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CHEMISTRY 2600

CHEMISTRY 2600. Topic #9: Review Questions Spring 2009 Dr. Susan Lait. Reaction Wheels. Draw the product of each reaction below. 2. Reaction Wheels. Draw the product of each reaction below. 3. Reaction Web.

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CHEMISTRY 2600

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  1. CHEMISTRY 2600 Topic #9: Review Questions Spring 2009 Dr. Susan Lait

  2. Reaction Wheels Draw the product of each reaction below. 2

  3. Reaction Wheels Draw the product of each reaction below. 3

  4. Reaction Web • Connect as many of the compounds below as possible using reaction equations. Draw an arrow from the starting material to the product and list the reaction conditions. An example is given.

  5. HOMO/LUMO Interactions Would it be thermally allowed for an allyl cation or allyl anion to undergo a cycloaddition with acetonitrile? Why or why not? For any thermally allowed reaction, draw the product and indicate whether or not the reaction would be likely to proceed. 5

  6. Making Amines by Hydrogenation Acetonitrile reacts with hydrogen in the presence of a transition metal catalyst to give ethanamine. Draw three more compounds that react with hydrogen/catalyst to give ethanamine. 6

  7. Reaction with Bases Complete the table below to show the anion generated when each compound (at left) reacts with each base (in top row). If little-to-no reaction occurs, write “no reaction”. 7

  8. Synthesis Over 600 related compounds were screened in the process of developing ibuprofen as an alternative to aspirin. One of the compounds that was initially of interest is shown below. Propose a synthesis starting with 4-ethylphenol. 8

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