unknown compound, W (C₇H₁₄), reacts readily with bromine in CCl₄ resulting in a colorless solution (C₇H₁₄Br₂). When W reacts with BH₃, followed by H₂O₂ in the presence of NaOH, a new compound, X (C₇H₁₆O) results, which when treated with KMnO₄ gives a carboxylic acid, Y (C₇H₁₄O₂). When W was subjected to ozonolysis, followed by the reaction with Me₂S, compound Z (C₆H₁₂O) is formed along with formaldehyde. It was shown that the oxidation of 3-hexanol using KMnO₄ also gave compound Z. What are the structures of W, X, Y, and Z?

12. 11.30 One of the constituents of turpentine is α-pinene, formula C₁₀H₁₆. Based on the reaction scheme shown below, give the structures of the lettered compounds.

13. 11.31 Show how to carry out the following transformations, include solvents and reaction conditions where appropriate.

14. 11.32 An unknown compound decolorizes bromine in carbon tetrachloride, and it undergoes catalytic reduction using hydrogen in the presence of a catalyst to give decalin. When the same unknown compound is treated with potassium permanganate at elevated temperature, it gives cyclohexane-1,2-dicarboxylic acid and oxalic acid (which was further oxidized, but not shown in reaction scheme below). Propose a structure for the unknown compound.

15. 11.33 An unknown compound, A, reacts with an excess of hydrogen in the presence of platinum as a catalyst to give compound B. When A is subjected to ozonolysis, the products C, D, and E are formed. What is the structure of the unknown alkene, A?