Unit 3: Organic Chemical Pathways (chapter 14) From Organic Molecules to spirin!

ASPIRIN
Aspirin: a common "rug use" to treat pain# $e%er an" in$lammation# an" to re"uce &loo" clotting! lso 'nown as acetylsalicylic acid. - Salicin: naturally occurring su&stance $oun" in lea%es an" &ar' o$ willow trees an" her& mea"owsweet! - 400BCE: (ippocrates ()ree' physician) *in$usion o$ willow lea%es an" &ar' to relie%e aches# pains# in$lammation an" $e%er!+ - 1829: acti%e ingre"ient# salicin isolate"! - 18!0: "octors prescri&e salicylic aci" "irectly ci"ic nature Unpleasant taste ,rritate" lining o$ mouth an" stomach! - 189!: synthesi-e" impro%e" mo"i$ication o$ salicylic aci" Feli. (o$$man ()erman /ayer Company) 0eplace "ydr#$yl $unctional group with ester $unctional group to $orm acetylsalicylic acid! - 191% &&I: )eorge 1icholas (Mel&ourne pharmacist) mar'et * spro+ /ritain una&le to o&tain aspirin $rom )erman 234 444 rewar" $or manu$acturer! /o"y con%ert salicin to salicylic aci"! 5alicin salicylic aci"! Salicylic acid: chemical use" to ma'e acetylsalicylic aci"! cti%e ingre"ient 0e"uce $e%er Anal'esic: a "rug that relie%es cts as e$$ecti%e anal'esic pain! Synt"etic pat"(ay: a series o$ chemical reactions re6uire" to pro"uce a wante" material# o$ten starting $rom simpler su&stances! 3 organic molecules use" to ma'e new organic molecule! 0eaction to $orm salicylic aci" (slow an" low yiel" water "ri%es reaction &ac'war"s): Car)#$ylic acid * alc#"#l ester * (ater. +ydr#$yl group $unction as alc#"#l in reaction with et"an#ic acid (acetic aci")! lternate pathway ($aster an" high yiel"): Et"an#ic acid replace" with et"an#ic an"ydride (acetic anhy"ri"e)

Unit 3: Organic Chemical Pathways (chapter 14) From Organic Molecules to spirin!

Ethanoic acid + ethanoic acid ethanoic anhydride + water Ethanoic anhydride + salicylic acid acetylsalicylic acid + ethanoic acid C2H4O2 + C2H4O2 C4H6O3 * (3O C4H6O3 + C7H6O3 C9H8O4 * C2H4O2 Unreacte" et"an#ic an"ydride con%erte" to et"an#ic acid &y a""ition o$ (ater cetylsalicylic aci" an" acetic (ethanoic) aci" separate" an" puri$ie"! Acetylsalicylic acid: * 7irtually tasteless 8ess irritating to stomach than salicylic aci"! 0eacts with water in stomach (hy"rolyses) in al'aline con"itions! 0eturn to more e$$ecti%e salicylic aci"! +ydr#lyses: &rea' "own (a compoun") &y chemical reaction with water! cetylsalicylic aci" hy"roly-e" in small intestine to salicylic aci"!

S,-.B-E ASPIRIN: - 1ot %ery solu&le in water - Con%ert car)#$ylic acid $unctional group to s#di/0 salt change molecule into ion - ,on: solu&le in water! - /u$$ere" aspirin pro%i"e $urther protection against stomach irritation! - B/11er: a solution that resists changes in p( when aci" or al'ali is a""e" to it! /u$$ers typically in%ol%e a wea' aci" or al'ali together with one o$ its salts!

Unit 3: Organic Chemical Pathways (chapter 14) From Organic Molecules to spirin!

5o"ium salt o$ acetylsalicylic aci"! P,-2ASPIRIN: - Polymer structure using con"ensation reaction &etween salicylic acid an" 1 8 3 #ctanedi#ic acid (su&eric aci")

(y"rolyse" to salicylic aci" in &loo"stream at small intestine! 9oesn:t irritate stomach Polymer &rea's "own slowly Controlle";release pain'iller Fight pain an" re"uce in$lammation e.actly where nee"e"! Polymer with similar molecular structure to polyester ma"e to threa" an" use" to stitch cuts an" woun"s Plastic coating $or in<ure" &one=<oint promote &one growth! ,n salicylic aci" an" acetylsalicylic aci"# some hy"rogen atoms on &en-ene rings replace" &y other $unctional groups! /en-ene un"ergo su&stitution reaction hy"rogen replace" (rather than a""ition reactions where "ou&le &on"s are &ro'en)