Multistep Synthesis

One of the most challenging aspects of learning organic chemistry is devising sequences of reactions that will lead from a designated starting compound to a desired product compound. This problem is an introduction to the planning of multistep syntheses. For use, you have six reactant compounds (A through F); and eight reagents (1 through 8), shown below.
Following these lists, five multistep syntheses are outlined. For each of these, certain reactants or reagents must be identified by entering an appropriate letter or number in designated answer boxes. Enter a single letter or number, indicating your choice of the best reactant or reagent, in each answer box.

Reactant Compounds:


Reagents
1   Jones' reagent
  Na2Cr2O7 in H3O(+)
2   PCC
  CrO3 in pyridine + HCl
3   Sodium Hydride
  NaH
4   Sodium Borohydride
  NaBH4
5   Thionyl Chloride
  SOCl2
6   Phosphorus Tribromide
  PBr3
7   Aluminum Trichloride
  AlCl3
8   Magnesium
  Mg turnings in ether


 1) reagent
 2) Reactant

3)   H3O(+)  
 
C9H12O2  reagent

 


 Reactant
   reagent

 
C3H6O2  
 1) reagent    

 2) Reactant +
        reagent & heat


 1) reagent
 2) reagent

3)   CO2      
4)   H3O(+)  
C6H10O2  Reactant

heating with catalytic acid


 Reactant
  reagent

 
C3H6O  1) NaOH solution
  2) reagent    

  3) Reactant    
 


 Reactant
 1) reagent

 2) reagent
C3H7Br  1) reagent
 2) Reactant

3)   H3O(+)    
 



 

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.