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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
![Carboxylic acids [O] [O] 1o alcohol aldehyde carboxylic acid methanol](http://slideplayer.com./slide/14476413/90/images/1/Carboxylic+acids+%5BO%5D+%5BO%5D+1o+alcohol+aldehyde+carboxylic+acid+methanol.jpg "methanal. methanoic acid. H-bond acceptor. - very high b.p. H-bond donor. - + 2 H-bonds / molecule.")
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Carboxylic acids 2-ethyl butan oic acid 2-ethyl 4-hydroxy 2-ethyl-
CH3 – CH2 – CH – C CH2 – CH3 O OH 4 3 2 1 2-ethyl butan oic acid O CH3 – CH2 – CH – CH2 – CH – CO2H OH CH2 – CH3 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]
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Carboxylic Acids Chemical properties resonance structure
+ H+ + - resonance structure anion stabilized
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Carboxylic Acids soluble short chain acids H-bonding + NaOH
LDF H-bonding ion + NaOH Na+ + H2O octanoic acid sodium octanoate + water insoluble in H2O soluble dipole
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Reactions Reduction: 5-oxo hexanoic acid 1,5- hexanediol 5-hydroxy
LiAlH4 6 5 4 3 2 1 5-oxo hexanoic acid 1,5- hexanediol H2/ Pt NaBH4 5-hydroxy hexanoic acid
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Reactions nucleophilic substitution condensation reaction reverse =
+ + H2O carboxylic acid alcohol ester condensation reaction reverse = hydrolysis H+ + ester + H2O carboxylic acid alcohol
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Esters from alcohol from acid name = alkyl group from alcohol (yl)
acid name changed to “oate” methyl butanoate apple pentyl butanoate peaches
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Esters H-bond acceptors O O no H-bond donor dipole-dipole interactions
water soluble low b.p.
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Carboxylic acids nucleophilic substitution condensation reaction
.. heat + + H2O carboxylic acid amine amide condensation reaction carboxylic acid + amine amide + H2O hydrolysis reaction amide + H2O carboxylic acid + amine
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Amines N- H+ organic analogs of ammonia ammonia 1o amine 2o amine
all have H-bond acceptor N- 1o and 2o have H-bond donor H+ high b.p. electronegativity O N liquid at room T > gas at room T
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Amines nomenclature 1. Name and alphabetize R groups and add “amine”
methylamine 1o ethyl methyl amine 2o ethyl dimethyl amine 3o low b.p.
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Amines + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]
weak bases + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]
![Amines + H2O + OH- [R-NH3+] [OH-] smaller Kb weaker base Kb = [R-NH2]](http://slideplayer.com./slide/14476413/90/images/12/Amines+%2B+H2O+%2B+OH-+%5BR-NH3%2B%5D+%5BOH-%5D+smaller+Kb+weaker+base+Kb+%3D+%5BR-NH2%5D.jpg "weak bases. + H2O. + OH- [R-NH3+] [OH-] smaller Kb. weaker base. Kb = [R-NH2]")
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Amines Condensation reaction nucleophilic substitution +H2O +H2O
heat +H2O +H2O no reaction + amide carboxylic acid 2o amine 1o amine 3o amine amide Condensation reaction
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Amides C-O and C-N double bond character
very high b.p. C-O and C-N double bond character no rotation about C-O or C-N bonds molecule is flat and rigid structure of proteins
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![Oxidation of alcohols [O] = oxidizing agent dichromate Cr 2 O 7 2- permanganateMnO 4 - oxidation = aldehyde 1 o alcohol carboxylic acid 1. binding O 2.](/25/8041463/big_thumb.jpg "Oxidation of alcohols [O] = oxidizing agent dichromate Cr 2 O 7 2- permanganateMnO 4 - oxidation = aldehyde 1 o alcohol carboxylic acid 1. binding O 2.>")
