Problem: With current spectroscopic techniques (discussed in Chapters 15–17), chemists are generally able to determine the structure of an unknown organic compound in just one day. These techniques have only been available for the last several decades. In the first half of the twentieth century, structure determination was a very slow and painful process in which the compound under investigation would be subjected to a variety of chemical reactions. The results of those reactions would provide chemists with clues about the structure of the compound. With enough clues, it was sometimes (but not always) possible to determine the structure. As an example, try to determine the structure of an unknown compound, using the following clues: The molecular formula is C4H10N2. There are no π bonds in the structure. The compound has no net dipole moment. The compound exhibits very strong hydrogen bonding. You should note that there are at least two constitutional isomers that are consistent with the information above. (Hint: Consider incorporating a ring in your structure.) 

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With current spectroscopic techniques (discussed in Chapters 15–17), chemists are generally able to determine the structure of an unknown organic compound in just one day. These techniques have only been available for the last several decades. In the first half of the twentieth century, structure determination was a very slow and painful process in which the compound under investigation would be subjected to a variety of chemical reactions. The results of those reactions would provide chemists with clues about the structure of the compound. With enough clues, it was sometimes (but not always) possible to determine the structure. As an example, try to determine the structure of an unknown compound, using the following clues:

  • The molecular formula is C4H10N2.

  • There are no π bonds in the structure.

  • The compound has no net dipole moment.

  • The compound exhibits very strong hydrogen bonding.
    You should note that there are at least two constitutional isomers that are consistent with the information above. (Hint: Consider incorporating a ring in your structure.) 

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 1st Edition. You can also practice Organic Chemistry - Klein 1st Edition practice problems.