Chem 1120 Quiz 2

Instructions: This quiz is open-book. You may use any book, magazine, or other printed or web-based materials you feel are helpful. You may discuss this quiz with other members of this immediate class and section. You may not discuss, receive help on, or work on this quiz with tutors, friends, family members, or any one outside of class without my explicit permission. Violation of this stipulation is academic misconduct and is grounds for dismissal from class. You must work the quiz in its entirety by yourself before meeting in groups to compile a group quiz. I will award extra credit (5 pts) to those who work in groups of 2-5 and who submit a group quiz. You must show all your work for full credit, or to receive partial credit if you make a mistake.

Show all of your work and answers for this quiz on a separate sheet of paper stapled to this page. I do not require your work to be typed, but neatness and legibility do count.

  1. (6 points) Provide a structure for each of the following compounds, identify any polar bonds within the molecule, and identify all of the possible intermolecular bonding forces: Use your text to find electronegativity values.
    1. 1,4-pentadiene
    2. 1-fluoropropane
    3. 2-methyl-2-hexanol
    4. 1,1-dimethylcyclopentane
    5. pentanal
    6. butanoic acid
  2. (6 pts) A recently discovered compound was found to have the molecular formula C12H21N. What combination of structural features may a molecule with this molecular formula have? Hint: do not bother trying to look this compound up. Think double bond equivalence. There are at least 12 possibilities.
  3. (8 pts) Draw molecular structures for the following geometric isomers of 1,6-dibromo-1,3,5-hexatriene: ZZZ, ZZE, ZEZ, EZZ, ZEE, EZE, EEZ, and EEE. Be careful with the bond angles in your structures.
  4. (2 pts) Show the complete pathway for the reaction of 2-methyl-2-butene with chlorine. Identify the Lewis acids and bases, draw the structures of all organic products, correctly name them, and identify the major and minor products if they exist.
  5. (2 pts) Show the complete pathway for the reaction of 2,4,4-trimethyl-2-pentene with water in the presence of an acid. Identify the Lewis acids and bases, draw the structures of all organic products, correctly name them, and identify the major and minor products if they exist.
  6. (2 pts) The treatment of an organic compound with ozone resulted in the formation of acetone (2-propanone) and 4-methyl-2-pentanone. Identify the original compound and draw its skeletal structure.