ORGANIC CHEMISTRY 2

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ORGANIC CHEMISTRY 2

• SPRING 2004
• MID-TERM EXAMINATION

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• Write a mechanism for each of the following
  reactions, paying attention to stereochemistry
  where appropriate
• 1a

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• Predict the product(s) of the following
  reactions, paying attention to stereochemistry
  where appropriate. Full credit may be obtained
  for the correct product, but partial credit may
  be obtained for a mechanism heading in the right
  direction if the product is wrong.

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• Protonate each of the following alkenes to give
  the most stable carbocation.

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• How would you accomplish the following
  conversions? They require more than one step.

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• Identify the sites of electrophilic
  monodeuteration of each of the following by
  D2SO4.

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• 6a
• The reaction of 3,3-dimethyl-1-butene, A, with
  aqueous acid gives a mixture of two alcohols.
  Give their structures and account for their
  formation.

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• 6b
• Cyclopentadiene on storage gives a dimer, which
  on heating regenerates the monomer. Suggest a
  structure and write a mechanism.

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