Molecular Rearrangements in Synthesis

Four synthetic transformations (1 to 4) are shown here. Each of these has been carried out by a sequence of reactions, one of which involves a molecular rearrangement. A list of seven possible procedures is given to the right of the equations. Your job is to pick the sequence (or single reaction) that best achieves the selected synthesis. Your choices should be made by clicking an appropriate button.

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Reaction Conditions

  A (i) C6H5CO3H in CH2Cl2; (ii) LiAlH4 in ether; (iii) H2O

  B (i) LiAlH4 in ether; (ii) H2O; (iii) C6H5CO3H in CH2Cl2

  C H2SO4 (catalyst) in CH3CN

  D (i) NH2OH (oxime formation) (ii) strong acid or PCl5 (Beckmann rearrangement)

  E NH4OH + NH4Cl in water; heat to reflux

  F (i) N2H4 (excess) (ii) HNO2; H3O(+); 5 C

  G (i) C7H7SO2Cl in pyridine (ii) Acetone + H2O, 50 C
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This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.