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

Reduction Reactions in Organic Chemistry
End of Chapter Problems

1. 10.14 Provide the major organic product for each of the following reactions.

2. 10.15 Provide the organic reactant to complete each of the following reactions.

3. 10.16 Show how you could use a Grignard reagent and a C=O containing compound to make each of the following compounds.

4. 10.17 Show how to carry out the following transformation.

5. 10.18 Show how to carry out the following transformations. For each step in your synthesis, clearly show all reagents and reaction conditions.

6. 10.19 Show how you could use ethylene oxide (oxirane) and an alkyne to synthesize each of the alcohols shown below.

7. 10.20 Show how to carry out the following transformations.

8. 10.21 Muscalure is the sex attractant of the common housefly, it is cis-tricos-9-ene and its structure is shown below. Starting with any alkyne, devise a synthesis for this compound.

9. 10.22 Tertiary alcohols can be synthesized by the reaction of a Grignard reagent (RMgX) with an appropriate ketone as shown in the reaction below for the synthesis of 3-methyl-3-hexanol.

Utilizing a similar strategy as given in the example above, outline the synthesis of the same molecule, 3-methyl-3-hexanol, but utilizing a different Grignard reagent and ketone.

10. 10.23 Show how to carry out the following transformation. For each step in your synthesis, clearly show all reagents and reaction conditions.

11. 10.24 Show how to carry out the following transformations. For each step in your synthesis, clearly show all reagents and reaction conditions.