TOPIC: 19

TOPIC: 18. Aldehydes / Ketones

SUBTOPIC: 187. Aldol Reactions

1. Which carbonyl compound forms the most enol at equilibrium?

A. acetic acid

B. acetone

C. methyl acetate

D. acetamide

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2. Which carbonyl compound forms the most aldol at equilibrium?

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3. Which halogenation reagent reacts the fastest in the acid-catalyzed reaction?

A. Cl₂

B. Br₂

C. I₂

D. all the same

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4. Which halogenation reagent reacts the fastest in the base-promoted reaction?

A. Cl₂

B. Br₂

C. I₂

D. all the same

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5. Give the major product of the following reaction.

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6. Give the major product(s) of the following reaction.

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7. Give the major product of the following reaction.

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8. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products.

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9. Give a specific example of the interconversion of two tautomers by writing an equation. Use no generic R, X or Y groups in your answer.

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10. Give a specific example of the formation of an α,β-unsaturated enone from a ketone by writing an equation. Use no generic R, X or Y groups in your answer.

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11. Write the complete mechanism of the following reaction. Show all intermediates, electron-pushing arrows and formal charges.

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12. Give a specific example of an aldol condensation. Show starting material, reagents and products.

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13. Draw the structure of an enolate.

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14. Give the major product(s) of the following reaction.

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15. Give the major product(s) of the following reaction.

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16. Circle all protons in cyclohexenone that can be exchanged for deuterium with ⁻OD/D₂O.

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17. Draw the structure of an aldol.

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18. Write the complete mechanism of the following reaction. Show all intermediates, electron-pushing arrows and formal charges.

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19. Which compound that will not protonate lithium diisopropylamide (LDA).

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20. Which compound cannot be prepared in pure form by an aldol reaction?

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21. Show how you would accomplish the following synthetic transformation. Give all reagents and isolated products.

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22. Write the product(s) of the following reaction.

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23. Write two resonance structures for the product of the following reaction.

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24. Write the product(s) of the following reaction.

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25. Write the reagent(s) over the arrow. Number them if they cannot be mixed.

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26. Draw the two enols of the following ketone.

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27. Give the major product of the following reaction.

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28. Show how you would accomplish the following synthesis. Show all reagents over the arrow and intermediate isolated compounds.

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29. Which is the most acidic carbonyl compound? Which is the least acidic?

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30. Give the major product of the following reaction.

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31. Give the major product of the following reaction.

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32. Write the two best resonance structures of the product of the following reaction.

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33. Give the major product(s) of the following reaction.

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34. Write three resonance structures for the anion formed.

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35. Give the major product of the following reaction.

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36. Write the complete mechanism of the following reaction. Show all intermediates, electron-pushing arrows and formal charges.

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