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Chemistry, 7/e
Raymond Chang, Williams College
Organic Chemistry

Internet Exercises

Spectrum database
(http://www.speclab.com/compound/chemabc.htm)

  1. There are three structural isomers called dichlorobenzene. Use the Spectrum database at http://www.speclab.com/compound/chemabc.htm to:
    1. Determine which of the three isomers is used as a fumigant and a moth protectant.
    2. If the isomer used as a fumigant can be detected by smell, how much of the compound would be present in a room that measures 10' by 10' by 8'?
Molecular Viewing Gallery
(http://www.dcu.ie/%7Echemist/pratt/pdb/gallery.htm)

  1. 3D models are useful because they allow you to see much more of the 3-dimensional aspects of a molecule than is obvious with a structural formula such as HOCH2CH(CH3)CH2CH3. The molecular viewing gallery allows you to see a number of molecules in 3D perspective and to rotate them (you will need the plug-in Chime). It is important to remember, however, that the conformation of atoms that you see in these molecule is not static; that is, rotation of groups about single bonds can lead to an arrangement of atoms that is not the same as the picture you see. Let's go to the Molecular Viewing Gallery at http://www.dcu.ie/%7Echemist/pratt/pdb/gallery.htm, and click on 2-methylbutan-1-ol.
    1. First, write a structural formula of the type shown above for this compound.
    2. Does this compound exhibit optical isomerism?
    3. Does this compound exhibit geometrical isomerism?
    4. Rotate the molecule until the OH group is on the right-hand side and vertical. Now draw a structure for the molecule as it would appear after you have rotated the ethyl group around the single bond between the second and third carbons. Is the number 4 (end) carbon closer to the oxygen now or farther away? Is this new arrangement of atoms a structural isomer of the compound as it is shown or is it a conformation?
    5. Now write a structural formula for the structural isomer of this compound.
ChemFinder
(http://chemfinder.camsoft.com/)

  1. Using ChemFinder at http://chemfinder.camsoft.com/, answer the following about nicotene:
    1. Is the compound cyclic or acyclic?
    2. Is it an acid or a base or likely to be neutral in aqueous solution?
    3. If nicotene were dissolved in a solution of HCl, what site, if any, would the proton attack?
    4. How does nicotene find its way into some sources of drinking water?
Spectrum database
(http://www.speclab.com/compound/chemabc.htm)

  1. Using Spectrum database at http://www.speclab.com/compound/chemabc.htm, answer the following about nicotene:
    1. Is the compound cyclic or acyclic?
    2. Is it an acid or a base or likely to be neutral in aqueous solution?
    3. If nicotene were dissolved in a solution of HCl, what site, if any, would the proton attack?
    4. How does nicotene find its way into some sources of drinking water?
nomenclature and stereochemistry site
(http://www.brunel.ac.uk/depts/chem/project/tutorial/nomen/nomen.htm)

  1. The Royal Society of Chemistry posts chemistry problems of various topics. Go to their nomenclature and stereochemistry site at http://www.brunel.ac.uk/depts/chem/project/tutorial/nomen/nomen.htm.
    1. What is the IUPAC name for the compound in question 6?
    2. In question 29, what functional group is present?
    3. In question 37, which compound has a chiral center?
hybridization and aromaticity
(http://www.cem.msu.edu/~parrill/ch15/hybridization.html)

  1. A vital site for organic chemistry students is at Michigan State University. Check out what they have on hybridization and aromaticity at http://www.cem.msu.edu/~parrill/ch15/hybridization.html.
    1. What functional groups are present in the second compound?
    2. What makes a compound aromatic?








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