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D. PAVIA CHEM 352

D. PAVIA CHEM 352. SAMPLE EXAM TWO. 1. Name the following compounds by both IUPAC and common names, except as noted. IUPAC. COMMON. IUPAC. COMMON. omit. omit. 2. From the following pairs, pick (circle) the one from each pair that is:. a) the best nucleophile in DMSO.

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D. PAVIA CHEM 352

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  1. D. PAVIA CHEM 352 SAMPLE EXAM TWO 1. Name the following compounds by both IUPAC and common names, except as noted. IUPAC COMMON

  2. IUPAC COMMON omit omit 2. From the following pairs, pick (circle) the one from each pair that is: a) the best nucleophile in DMSO Cl- or Br- b) the best SN2 solvent H2O or acetone c) the best SN1 solvent ethanol or cyclohexane

  3. 3. Pick the substrate that will react fastest in an SN2 reaction. a) b) 4. Pick the substrate that will react fastest in an SN1 reaction. a) b)

  4. 5. Draw the major product that is expected (include stereochemistry if important) and, using the box predict whether these reactions will proceed by an SN1, SN2, E1 or E2 mechanism (major product). (R) (S)

  5. (R)

  6. 6. Cyclopropyl bromide will not react by either an SN1 or an SN2 mechanism. Using drawings of the critical transition state and/or intermediate as part of your explanation, explain why cyclopropyl bromide is so unreactive. 7. Show how to accomplish the following conversions. a) (R) (R) b) (R) (S)

  7. 8. Draw the stereochemical result in each case. PCl3 SOCl2 pyridine SOCl2 ether 9. Show how to synthesize the following compounds starting from acetylene.

  8. 10. Draw the result (including stereochemistry) at each stage of the following sequence. (R)

  9. 11. Draw the result (including stereochemistry) at each stage of the following sequence. (R)

  10. 12. Give a mechanism for the following reaction.

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