CHM-235  Organic Chemistry I


Course Description:    Rigorous introduction to the chemistry of carbon-containing compounds.  Reaction mechanisms and recent methods of synthesis emphasized.
Prerequisites:    CHM152 and CHM152LL; or CHM154 and CHM154LL.


Course Materials:      


Here is a link for molecular model kits. 

    http://www.indigo.com/models/gphmodel/foundation-molecular-model-set-68845NV.html
          This kit has orbital paddles.

    www.darlingmodels.com
          There are a few different versions of the Molecular Visions Organic Set (Kit 1, 1A, or 2A).
          These sets are cheaper (~$14.00) but do not have orbital paddles.

As with all purchases, shop around.  If you find another good website, let me know.


Announcements

 

The Thanksgiving holiday is on Thursday, November 26th, not on November 25th.

There will be class on Wednesday, November 25th.

 

Exam #4 has been moved to Monday, November 23rd, not this Wednesday.

 

Change of venue for my Tuesday office hours:  I will have my Tuesday 5:30-6:30pm office hours

in PS-149 as a review session for CHM 235 – this is open to anyone in CHM 235 or anyone who

wants a refresher for CHM 235 material.

 

 

More problem sets: (from the Smith text). 

 

 

Problem Sets (from Smith text)

 

Chapter 1

     Review on atoms and electrons:  1, 2

     Bonds:  3, 4, 30, 31, 36, 68

     Structures:  5, 6

     Hybridization:  17, 18, 19, 26, 27, 28, 29, 63, 64, 65, 66, 67

     Electronegativity:  32, 33, 34, 73, 74, 75

     Charges:  7, 8, 37, 38, 39

     Other problems:  35, 76, 77, 78, 79, 80

     Resonance:  10, 11, 12, 13, 14, 15, 45, 46, 47, 49, 50, 52, 53, 82

     Structures:  9, 16, 20, 21, 22, 23, 24, 25, 40, 41, 42, 54, 55, 56, 57, 58, 59, 60, 61

 

Chapter 2

     Acid/base definitions:  1, 3, 23, 24, 25, 49, 50

     Reactions of acids and bases:  5, 6, 11, 12, 16, 27, 30, 31, 32, 51, 52

     Relative acidity:  7, 9, 10, 13, 14, 15, 19, 20, 22, 38, 44

     Conjugate acids/bases:  28, 29

 

Chapter 3

     Functional groups:  1, 2, 3, 15

     Intermolecular forces:  4, 5, 6, 9, 10, 11, 12, 17, 18, 19, 20, 21, 22, 23, 26, 27, 28, 30, 33, 34, 35, 36

     Isomers:  16

     Other problems:  41, 42

     More problems:  6, 7, 24, 29, 32

 

Chapter 4

     Alkane structure:  1, 2

     Isomers:  5, 6, 8, 39, 59, 60

     Nomenclature:  11, 12, 13, 14, 40, 41, 42, 43

     Types of C and H:  3, 4, 7, 37, 38

     Conformational analysis:  21, 22, 23, 24, 25, 44, 47, 48, 49, 50, 53

     Newman projections:  20, 51, 52

     Nomenclature:  39

     Substituted cycloalkanes:  15, 16, 17, 29, 30, 31, 32, 54, 55, 58, 70

     More problems:  18, 19, 26, 27, 28, 45, 46, 56, 57, 61

 

Chapter 5

     Isomers:  1, 2, 16, 17

     Chirality:  3, 4, 5, 6, 7, 8, 9, 10, 11

     Nomenclature:  12, 13, 14, 15, 41, 42, 43, 44, 45

     Enantiomers/diastereomers:  18, 19, 20, 21, 22, 23, 24, 25, 39

     More isomers:  26,33, 34, 35, 36, 37, 38, 40, 46, 47

     Other problems:  48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 62, 64

 

Chapter 6

     Reaction types:  1, 23

     Predicting products:  2, 24

     Mechanisms:  3, 25, 26, 30, 42

     Thermodynamics:  7, 8, 9, 10, 11, 12, 13, 35

     Transition states:  14, 15, 38

     Other problems:  51

 

Chapter 7

     Types of halides:  1, 2, 43

     Nomenclature:  3, 4, 41, 42, 44

     Substitution reactions:  8, 9, 46, 47

     Nucleophiles and leaving groups:  10, 11, 12, 13, 17, 48, 49, 50, 51, 52, 53

     Sn2:  18, 19, 20, 21, 22, 23, 55, 56, 57, 58, 69

     Solvent:  14, 54, 71

     Sn1:  25, 26, 27, 28, 29, 30, 59, 60, 61, 62, 63, 64

     Sn1 vs. Sn2:  31, 32, 33, 35, 36, 37

     Syntheses:  39, 40, 73, 75

     Mechanisms:  54, 65, 67, 68, 70

     More problems:  38, 74

 

Chapter 8

     Predicting products:  1, 19, 23, 25, 26, 49, 51

     Alkene classification:  2, 3, 4, 5, 6, 27, 28, 29, 30, 31

     Mechanisms:  7, 8, 13, 17, 18, 24, 52, 53, 55

     E2:  9, 10, 12, 20, 33, 34, 37, 38, 39, 44, 45

     E1:  14, 40

     E1 vs. Sn1:  16

     E1 vs. E2:  21, 41, 42, 43

     Other problems:  54, 56, 57, 58

 

Chapter 9

     Structures:  1

     Nomenclature:  2, 3, 4, 5, 38, 39, 40, 41

     Physical properties:  6, 7, 8, 42

     Preparation:  11, 12

     Reactions:  13, 14, 15, 18, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 43, 44, 45, 46, 47, 48, 49, 53, 58, 61

     Mechanisms:  16, 17, 19, 20, 33, 34, 50, 52, 54, 55, 56, 57, 62

     Syntheses:  51, 59, 60

 

Chapter 10

     Structures:  1, 41

     Nomenclature:  4, 5, 34, 35, 36, 37, 38, 39

     Stereochemistry:  6, 7, 8, 20

     Preparation:  11

     Electrophilic addition:  12, 14, 17, 18, 19, 22

     Mechanisms:  13, 16, 21, 24, 27, 44, 55, 57, 58, 59, 62, 65

     Reactions:  32, 46a-f, 46i, 47a-f, 48, 50a-e, 50h, 52, 53a-f

     Syntheses:  33, 49, 63a-b, 63e

    

 

http://www.molsci.ucla.edu/pub/explorations.html

 

 

 

Problem Sets (from McMurry text, Spring 2008)

Chapter 1
    Electron configuration:  1, 2, 21, 22, 27, 45
    Hybridization:  10, 11, 13, 14, 15, 16, 24, 25, 30, 31, 32, 39, 40, 41, 43, 44, 46, 47, 48

    Formulas:  5, 7, 23, 28, 34

    Structures:  18, 19, 20, 27, 29, 33, 36, 37, 38, 49, 50, 51, 52

    Drawing:  3, 4, 8, 9, 12, 17, 18, 19

    More structures:  6, 26, 28, 35

 

Chapter 2

    Bond polarity:  1, 2, 3, 4, 29, 30

    Overall polarity:  5, 6, 31, 32, 33, 34, 26, 60

    Charges:  8, 9, 35, 44

    Resonance:  10, 36, 37, 38, 56, 57, 61

    Acidity:  11, 12, 14, 15, 17, 18, 39, 40, 41, 42, 43, 45

    More acid/base problems:  13, 46, 47, 48, 49, 55

    Structures:  20, 21, 22, 23, 24, 25, 27, 28

 

Chapter 3

    Functional Groups:  1, 2, 3, 21, 29, 30, 35, 24

    Isomers:  4, 5, 6, 7, 25, 26, 27, 28, 31, 42

    Nomenclature:  11, 12 13, 14, 39, 45, 46, 47, 39

    Structures:  36, 37, 38, 61

    Types of C and H:  8, 9, 10, 32, 40, 41, 44

    Haloalkanes:  33, 34

    Cycloalkanes:  15, 16, 17, 18, 19, 20, 23, 43, 50, 51

    More nomenclature:  22, 48, 49

    Isomers:  52, 53, 54, 55, 59, 60

    Other problems:  56, 57, 58

 

Chapter 4

    Conformations:  1, 2, 3, 4, 5, 24, 25, 26, 27, 28, 29, 30

    Ring strain:  6, 7, 8, 9, 10

    Cyclohexane chairs:  11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 31, 32, 33, 34, 35, 36, 37, 38

    Biomolecules, 39, 40

    Cyclohexane boats:  19

 

Chapter 5

    Reaction type:  1, 24

    Nucleophiles and electrophiles:  4, 5, 20

    Mechanisms:  6, 7, 8, 9, 18, 19, 26, 39, 40, 41, 42, 44, 47, 50

    Thermodynamics:  10, 11

    Energy diagrams:  16, 17, 21, 22, 27, 28, 29, 30

    Functional groups:  23

    Other questions:  25, 48, 49

 

Chapter 6

    Nomenclature:  4, 5, 6, 20, 26, 27, 28, 29, 30, 31, 32, 41. 43

    Isomerism:  7, 8, 9, 10, 11, 12, 21, 42, 44, 45

    Alkene stability:  13, 33, 34, 35

    Addition of hydrogen halides:  14, 15, 16, 17, 18, 39, 40

    Mechanisms:  19, 48, 49, 50, 52

    Carbocations:  22, 47, 53

    Alkene structure:  37

    Other reactions:  56, 57

 

Chapter 7

    Addition of halogens:  3, 4, 54

    Addition of water:  7, 8, 9, 10, 11, 21, 22, 27, 41, 48, 55, 56

    Hydrogenation:  13

    Polymerization:  17, 18, 46, 47

    Halohydrin formation:  49

    Reactions:  23, 24, 25, 26, 50, 58

    Addition of acids:  35

    Carbenes:  12, 42, 51

    Oxidation:  14, 15, 16, 20, 28, 30, 33

    Other problems:  29, 31, 32, 34, 36, 38, 40, 43, 44, 45, 52

    Mechanisms:  37

    Elimination reactions:  1, 2

 

Chapter 8

    Nomenclature:  1, 2, 19, 20, 21, 40

    Addition reactions:  3, 4, 5, 6, 7, 8, 22, 23

    Oxidation:  9, 31

    Acidity:  10

    Syntheses:  11, 12, 13, 14, 30, 32, 33, 34, 35, 36, 37

    Structures:  18, 47

    Reactions:  24, 25, 26, 27, 28, 29, 41, 42, 43

 

Chapter 9

    Chirality:  1, 2, 3, 4, 32, 33, 34, 35, 36, 37, 38, 43, 44, 45, 46, 47, 48, 49, 51, 52, 54, 55, 56, 57, 74

    Nomenclature:  6, 7, 8, 9, 10, 28, 30

    Diastereomers:  11, 12, 13

    Meso compounds:  14, 15, 16, 29, 53

    Stereoisomers:  17, 19, 27, 39, 40, 41, 42, 50

    Reactions:  61, 62

 

Chapter 10

    Nomenclature:  1, 2, 14, 17, 18

    Radical Halogenation:  3, 5, 7, 15, 19, 24, 25, 32

 

Chapter 11

    Sn2 inversion:  1, 2, 3, 23

    Sn2 reactions:  4, 7, 26, 30, 36, 37, 38, 39, 40, 41, 51

    Nucleophiles:  5, 32

    Leaving Groups:  6

    Sn1 reactions:  8, 10, 11, 12, 13, 35

    Reactions:  14, 31, 43, 44

    Mechanisms:  54, 55, 62, 69

    Eliminations:  15, 16

    E2:  17, 18, 19, 45, 49, 65

    E1:  46

    Reactions:  20, 25, 33, 50

    Syntheses:  29, 34, 42, 64

 

Chapter 12

    Mass spectra:  5, 25, 29, 30

    IR:  6, 7, 10, 11, 12, 13, 14, 15, 34, 35, 37, 38, 39, 40, 41, 42, 43, 45

    Interpreting spectra:  48, 49, 52, 53

 

Chapter 13

    H1 NMR (# of signals):  3, 14, 15, 31, 37

    H1 NMR (chemical shift):  16, 17

    H1 NMR (integrations):  18, 39

    H1 NMR (splitting):  19, 20, 21, 24, 40, 41, 42, 43

    C13 NMR:  6, 7, 8, 12, 25, 32, 34, 45

    Structure determination:  23, 26, 27, 44, 46, 47, 48, 49, 50, 51, 52, 53, 55, 56, 57, 58, 66, 67

 

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

 


   

   

 


Links:


Hybrid Orbitals    A couple of key points to remember:
    1 - If you add n atomic orbitals, you'll end up with n hybrid orbitals.
    2 - The hybrid orbitals formed will point as far apart as possible.
    3 - Remember that in the case of sp2 and sp hybrids there are unhybridized p-orbitals remaining.

For some alternate depictions of atomic orbitals, there are a many well-constructed websites.  Below are a few URL's you can check out.  I tried to stick to the less elaborate sites so that they could run on most computers.

Electron Motion  Why worry about orbitals and electron motion in the first place.

http://micro.magnet.fsu.edu/electromag/java/atomicorbitals/     This site shows images of s, p , d, and f atomic orbitals.  You can view them individually or several at a time.  Keep in mind that we will deal mainly with hybridization of just the s and p atomic orbitals.  Take a look at the f-orbitals just for fun.

http://www.orbitals.com/orb    This website has images of various atomic orbitals, but not just s, p , d, and f orbitals.  It even shows images of more complicated orbitals.

http://www.towson.edu/~ladon/carbon.html    This is a tutorial on the electron configurations in carbon atoms and it also deals with hybridized orbitals.


Some more interesting links:

    http://science.nasa.gov/Realtime/jtrack/3d/JTrack3d.html
             Choose your favorite satellite and see where it is.  This site shows the current location of
             hundreds of satellites in orbit around Earth.

    http://www.lehsd.k12.nj.us/Pinelands/slideshow/sld001.htm
             Read about my home state - Southern New Jersey.




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