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The Diels-Alder Reaction: Preparation of 1,2,3,4-- 71-73

Tetraphenylnaphthalene on a Microscale
Name: Keith Philippe
TA: Kit Zall
Lab Section: 08
March 23, 2009
Introduction
The Diel!Al"er reaction i #enerall$ coni"ere" a precio% reaction in or#anic chemitr$
ince it re&%ire 'er$ little ener#$ to create a c$clohe(ane rin#) *n thi e(periment,
in'eti#ate the m%lti!tep $nthei o+ ,,2,3,-!tetraphen$lnaphthalene) The primar$
$nthei +or thi reaction .a the Diel! Al"er /eaction) The $nthei ma0e %e o+ a
broa" ran#e o+ or#anic laborator$ techni&%e to en%re p%rit$ an" $iel" thro%#ho%t the
proce"%re) The mot notable o+ thee are Diel!al"er, ben1$ne +ormation, an" ol'ent!pair
cr$talli1ation) An 2NM/ o+ the pro"%ct .a t%"ie", +oc%in# on the $mmetr$ o+ the
molec%le an" the ortho an" meta co%plin# ober'e" +or the aromatic h$"ro#en o+ the
naphthalene)
Mechanis !chee
Procedure
The proce"%re +ollo.e" .a a i "ecribe" in 3Laboratory Manual for Organic
Chemistry 23114, Se'enth 5"ition, "ane #$ %issin&er, Thompon 6%tom P%blihin#,
Maon, 7hio, 2''(, pp) 8,!83) Sli#ht mo"i+ication .ere ma"e in ma an" 'ol%me o+
reactant) 809 o+ the total ma an" 'ol%me o+ the reactant .ere %e" in the e(periment)
200 m# o+ tetraphen$lc$clopenta"ienone .a %e")
R#A)#*T+ PR,D-.T TA/0#
Tetraphenylclopentadienone /en1yne 1,2,3,4-Tetraphenylnapthalene
1
M% 388)-80 8: -32);;
)ras 0)200 NA 0),;3
Moles 0)000;2 NA 0)0003;
0 NA NA NA
1
Density
&+0
NA NA NA
1
/pt+pt,
'
.
NA< 2,8!220 NA NA< ,99!20,
=2a1ards Non!ha1ar"o%, minimi1e
e(po%re
NA Non!ha1ar"o%, minimi1e
e(po%re
Phys Prop$ 6r$talline p%rple oli" NA >hite cr$talline oli"
,
...)i#maal"rich)com=
Yield and Property Data for 1,2,3,4-Tetraphenylnapthalene
Theoretical
?l"
Act%al ?iel" 9 ?iel" @pt
0
6
@e+ore
/ecr$tali1ation
@pt
0
6
A+ter
/ecr$tali1ation
Appearance
0)200 # 0),;3 # 889 ,99);!200 20:!208 Aine .hite cr$tal
?iel" 6alc%lation:
ma Tetraphenylclopentadienone 0)200 #
ma 1,2,3,4-Tetraphenylnapthalene 0),;3 #
Theoretical ?iel" B 0)200 #)
Act%al ?iel" B 0),;3 #)
9 ?iel" B C0),;3 #< 0)200 #D ( ,009 B 889)
Results 3 ,4ser5ations
A+ter a""in# Tetraphen$lc$clopenta"ienone cr$tal .ith "imeth$lether CDM5D, the
re%ltin# ol%tion became "ar0 p%rple E the color o+ the tetraphen$lc$clopenta"ienone
cr$tal) -; min%te a+ter a""in# the tetraphen$lc$clopenta"ienone ol%tion to the
ioam$l nitrite an" anthranilic aci" ol%tion, there .a a chan#e in color +rom p%rple to
oran#e) The chan#e .a #ra"%al +or the +irt ,20 econ" then accelerate" to a $ello.
color) A+ter allo.in# the mi(t%re to it an" cool +or at room temperat%re, rei"%al cr$tal
be#an +ormin# aro%n" the .all o+ the tet t%be containin# the mi(t%re) A+ter a""in# a
+e. "rop o+ .ater a clo%"$ precipitate +orme" b%t &%ic0l$ "iappeare") A+ter a +e. more
"rop o+ .ater the precipitate be#an to lin#er lon#er be+ore "iappearin#) At thi point no
more .ater .a a""e" ince thi in"icate" p%re ,,2,3,-!tetraphen$lnapthalene can
cr$talli1e +rom the ol%tion once place" in an ice bath an" the i"e o+ the container are
cratche" perio"icall$) The ol%tion .a place" in a ;0 ml 5rlenme$er +la0, coole" in an
ice bath an" the i"e o+ the +la0 cratche" .ith a #la ro") Aine .hite cr$tal
imme"iatel$ +orme" in the proce) There .a ho.e'er, a 'er$, 'er$ +aint h%e o+ p%rple
on ome o+ the cr$tal) A+ter the cr$tal .ere +iltere" +rom the mother ol%tion, a
ample .a collecte" an" the meltin# point "etermine") The meltin# point ran#e .a
,99);!200
0
6 ) The pro"%ct coole" an" reoli"i+ie", a econ" meltin# point .a ta0en
#i'in# a meltin# point ran#e o+ 20:!208
0
6)
Ainall$, an 2NM/ ample o+ the pro"%ct .a ta0en Cre%lt appen"e"D)
1
2 *MR !pectroscopy 61,2,3,4-Tetraphenylnapthalene7
Proton, 2
(
6hemical
Shi+t, ppm
Splittin#
pattern
F 'al%e 21 *nte#ration
Area CcmD
G 2H
2
a
:)8; triplet 8)2 8)2 -
2
b
8)2- triplet 3): 9)2 8
2
c
8)39 m%ltiplet 3)2 ,); 8
2
(
8):3 m%ltiplet 3)- ,)- 2
2
$
8)2: triplet 3)- ;), 2
Note: Only protons useful in diffentiation included in table above. pectrum! ho"ever! includes others.
Calculation samples for H!" #pectrum:
,) 6hemical hi+t 2
b
B C8)2-8I8)230D<2B 8)2-
2) F 'al%e o+ 2
b
B C8)2-8!8)230D(200 21 B :)8
Discussion 3 .onclusion
*n the $nthei o+ $nthei o+ ,,2,3,-!tetraphen$lnapthalene,
tetraphen$lc$clopenta"ienone .a %e" a the "iene an" ben1$ne .a %e" a the
"ienophile) Propertie o+ ben1$ne Cincl%"in# maD .ere not peci+ie" beca%e the
ben1$ne interme"iate i 'er$ %ntable .hen +orme", an" there+ore imme"iatel$ reacte"
.ith the tetraphen$lc$clopenta"ienone preent to +orm the Diel Al"er a""%ct)
The Diel!Al"er $nthei an" ol'ent!pair cr$talli1ation %cce+%ll$ $iel"e" ,,2,3,-!
tetraphen$lnapthalene cr$tal) The percent $iel" b$ ma .a 889, that i, 0)2 #
Tetraphen$lc$clopenta"ienone $iel"e" 0),;3 # ,,2,3,-!tetraphen$lnapthalene) The lo.
proce %e" to obtain the cr$tal .a %cce+%l ince a +at proce i o+ten not
electi'e an" .o%l" ha'e allo.e" imp%ritie to +orm)
Meltin# Point @e+ore an" A+ter /ecr$talli1ation con+irme" that the ,,2,3,-!
tetraphen$lnapthalene cr$tal .ere near p%re) Literat%re in"icate" that the meltin# point
o+ the pro"%ct be+ore recr$talli1ation i bet.een ,99!20,
0
6) The mea%re" meltin# point
o+ the pro"%ct .a ,99);!200
0
6) Literat%re +%rther in"icate" that the meltin# point o+
,,2,3,-!tetraphen$lnapthalene a+ter reoli"i+ication .a 20-!20;
0
6) The e(perimental
meltin# point o+ the pro"%ct a+ter reoli"i+ication .a 20:!208
0
6)
2NM/ *nterpretation, *mp%rit$
,
2NM/ anal$i +%rther con+irme" the preence o+ ,,2,3,-!tetraphen$lnapthalene
Cpectr%m appen"e"D) All proton pea0, not incl%"in# that o+ 0no.n imp%ritie, in thi
cae, .ater, .ere locate" "o.n+iel" bet.een :); ppm E8 ppm) Thee pea0 are
characteritic o+ aromatic proton) The pectr%m +%rther e(hibit intene pea0 at 2
a
an"
2
b
o+ the branchin# phen$l %btit%ent) The relati'e tren#th o+ thee pea0 an" there
poition Ccloer %p!+iel" than other aromatic pea0 preentD in"icate" that thee proton
.ere the mot hi#hl$ hiel"e" an" there+ore m%t ha'e lie" at the mot "ital en" o+ the
phen$l %btit%ent) Similar 'icinal proton +or 2( an" 2c clearl$ e(hibit imilar pin!
pin co%plin# an" cone&%entl$ pea0 plittin#) Thee in"icate" the preence o+ t.o pair
o+ %ni&%e proton .ith onl$ one proton on nei#hborin# carbon atomCD) Thi pairin# alo
con+irm the tr%ct%re o+ ,,2,3,-!tetraphen$lnapthalene) The onl$ 0no.n imp%rit$ preent
in the ample .a .ater Cppm ,);D)
The 889 $iel" o+ the pro"%ct co%l" ha'e been increae" i+ a econ" an"< or thir" batch o+
cr$tal .a cr$talli1e" +rom the mother li&%or) *+ the e(periment .a con"%cte" once
more, e(traction +rom a""itional batche .o%l" be coni"ere") 7'erall, ho.e'er, the
e(periment .or0e" a "eire" an" the percent reco'er$ .a relati'el$ #oo")

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