The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride_ A Novel Preparation for the Und

The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride_ A Novel Preparation for the Und

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Unformatted text preview: Vol. 74 No. 12 December 1997 • Journal of Chemical Education 1465 I n t h e L a b o r a t o r y Th e D i e l s–A l d e r R ea c t i on o f 2 , 4-H e x a d i e n-1-o l w i t h M a l e i c Anhydr i d e A Nov e l Pr e p a r a t i on f or t h e Und e rgr a du a t e Org a n i c Ch e m i s t ry L a bor a t ory Cours e Keith F. McDaniel* and R. Matthew Weekly Department of Chemistry, Ohio University, Athens, OH 45701 The ideal undergraduate o rgani c c hemistry lab o rat o ry experiment inv o lves several imp o rtant co mp o nents. These co mp o nents in c lude the examinati o n of o ne o r m o re inter- esting and hist o ri c ally imp o rtant rea c ti o ns t o pr o vide an interesting o rgani c m o le c ule, stimulating yet c hallenging 1 H nu c lear magneti c res o nan c e ( NMR ) and in f rared ( IR ) spe c tr o s co pi c data analysis, and a straight fo rward and co n- sistently repr o du c ible experimental pr oc edure that c an be co mpleted within a typi c al lab o rat o ry time f rame. In additi o n, an element of the unkn o wn is imp o rtant, t o all o w student input int o the experiment and av o id the coo kb oo k aspe c t of many typi c al undergraduate lab o rat o ry experiments. A n ex- periment that has been c arried o ut in o ur o rgani c lab o ra- t o ry co urse fo r the past several years co ntains ea c h of these co mp o nents, as it inv o lves b o th a Diels– A lder rea c ti o n and the ring-o pening of a c y c li c anhydride, 1 H NMR data that all o w utilizati o n of b o th 1- D and simple 2- D experiments, and fo rmati o n and is o lati o n of an analyti c ally pure c rystal- line pr o du c t within o ne h o ur. The Diels– A lder rea c ti o n c learly is o ne of the m o st im- p o rtant o rgani c rea c ti o ns taught t o undergraduate o rgani c c hemistry students, and m o st undergraduate o rgani c text- b oo ks co ntain se c ti o ns o n the rea c ti o n ’ s me c hanism, stere o- c hemi c al o ut co me, and o verall s co pe and limitati o ns ( 1 ) . The m o st co mm o n Diels– A lder rea c ti o n c arried o ut in under- graduate o rgani c c hemistry lab o rat o ries inv o lves the rea c- ti o n between c y c l o pentadiene and malei c anhydride ( 2 ) . A l- th o ugh this rea c ti o n w o rks quite well and generates a pr o d- u c t that is is o lated easily, c ra c king of the c y c l o pentadiene dimer is a nuisan c e, and the pr o du c t generated by this re- a c ti o n gives a 1 H NMR spe c trum that is di ff i c ult fo r students t o analyze co mpletely. A n o ther imp o rtant t o pi c in all undergraduate o rgani c c hemistry textb oo ks is the additi o n / eliminati o n rea c ti o n of c arb o xyli c a c id derivatives ( 3 ) . Nu c le o phili c atta c k o n anhydrides, a c id c hl o rides, esters and amides typi c ally is examined, and inter co nversi o n of these f un c ti o nal gr o ups is presented. M o st undergraduate o rgani c c hemistry lab o- rat o ry texts co ntain simple esteri f i c ati o n rea c ti o...
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The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride_ A Novel Preparation for the Und

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