Central Topic: Aldehydes & Ketones

                        ALDEHYDES & KETONES (C=O)
                               |
          ┌────────────────────┼────────────────────┐
          |                   |                    |
    STRUCTURE           REACTIONS              DISTINCTION
    PROPERTIES          (4 types)               TESTS
          |                   |                    |
   sp2 C, planar     ┌────────┼────────┐      ┌────┼────┐
   C^δ+, O^δ-        |        |        |      |    |    |
   Polar C=O      NUCL.    CONDEN-  REDUC-  2,4-  TOL- FEH-
                  ADDN.    SATION   TION    DNP   LENS LING
                     |        |        |
              ┌──────┤   ┌────┼────┐   ├──NaBH4/LiAlH4 → ALCOHOL
              |      |   |    |    |   ├──Clemmensen → CH2 (acidic)
           HCN     MgBr Aldol Hal. Cann └──Wolff-Kishner → CH2 (basic)
                   addn cond  form izza
                              |
                         Iodoform
                         CH3CO- → CHI3

Branch: Aldol Condensation

• Requires alpha-H
• Dilute NaOH
• Products: beta-hydroxy aldehyde → (heat) → alpha,beta-unsaturated aldehyde

Branch: Cannizzaro

• NO alpha-H required
• Concentrated NaOH
• Products: RCOO-Na+ (oxidized) + RCH2OH (reduced)
• Examples: HCHO, C6H5CHO, (CH3)3CCHO

Branch: Haloform

• Methyl ketone (CH3CO-) or precursor
• I2 + NaOH
• Products: CHI3 (yellow) + RCOONa