Reactions of Aldehydes

Consider the possible reaction of an aldehyde such as propanal with each of the reagents shown in the column on the left. Indicate the type of reaction expected in each case. Each reagent row will have one best answer. Assume that the reagents may be present in excess.
Using propanal, draw the product expected from each reaction.

ReagentsReaction Type
No Reaction Observed
(No Product Isolated)		Oxidation
(To a Carboxylic Acid)		Reduction
(To a Primary Alcohol)		Simple Addition
(No Loss of Water)		 Formation of a
Secondary Alcohol		Imine
Formation		 Enamine
Formation		Acetal
Formation
CH3CH2OH
H+ catalyst, –H2O
H2O
( pH = 4 )
CH3NH2
H+ catalyst, –H2O
KMnO4
in aqueous base
CH3CH2MgBr
(workup with H3O+)
NaC≡CCH2CH2CH3
(workup with H3O+)
LiAlH4
(workup with H3O+)
NaBH4
in aqueous alcohol
HCN
( pH = 7.5 )
(CH3)2NH
H+ catalyst, –H2O
Jones' Reagent
CrO3 in aq. H2SO4

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