Important reactions

Important reactions思维导图，包括：Reduction、Grignard addition、Dehydration、hydration、Protection、oxidation。

Important alcohol reactions

• Reduction
  • Products
    • Alcohols
      • treatment
        • 1. NaBH4 or LiAlH4
        • 2. H3O+
        • 3. nucleophile could view as a hyride ion H:-
      • 1' alcohol
        • by reactants
          • Aldehydes
            • nucleophilic addition
          • Carboxylic acids
            • nucleophilic acyl substitution
          • Esters
            • produce also R'OH
              • ester: RCOOR'
            • nucleophilic acyl substitution
          • ethers
            • cleavage by HX, H2O
              • SN2 when 1'/2' ether
              • SN1 or E1 when 3' ether
      • 2' alcohol
        • by reactants
          • Ketones
            • nucleophilic addition
    • aldehyde
      • reactant
        • ester
      • treatment
        • diisobutylaluminum hydride: DIBAH
• Grignard addition
  • Products
    • Alcohols
      • Treatment
        • 1. R'MgBr, ether
        • 2. H3O+
        • 3. neucleophile could view as R3C:-
      • 1' alcohol
        • by reactant
          • formaldehyde
            • nucleophilic addition
      • 2' alcohol
        • by reactants
          • aldehydes
            • nucleophilic addition
      • 3' alcohol
        • by reactants
          • Ketones
            • nucleophilic addition
          • Esters
            • produce also R''OH
              • ester: RCOOR''
            • nucleophilic acyl substitution
• Dehydration
  • products
    • C=CR2
      • by reactants
        • 3' alcohol
      • trearment
        • H3O+
        • E2
    • C=C
      • by reactants
        • 2' alcohol
        • 3' alcohol
      • treatment
        • POCl3
        • Pyridine
• hydration
  • nucleophilic addition of H2O
    • always reveriable by elimination/ dehydration
  • products
    • Gemdiol/hydrate(1,1-diol)
      • Aldehydes
      • Ketones
      • %99.9 diols their aqueous solution equilibrium
    • Subtopic
  • Catalysis
    • Acid catalysis
      • protonation of Carbonyl oxygen makes the carbonyl carbon more electrophilic
    • Base catalysis
      • hydroxide ion is more nucleophilic than water
• Protection
  • alcohol protection
    • -OH+Cl-SiR3(TMS)
      • form R'-O-SiR3
        • SN2 like mechanism
        • Inpresence of a base
      • removed by aquwous acids with fluoride ion
  • Ketone/ Aldehydes protection
    • Acetyl formation
• Oxidation
  • Products
    • Aldehydes
      • by reactants
        • 1' alcohol
      • Treatment
        • Dess-Martin periodinane
        • CH2Cl2
      • mechanism
        • E2 like
    • ketones
      • by reactants
        • 2' alcohol
      • Treatment
        • Dess-Martin periodinane
        • CH2Cl2
      • mechanism
        • E2 like
    • Carboxylic acid
      • by reactants
        • 1' alcohol
          • E2 like
        • Aldehydes
          • form hydrate intermediate
            • p 569
      • Treatment
        • CrO3
          • could also be KMnO4 and hot HNO3
        • H3O+, acetone
    • quinones
      • by reactants
        • phenols
      • Treatment
        • (KSO3)2NO
        • H2O
      • mechanism
        • Radical