Jose Gonzalez C Pre-Lab #5 12/04/2013

Crossed Aldol Condensation

Objecti e
!ibenzalacetone "ill be #re#ared b$ t%e crossed or &i'ed Aldol condensation o( acetone and benzalde%$de) *odi+& %$dro'ide and a &i't+re o( et%anol and "ater ,alread$ #re#ared-. t%ese t"o co&#o+nds "ill ser e as t%e base and t%e sol ent. res#ecti el$. to s$nt%esize t%e #rod+ct desired)

/%eor$
0%at is an Aldol condensation1 Aldol reaction1 /%e aldol condensation re#resents a #o"er(+l 2eneral &et%od (or t%e constr+ction o( carboncarbon bonds. is one o( t%e central t%e&es o( or2anic c%e&istr$) 3n t%e (irst ste# t%e basecatal$zed ,*odi+& 4$dro'ide in o+r e'a&#le- aldol condensation reaction. eli&inates a #roton (ro& an al#%a carbon ,adjacent- to a carbon$l 2ro+# t%at (or&s a resonance-stabilized anion called an enolate. "%ic% t%en carries o+t n+cleo#%ilic attac5 at t%e carbon$l 2ro+# o( t%e reactant. 2i in2 an al5o'ide ion t%at abstracts a #roton (ro& "ater t%+s creatin2 an aldol reaction) /%e aldol #rod+ct o(ten +nder2oes (acile eli&ination o( "ater ,a de%$dration reaction-. a((ordin2 an 6.7-+nsat+rated carbon$l co&#o+nd as t%e (inal #rod+ct) 89- is *#ectr+&1 0ill %el# to deter&ine t%e di((erent conj+2ation s$ste&s ,absor#tion le els- bet"een t%e startin2 &aterial and t%e (inal #rod+ct)

:aterials
;enzalde%$de. acetone. 10< sodi+& %$dro'ide. et%anol)

Proced+re A) =eaction
1) Add benzalde%$de to a 125 &l >rlen&e$er (las5 "it% a &a2netic stirrin2 bar. t%en 3 &l o( benzalde%$de? 1 &l o( acetone? 25 &l o( @5< et%anol) 2) /%en add 30 &l o( 10< sodi+& %$dro'ide) 3) *tir "it% &a2netic stirrin2 bar (or 5 &in+tes) 4) Ailter t%e &i't+re b$ ac++& (iltration) Bo+ need to +se (ilter #a#er) 5) 0as% t%e solid "it% 20 &l o( "ater) C) !isconnect t%e r+bber t+be (ro& t%e (iltration (las5) /%en t+rn o(( t%e ac++&) D) ;rea5 +# t%e cr$stal &ass ,on lar2e (ilter #a#er-

E) 0ei2%) @) Calc+late #rod+ct $ield)

;) 89- is s#ectr+&
1) !issol e 10 &2 o( dibenzalacetone in 10 &L o( et%anol in an >rlen&e$er (las5) *%a5e t%e (las5 to &a5e s+re t%e sol+tion is %o&o2eneo+s) /rans(er 1 &L o( t%e sol+tion to a ne" (las5 and dil+te it to 10 &L "it% et%anol) 2) =ecord t%e 89- is s#ectr+& o( t%e co&#o+nd)