medchem 17 Flashcards
carbolyxic acid deratives includes:
- esters (-OR)
- acid halids as acid chloride
- acid anhydride - ( -0-CO-R )
- amides (NH2,NHR , NR2)
aspirin is ester of —- as well as being a —–
- ethanoic acid
- carbolysic acid
carbolyix acid derives undergos —- and its different from —- and it has one — but ends up as —-
the rules are:
- nucleophilic substtuion
-sn2 - one tetrahedral intermediate ( 2 steps )
- triagonal product
- carbon needs to be a good electrophile
- leaving group needs to be better than nuelphile
- nucleophile needs to be strong enough
the leas reactive carbolyxic acid directives are —-
amide is the lest reactive
then ester
then acid anhydride
then acid chloride
cl
best leaving groups:
best nulephiles:
cl - > carboxylate > r-o- > -ve nitrogen > -ve carbon
-ve carbon > -ve nitrogen > nh3 aka ammonia > carboxylate > oh-r aka alcohol > cl-
acid chlorides undergo hydrolysis to produce:
alcholosis:
and aminolysis:
carboylix acid + hcl
ester + hcl
amide + hc;
( CHECK MECHANISMS )
charged nuclphioles are — than neautral ones so the reactions will be —
more nucleophilic
faster
symmetrical acid anhydride are produces by —–
addition of 2 carbolic acid and elimination of water
acid anhydride + water:
acid anudrid + alcohol:
acid anhydride + nh3:
- carbolyzic acid + ethanoic acid/acetic acid
- ester + ethanoic acid
- amide + ethanoic acid
aspirin is synthesised by reacting —– in the prrswenc of —-
salsilic acid and acid anhydride presence of h+
salsilic acid contains
carbolyxic group and hydroxyl group which can react with alcohol to produce aspirin aka the ester and water ( CHECK MECHANISM )
aspirin can be hydrolysed in —-
basic and acidic solutions
in acid solutions aspirin will produce:
in basic conditions aspirin produces :
- salsilic acid and ethanoic acid
- salsylic acid and sodium acetate
