1. Nomenclature Worksheet 4
Chem 350
Organic Chemistry II
Spring, 2014
3/2-5/15
Chapter 19
Nomenclature Worksheet 4
Model 1
Chem Act 19 Models 1 - 4
Carbonyls
C=O
not acidic
is acidic

2. Phenol - Quinone Redox
Edmond Frḗmy
Frḗmy’s salt (1845)

3. Biological Quinones
Hydroquinone is used as a developer for film. It reacts with light-sensitized AgBr grains, converting it to black Ag.
Coenzyme Q is an oxidizing agent found in the mitochondria of cells.

5. Carbonyls with and without Leaving Groups

6. Carbonyls C=O RCHO (R)(R’)C=O

7. Carbonyls IR

8. Carbonyls NMR
C8H10O IR 1750 cm-1

9. Select the correct IUPAC name for the following molecule.
2-ethyl-3-cyclopentenone
1-ethyl-5-cyclopenten-2-one
2-ethylcyclopent-2-en-1-one
1-ethyl-2-cyclopenten-5-one
2-ethyl-1-keto-2-cyclopentene

10. What is the product of the following reaction?1. 2. 3. 4. 1 2 3 4

11. Nucleophilic Addition to Carbonyls

12. Electrophilicity Aldehydes > Ketones

13. Two Mechanisms

14. Chem Act 23 Model 1

15. Chem Act 23 Model 2 Hydration

18. Chem Act 23 Model 4 Cyanation

19. From one cyanohydrin to another !

20. What would be the expected outcome if one equivalent of a Grignard reagent were reacted with the molecule shown below?
Nucleophilic addition exclusively at carbonyl A
Nucleophilic addition exclusively at carbonyl B
Equal addition at both carbonyls
Greater percentage of addition at carbonyl A
Greater percentage of addition at carbonyl B

21. Rank the following carbonyl compounds from most to least reactive when treated with a nucleophile.
A > C > B > A
C > B > A > D
A > B > C > D
A > C > B > D
C > B > D > A
All are equally reactive

22. The following reaction will occur as shown.
True
False
Sometimes
Not sure

23. What sequence of reagents will accomplish the following transformation?2. 3. 4. 5. 1. 1 2 3 4 5

24. Which sequence will produce the following transformation?1. 2. 3.
Both (1) and (2) are possible 4.
Both (2) and (3) are possible 5. 1 2 3 4 5

25. Chem 350 Organic Chemistry II Spring, 2015 Chapter 19
Organic Chemistry II
Spring, 2015
Chapter 19
>C=O  >C(OH)2 , >C(OH)(OR) , >C(OR)2
C=O  C=N
C=O  C=C
Conjugate Addition on C=C-C=O
First Review

26. Which of the following represents a hydrate?1. 2. 3. 4. 5. 1 2 3 4 5

27. Which of the following represents a hemiacetal?1. 2. 3. 4. 5. 1 2 3 4 5

28. Which of the following represents an acetal?1. 2. 3. 4. 5. 1 2 3 4 5

29. Select the starting material used to make the following acetal.1. 2. 3. 4. 5. 1 2 3 4 5

31. Enamines Worksheet together

33. What is the final product of this reaction ?2. 1. 3. 4. 5. 1 2 3 4 5

34. What is the correct functional group assignment for each of the following nitrogen-containing compounds?
A = imine, B = amine, C = enamine, D = oxime
A = oxime, B = amine, C = enamine, D = imine
A = oxime, B = amine, C = imine, D = enamine
A = oxime, B = enamine, C = oxime, D = amine
A = oxime, B = imine, C = amine, D = enamine

35. Chem Act 23, CTQ 29, page 415

38. Which combination of reagents will yield the following compound?1. 2. 3.
Both (1) and (2) 4.
Both (2) and (3) 5. 1 2 3 4 5

39. How can we synthesize these ?

41. In an α, β unsaturated carbonyl group CBETA=CALPHA-C=O the polarity of the alpha and beta carbons are:
Positive and Positive
Negative and Negative
Positive and Negative
Negative and Positive
Both have no polarity

42. Conjugate (“1,4”) Addition

43. Do Chem Activity handout “23 D”

44. 1,2 (direct) vs. 1,4 (conjugate)

46. 1,2 (direct) vs. 1,4 (conjugate)X

49. Conjugate (“1,4”) Addition