Chem

 345  –  Organic  Reactions  Chapter  19  

Prepared  by  José  Laboy,  MS  
http://www.chem.wisc.edu/areas/clc  (Resource  page)  
 
Aldehyde  and  Ketone  Reduction  
 
Reaction:  
O
 
  1) LiAlH4
  H 3C H 2) Acid workup OH

  or
Aldehydes  are  reduced  to  1o  alcohols  
  NaBH4 / CH3OH
Ketones  are  reduced  to  2o  alcohols  
 
Mechanism:  
 
  O O Li
H

  + Al

 
H H
H
H C 3 H H 3C

  H

  H

  H Al H
Li

  H
 
H H
 
Al Li   Li and Al salts
O H O O
H
 
H
Li Al
4 H 3C OH
 
H O
H 3C
H
3  more  times  
O O
 
H
  Occurs  during  
  acid  workup  
 
  The  reduction  of  an  aldehyde  or  ketone  is  like  another  addition  reaction  to  
carbonyls.    Either  reagent,  LiAlH4  or  NaBH4  will  do  the  job.    Use  of  H2  under  high  
pressure  in  the  presence  of  a  precious  metal  can  also  provide  a  reduction.  
 
  O OH

 
  H2 102 atm / Ni

 
 
  Because  of  the  harsh  conditions  necessary  to  reduce  the  carbonyl  groups  
using  catalytic  hydrogenation  milder  conditions  will  selectively  hydrogenate  alkene  
compounds,  e.g.,  H2  /  Pd(C).  
 
O
  O

  H2 / Pd (C)
  Room Temp.