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Review

+. -. :. :. :. :. :. :. :. O. O. O. C. C. C. O. H. H. Nu. Nu. C. Review. ketone. aldehyde. C = O. very polar. Nucleophilic addition. -. H - Nu. +. +. H - OH H - OR H - NH 2. -. +. R. R. C O. C O. R. R. H. H. R. C O- H. R. O - H. R. R.

patrick-riley
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Review

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  1. + - : : : : : : : O O O C C C O H H Nu Nu C Review ketone aldehyde C=O very polar Nucleophilic addition - H-Nu + + H-OH H-OR H-NH2 - +

  2. R R .. .. C O C O R R H H .. .. R C O-H R O-H R R R .. .. .. C = O C = O C = O .. .. .. R R R .. O H H .. R R R + H+ R .. C + H2O O .. .. C R R H O - H C R O-H N N H H H N - H2 O-R H Nucleophilicaddition H+ + H+ H H+ hydrate or diol + H+ + H-OH + H-OR hemi-ketal + H-NH2 Schiffs base

  3. H H OCH3 CH3 H3C H3C C O C O H3C Addition of alcohol H+ CH3OH + H ketone + alcohol = hemi- ketal unstable aldehyde + alcohol = hemi- acetal unstable

  4. H .. .. OH - CH3 - CH2 .. .. H H H H3C H3C H3C OH OH O - CH2 - CH3 C C C O - CH2 - CH3 O - CH2 - CH3 O - CH2 - CH3 H .. O - CH2 - CH3 .. substitution Nucleophilic H+ .. H+ .. + H2O hemi - acetal + H+ aldehyde alcohol alcohol acetal + + condensation reaction acetal + H2O hemi-acetal + alcohol

  5. propanal + acetal 2 equivalents ethanol stable 2-butanone + hemi- ketal 1 equivalent methanol unstable

  6. H+ + cyclohexan one ethane diol H + H2O .. H+ .. .. H+ .. + H+ ketal hemi-ketal

  7. Carboxylic acids [O] [O] 1o alcohol aldehyde carboxylic acid methanol methanal methanoic acid H-bond acceptor - very high b.p. H-bond donor - + 2 H-bonds / molecule

  8. Carboxylic acids Nomenclature 1. Carboxyl group (COOH) always C1 2. Family name is longest C chain with COOH 3. Suffix is “-oic acid” 4. Carbonyl groups (C=O) called “oxo” Hydroxy groups (OH) called “hydroxy”

  9. O OH CH3 – CH2 – CH – C CH2 – CH3 CH3 – CH2 – CH – CH2 – CH – CO2H OH O CH2 – CH3 Carboxylic acids 4 3 2 1 2-ethyl butan oic acid 2-ethyl 4-hydroxy 6 5 4 3 2 1 2-ethyl- 4-hydroxy hexan oic acid 2-ethyl- 4-oxo hexan oic acid add [O]

  10. Carboxylic Acids Chemical properties = = OH Bronsted acid H+ donor C=O + HA H+ + A- H+ + weak acids, small dissociation Ka = [A-] [H+] Ka  1 x 10-5 pH 2.5 for 1M [HA]

  11. Carboxylic Acids H+ + H+ + - resonance structure anion stabilized

  12. - Carboxylic Acids acidity also affects solubility soluble short chain acids H-bonding long chain acids insoluble benzoic acid LDF soluble add a strong base (OH-) ion-dipole

  13. Reactions Acid-base reactions: + NaOH Na+ + H2O octanoic acid insoluble sodium octanoate + water soluble

  14. Reactions Reduction: LiAlH4 5 4 6 3 1 2 5-oxo hexanoic acid hexanediol 1,5- H2/ Pt NaBH4 5-hydroxy hexanoic acid

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