Categorizing reactivity by oxidation state
Major concepts
 In organic chemistry, it is useful to group functional groups into oxidation states: alkane,
alcohol, ketone, carboxylic acid, carbon dioxide.
 Reduction can be recognized by the net gain of C-H bonds or loss of C-Q bonds; oxidation can be
recognized as the net gain of C-Q bonds or loss of C-H bonds.
Vocabulary
 Oxidation state
 Redox reaction
Students should be able to:
 Be able to group functional groups into distinct oxidation states
 Know the type of mechanism(s) that are active within each oxidation state
Daily Problems
1. In the chart below, fill in the names of each redox category, starting with the most reduced on the
left. Then fill in the following functional groups in each category:
Alcohol, phosphate monoester, thioester, alkene, carboxylic acid, alkane, enol, acetal, amine, alkyl
halide, alkyne, ketone, aldehyde, ester, amide, imine
2. Fit each of the following mechanisms into redox categories listed in problem #1: electrophilic
addition, nucleophilic substitution, elimination, nucleophilic addition, nucleophilic acyl substitution
3. Organize the following molecules into groups according to oxidation state, starting with the most
reduced group on the left.