Carboxylic Acids - Reactions - PowerPoint PPT Presentation

carboxylic acids reactions n.
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Carboxylic Acids - Reactions

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  1. Carboxylic Acids - Reactions Acid-base reactions: ion LDF H-bonding + NaOH Na+ + H2O octanoic acid sodium octanoate + water soluble insoluble in H2O dipole

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

  3. Reactions nucleophilic substitution H+ + + H2O carboxylic acid ester alcohol condensation reaction reverse = hydrolysis H+ + carboxylic acid alcohol ester + H2O

  4. Esters from alcohol from acid name = alkyl group from alcohol (yl) acid name changed to “oate” methyl butanoate apple pentyl butanoate peaches

  5. Esters H-bond acceptors O O no H-bond donor dipole-dipole interactions water soluble low b.p.

  6. Carboxylic acids nucleophilic substitution .. activator + + H2O carboxylic acid amide amine condensation reaction carboxylic acid amide + amine + H2O hydrolysis reaction amide + H2O carboxylic acid + amine

  7. Amines organic analogs of ammonia ammonia 1o amine 2o amine 3o amine N- all have H-bond acceptor H+ 1o and 2o have H-bond donor high b.p. electronegativity O N > liquid at room T gas at room T

  8. Amines nomenclature 1. Name and alphabetize R groups and add “amine” 1o methylamine ethyl methyl amine 2o ethyl dimethyl amine 3o low b.p.

  9. Amines weak bases + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]

  10. Amines nucleophilic substitution activator +H2O +H2O no reaction + amide 3o amine carboxylic acid 1o amine 2o amine amide Condensation reaction

  11. Amides very high b.p. and C-N double bond character C-O no rotation about C-O or C-N bonds molecule is flat and rigid structure of proteins