Formation of Aldehydes and Ketones

Consider the possible formation of an aldehyde or ketone product when each of the ten compounds in the column on the left is treated with each of the reagents shown in the top row. Check the designated answer box if you believe an aldehyde or ketone will be formed.
Assume that the reagents may be present in excess. For each checked reaction, try to draw the structure of the major product(s).

Starting
Material
Reagents
PCC
C5H5NHCrO3Cl
Jones' Reagent
CrO3 in aq. acid
  Pb(OAc)4  
[ or HIO4 ]
(i) O3  
(ii) Zn dust
  H3O+ &  
HgSO4
(i) BH3 in THF
(ii) H2O2 + NaOH


 


   

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