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

Addition Reactions Involving Carbonyls and Nitriles
End of Chapter Problems

1. 9.16 Show how to carry out the following transformations. For each step in your synthesis, clearly show all reagents and reaction conditions.Image

2. 9.17 Propose a reasonable mechanism for the hydrolysis of the acetal shown below (hint: the first step in the mechanism is given).Image

3. 9.18 Show how to carry out the following transformation, clearly show all reagents and steps in your reaction sequence if your synthesis is a multistep synthesis (hint: you may have to protect one of these functional groups while carrying out a reaction on the other functional group).Image

4. 9.19 Three different alkenes (A, B, and C) yield 2-methylbutane when they are hydrogenated in the presence of a metal catalyst. Give the structures and IUPAC names of the three compounds.

5. 9.20 9.20 Show how to accomplish the following transformation, clearly show all reagents and reaction conditions necessary to carry out each step in your synthesis (hint: consider using an appropriate hydration reaction followed by an oxidation reaction to form the ketone).Image

6. 9.21 Determine which of each of the following pairs of ketones is more reactive toward hydration?Image

7. 9.22 Propose a reasonable mechanism for the hydrolysis of the nitrile shown below to form an amide (hint: the first step in the mechanism is shown).Image

8. 9.23 Propose reasonable mechanisms for the following reaction (hint: the first steps for each mechanism are shown).Image

9. 9.24 Show how to carry out the following transformations. For the steps in your syntheses, clearly show all reagents and reaction conditions (hint: note that the products of these reactions have more carbons than the reactants, additional carbons are shown in red; think of adding extra carbons via a Wittig reaction to form an alkene, then an addition reaction, shown in green).Image

10. 9.25 Show how to accomplish the following transformations (synthesis). All reagents, reaction conditions, and appropriate solvents must be clearly shown.ImageImage

11. 9.26 The cyclopropane group is typically found in insecticides. Molecule 2, shown below, is a long-lasting inhibitor for some enzymes. On the arrow, give appropriate reagents that can be used to carry out the transformation shown.Image

12. 9.27 Ketones can be converted to 1,3-dithiolanes as shown in the reaction below. Using arrow-pushing formulism to indicate electron movement, propose a reasonable mechanism for the reaction shown below, which is carried out in an acidic medium (hint: the first step in the mechanism is given, the next step involves the nucleophilic sulfur adding to the electrophilic carbon).Image

13. 9.28 Provide structures for the lettered compounds for each of the reaction scheme shown below.Image

14. 9.29 Using arrow-pushing formulism to indicate electron movement, provide a reasonable mechanism for the following reaction; hint the first step is shown.Image

15. 9.30 Using arrow-pushing formulism to indicate electron movement, provide a reasonable mechanism for the following reaction.Image

16. 9.31 Show how to carry out the following transformations. For the steps in your syntheses, clearly show all reagents and reaction conditions.Image