CHM-236  Organic Chemistry II


Course Description:    Study of chemistry of carbon-containing compounds continued.  Structural determination and additional reaction mechanisms and modern methods of synthesis emphasized.
Prerequisites:    CHM235 and CHM235LL


Course Materials: 


Announcements
 

Here are some problem sets to get you started.

 

Here is quiz #5.  Print it out, complete it, and turn it in on or before Tuesday, November 24th.

Let me know right away if you encounter any printing or downloading problems.

 

I’ve also included relevant problems from the McMurry text (you’ll have to scroll down to see those.)

 

Problem Sets (from Smith text)

Chapter 16

     Conjugation:  1, 2, 13, 14, 28, 29, 39

     Resonance:  3, 6, 7, 8, 9, 11, 12, 30, 31, 32, 33, 34

     Diels-Alder reaction:  10, 18, 19, 20, 21, 22, 23, 24, 36, 37, 38, 46, 47, 48, 49, 50, 55, 56

     Addition reactions:  15, 17, 40

     Mechanisms:  16, 35, 41, 42, 43, 44, 45

     UV/visisble spectroscopy:  26, 27, 60

     NMR spectroscopy:  58

Chapter 17

     Resonance:  1, 12, 38

     Structure:  2, 24

     Nomenclature:  3, 4, 5, 25, 26

     Aromaticity:  8, 10, 11, 13, 14, 15, 16, 17, 18, 19, 20, 53

     Huckel rule:  21, 22, 27, 28, 29, 30

     Other problems:  31, 33, 34, 24, 25

     Mechanisms:  36, 48, 49, 50, 51

     Resonance:  38, 39

     Spectroscopy:  6

Chapter 18

     Reactivity:  1, 13, 14, 17, 18

     Mechanisms:  2, 3, 4, 7, 9, 11, 19, 45, 48, 49

     Reactions:  5, 6, 8, 10, 35, 36

     Disubstitution:  15, 16, 21, 22, 32, 33, 34

     Spectroscopy:  60, 61, 62, 63

     Substituents:  12, 20, 23, 41, 42, 43, 44, 46

     Syntheses:  24, 37, 40, 54, 55, 56, 57

     Side-chain reactions:  25, 26, 27, 28, 38

     More syntheses:  29, 30, 31, 39

Chapter 12

     Reduction vs. oxidation: 1

     Reductions:  2, 6, 10, 11, 12, 13, 14, 15, 32, 34, 36

     Oxidations:  16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 29, 30, 41, 45, 56, 47, 48, 49, 50, 51, 52

     Reactions:  31, 37, 38, 39, 40, 42, 43, 44

     Sharpless epoxidation:  53, 54, 55

     Syntheses:  56, 57, 58, 59, 60, 61, 62, 63

     Mechanisms:  64, 66

Chapter 15

     Types of radicals:  1, 2, 35, 36, 37, 38

     Halogenation:  3, 4, 5, 11, 12, 17, 18, 39, 40, 41, 42, 43

     Syntheses:  13, 15, 16, 44, 59, 60, 61

     Mechanisms:  19, 27, 29, 34, 45, 55, 58, 64, 68

     NBS:  19, 20, 21, 22, 23, 24, 26, 46, 47, 53

     HBr addition:  28, 30

     Polymers:  33, 66, 67

     Reactions:  48, 49, 50, 51, 52

     Spectroscopy:  69, 70

Chapter 19

     Nomenclature:  1, 2, 3, 4, 5, 28, 29, 30, 31

     Physical Properties:  6

     Other problems:  9, 23

     Preparation:  10, 11, 32, 33

     Acidity:  12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 47, 48, 49, 50

     Spectroscopy:  7, 8, 51, 52, 53, 54, 55

     Amino acids:  24, 25, 56

Chapter 20

     Structure:  1

     Types of reactions:  2, 3

     Reduction:  4, 5, 6, 7, 8, 9, 11, 12, 13, 14, 47

     Mechanisms:  10, 53, 54

     Oxidation:  15, 16, 46

     Organometallics:  17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33, 40, 41, 48

     Protecting groups:  25

     Synthesis:  36, 50, 51, 55, 56, 57, 62, 63, 64, 65

     Reactions:  37, 38, 39, 44, 45

     Stereochemistry:  49

     Spectroscopy:  67, 68, 69, 72

     Unsaturated carbonyls:  34, 35

Chapter 21

     Reactivity:  1, 2

     Nomenclature:  3, 4, 5, 6, 43, 44, 45

     Preparation:  11, 12

     Addition reactions:  13, 14, 15

     Imines and enamines:  23, 24, 25, 26, 27, 28, 62

     Hydrates and acetals:  31, 32, 33, 35, 36, 37, 63

     Reactions:  46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 59

     Spectroscopy:  10, 54, 83, 84

     Mechanisms:  74, 75, 76

     Wittig reaction:  17, 18, 20, 21, 22

     Syntheses:  61, 64, 65, 66, 67, 68, 72

Chapter 22

     Structure:  1, 2, 6, 9

     Nomenclature:  4, 5, 42, 43

     Reactions:  10, 11, 12, 13, 14, 15, 18, 44, 45, 46

     Spectroscopy:  8, 80, 81, 82, 83

     More reactions:  16, 19, 20, 22, 25, 26, 28, 33, 34, 47, 48, 49, 50, 51, 53, 54, 55, 57, 76, 77

     Mechanisms:  17, 21, 23, 29, 30, 58, 59, 60, 61, 64

     Syntheses:  27, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75

Chapter 23

     Enolates:  1, 2, 6, 7, 8, 9, 11, 29, 30, 31, 32, 34, 35

     Mechanisms:  5, 10, 12, 37, 40, 51, 53, 54

     Halogenation:  13, 15, 39

     Alkylation:  16, 17, 18, 19

     Malonic/acetoacetic ester syntheses:  20, 21, 2, 23, 24, 25, 26, 41, 42, 43, 45, 46

     Spectroscopy:  33, 62

     Reactions:  47, 48, 49, 50

     Syntheses:  56, 57, 58

Chapter 24

     Aldol:  1, 2, 4, 6, 7, 8, 9, 10, 12, 13, 26, 27, 28, 29, 30, 31

     Claisen:  15, 16, 17, 18, 19, 20, 21, 32, 33, 34, 35, 37

    

 

Problem Sets (from McMurry text, Fall 2008)

Reduction/Oxidation Reactions:

     Chapter 7:  13, 14, 15, 16, 20, 23a, 23d, 23e, 24a, 24b, 25a, 25b, 26a, 28, 29, 30, 31, 32, 33, 38, 40b, 40c, 43c, 44, 45

     Chapter 8:  8, 9, 12, 15a, 22, 23, 24c, 25a-b, 25f, 26d, 28, 29b, 29d, 30, 31, 38a-b, 42, 45

     Chapter 9:  61, 62

     Chapter 10:  13, 35

     Chapter 17:  7, 8, 14, 15, 35, 36, 40a, 57a, 57d

     Chapter 18:  15, 40, 41, 52a, 52d

     Chapter 19:  3a, 32a

     Chapter 20:  26a, 26e, 49e

 

Radical Reactions:

     Chapter 5:  2, 3, 17, 34, 37

     Chapter 7:  17, 18

     Chapter 9:  78

     Chapter 10:  3, 4, 5, 6, 7, 19, 20, 21, 23c, 24, 28, 29, 30, 31

     Chapter 16:  21, 73d


Chapter 13 (Review)
    Carbon NMR:  6, 7, 8, 25, 32, 55
    H1 NMR (types of H):  14, 15, 27, 31, 37
    H1 NMR (shifts):  16, 17, 39
    H1 NMR (signal size):  18
    H1 NMR (splitting):  19, 20, 24, 40, 41
    Structure elucidation:  21, 43, 44, 49, 50, 51, 52, 53, 56, 57


Chapter 14

    Diene electrophilic additions:  2, 3, 4, 17, 22, 27

    Diels-Alder reaction:  7, 8, 9, 10, 18, 19, 28, 33, 34, 36, 40, 44

    UV-visible spectroscopy:  16, 20, 23, 24, 31, 32, 46, 48, 49

 

Chapter 15

     Nomenclature:  1, 2, 3, 13, 18, 19, 20, 21, 22

     Resonance:  6, 11, 16, 17, 25, 26, 33, 36, 37, 39

     Aromaticity:  4, 5, 7, 8, 9, 10, 12, 31, 34, 38, 41, 47

     Spectroscopy:  14, 15, 42, 43, 44, 45, 46

     Reactions:  30, 35, 48, 49

 

Chapter 16

     Halogenation:  1

     Nitration and sulfonation:  2, 3

     Alkylation and acylation:  4, 5, 6

     Substituent effects:  7, 8, 9, 10, 11, 12, 13, 14, 25, 28

     Trisubstitution:  15, 16

     Side chain reactions:  19

     Syntheses:  21, 22, 23, 24, 26,50, 51, 52, 53, 54, , 69, 73

     Structure:  26

     Reactivity:  29, 30, 34, 43

     Orientation effects:  31, 32, 33, 40, 41, 42, 44

     Reactions:  35, 36, 47, 48

     Mechanisms:  37, 45, 49, 57, 59, 64, 65, 70, 74, 75

 

Chapter 17

     Nomenclature:  1, 2, 21, 26, 27, 29

     Physical properties:  3

     Acidity:  4, 5, 44

     Preparation:  6, 7, 8, 9, 10, 11, 25, 35, 37, 46, 47

     Reactions:  12, 24, 28, 33, 39

     Mechanisms:  34, 38, 45, 48, 39, 53

     Other reactions:  13, 14, 15, 16, 22, 23, 25, 30, 41, 43, 50

     Syntheses:  17, 31, 32, 36, 40, 42, 49, 52, 57

     Spectroscopy:  19, 20, 58, 59, 60, 61, 62, 63, 64, 65, 66

     More reactions:  67, 68

 

Chapter 18

     Nomenclature:  1, 17, 20, 24, 25

     Preparation of ethers:  2, 3, 4, 5, 6

     Ether reactions:  7, 8, 9, 26, 27, 31

     Epoxides:  11, 12, 13, 14, 15, 21, 22, 23

     Spectroscopy:  19, 53, 54, 56

     Syntheses:  28, 30, 32, 52

     Mechanisms:  33, 34, 35, 36, 37, 40, 41, 43

     Reactions:  29

 

Chapter 19

     Nomenclature:  1, 2, 28, 29, 30

     Preparation:  3, 4, 25

     Reactions:  5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 19, 20

     Spectroscopy:  21, 22, 24, 59, 60, 61, 62, 63, 64, 66, 67, 68

     Structure:  31

     More reactions:  32, 34, 41, 48

     Syntheses:  33, 36, 39, 40, 45, 46, 47, 52

     Mechanisms:  38, 44

 

Chapter 20

     Nomenclature:  1, 2, 16, 20, 21, 22

     Acidity:  3, 5, 6, 8, 17, 19, 23, 24, 32, 45, 47

     Preparation:  9, 18, 26

     Syntheses:  10, 11, 12, 13, 25, 27, 28, 34, 35, 36, 37, 38, 39, 40, 42, 46, 48

     Mechanisms:  41, 50

     Spectroscopy:  14, 15, 51, 52, 53, 54, 55, 56

     Reactions:  33, 43, 49

 

Chapter 21

     Nomenclature:  1, 2, 28, 32, 33, 34

     Mechanisms:  3, 7, 12, 15, 17, 30, 46, 47, 57, 58

     Reactivity:  4, 5, 31

     Reactions:  6, 9, 18, 19, 20, 36, 37, 38, 39, 40

     Syntheses:  8, 10, 11, 13, 14, 21, 22, 29, 35, 41, 50, 52, 53, 54, 55

     Spectroscopy:  26, 27, 64, 65, 66

 

Chapter 22

     Enols:  1, 2, 3

     Reactions:  4, 5, 6, 24

     Acidity:  7, 8, 19, 20, 21, 22, 23, 33

     Malonic esters:  11, 12, 13, 26

     Acetoacetic ester:  14, 15, 27, 28

     Alkylation:  17

     Syntheses:  18, 29, 37, 44

     Mechanisms:  25, 31, 32, 34, 35, 36, 38, 39, 40, 41

 

Chapter 23

     Aldol condensation:  1, 2, 3, 4, 10, 23, 25, 27, 29, 31, 35

     Syntheses:  7, 8, 28, 45, 46, 47, 48

     Claisen condensation:  11, 12, 13, 14, 15, 38, 39

     Michael reaction:  16, 17, 42, 43

     Stork-enamine:  19, 20, 51

     Robinson:  21, 22

     Mechanisms:  30, 32, 34, 50, 53

     Reactions:  37, 57

 

Chapter 24

     Nomenclature:  1, 2, 21, 25, 26, 27, 28

     Basicity:  4, 5, 6, 22, 24, 41, 42

     Synthesis:  7, 9, 10, 11, 17, 18, 31, 32, 33, 34, 35, 36, 45, 49

     Reactions:  14, 15, 29, 30, 37, 38, 39, 54

     Spectroscopy:  20, 66, 67, 68

     Mechanisms:  48, 70

    

 Here is the link to the problem sets for CHM 235 (Spring 2008).

Examples of NMR spectra

Examples of UV spectra

   

 

The following book may be a helpful resource as you prepare for your final exam:

    Preparing for Your ACS Examination in Organic Chemistry:  The Official Guide

    Examinations Institute / ACS / Division of Chem. Ed.

    ISBN 0-9708042-1-0

    http://www4.uwm.edu//chemexams/





   


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