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

 

 

Here are some more problem sets: (from the Smith text). 

 

Here is the third take-home assignment – this one is due by 12:30pm this Monday (Feb. 8th).

 

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

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

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

 

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, 8, 9, 10, 11, 12, 17, 18, 19, 20, 21, 22, 23, 26, 27, 28, 30, 33, 34, 35, 36

     Isomers:  16

     Other problems:  6, 7, 24, 29, 32, 41, 42

 

Chapter 4

     Alkane structure:  1, 2

     Isomers:  5, 6, 8, 39, 59, 60

 

   

 

 

 

 

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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