Orgo 2 Lab Experiment 2 PDF

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Organic Chemistry 2 Lab Two Experiment...

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Reduction of racemic camphor to (1S)-(-)-borneol and (1S)-(+)-isoborneol

Ob j e c t i v e : Th eg o a lo ft hi ss e s s i o nwa st or e d u c ear a c e mi cc omb i n a t i o no fc a mp h o rt oami x t ur eo f d i a s t e r e o me r s ,( 1 S) ( ) b o r n e ola n d( 1 S) ( +) i s o b o r ne o l . Th i sr e d u c t i o nwa sa c c o mp l i s h e db y t h er e d uc i n ga g e n t . Wh e nt h eh y d r i d ei o no fs o d i u m s o di u mb o r o h y d r i d e , Na B H4 , b o r o h y d r i d ea t t a c kst h ee l e c t r o p h i l i cc a r b o no fc a mp h o r ’ sc a r b on y lg r ou p , b o t he nd o -a n de x o a t t a c k sc a no c c ur , a l t h o u g ho n ed i a s t e r e o me rwi l l f o r mp r e f e r e n t i a l l y .Th r o u g hNMR c h a r a c t e r i z a t i o n , t h es t e r e o me t r i cr a t i oo ft h ep r o d uc t sc o u l db ed e t e r mi n e d.

Ov e r a l lRe a c t i on:

C10 H 18 O + HOCl + C H 3 COONa 

C10 H 16 O + −¿ CO O ¿

+¿ ¿ H3O

+ NaCl + C H 3

I nt h eo x i d a t i o n r e d u c t i o nr e a c t i o ns ho wna b o v e , t hes t a r t i n gma t e r i a l , ( 1 S) ( ) b o r n e o li s o x i d i z e du s i n gh y po c h l o r o usa c i dt oc a mp h o r .Af t e rt h i so xi d a t i o n , s o d i u mb or o h yd r i d ea c t sa s t h er e du c i n gr e a g e ntt or e d u c ec a mp h o r ,f o r mi n g( 1 S) ( ) b o r n e o la n d( 1 S) ( +) i s o b o r n e ol . I n g e n e r a l , du r i n ga no x i d a t i o nr e d u c t i o n( r e d o x )r e a c t i o n, t h e r ei sa c t i vi t yb e t we e ne l e c t r on swh i c h c a u s e sac h a n g ei nt h eo x i d a t i onnu mb e r so ft h ec omp o un d si n v o l v e d .Si n c ee n ou g hp r o du c twa s n o to b t a i n e da tt h ee n do ft h eo x i d a t i o ns e s s i o n , t h er e d u c t i o np o r t i o no ft h i se x p e r i me n twi l lbe u s i n gar a c e mi cmi x t u r eo fc a mp h ora st h es t a r t i n gma t e r i a l .

Re duc t i onMe c ha ni s m: 4C 10 H16 O + NaBH4 + 4H2 O ——> 4C 10 H 18 O + NaB(OH) 4

I nt h i se xp e r i me n t , t h er e d u c t i o np o r t i o no ft h er e d o xr e a c t i o nwa se x a mi n e d. Du r i n gt h i s p r o c e s s ,t h eo p t i c a l l ya c t i v es t a r t i n gma t e r i a l , c a mp h o r , i st r a n s f o r me db a c ki n t oas e c o n d a r y a l c oh o l . Th i sr e d u c t i v et r a n s f o r ma t i o ni sa c c omp l i s h e du s i n gs o d i u mb o r o h y d r i d e , Na B H4 , a s t h er e du c i n ga g e n t . On c eme t h a n o l , s o d i u m bo r o h yd r i d ea n dc a mp h o ra r ec o mb i n e di nas o l u t i o n a nb e g i nt ot a k ea c t i o n .Si n c e o v e rh e a tf o raf e wmi n u t e s ,wa t e ri sa d de d . Af t e rt h i s ,Na B H4 c o n emo l a re q u i v a l e n to fs o di u mb o r o h y d r i dec a nr e a c twi t hf o u rmo l a re q u i v a l e n t so fc a mph o r , e a c hf o u rh yd r i d ei o nsf r o m Na B H4 H4

c a nr e a c twi t hc a mp h o r .Ea c hh y d r i d ei o nf r o m Na B

wi l la t t a c kt h ee l e c t r o p h i l i cc a r b o no ft h ec a r b o n y lo nc a mp h o ra tC2 ,e i t h e ri nt h ee n d o -

o re x o -r o u t e . Be c a u s et h e r ea r emu l t i pl ea t t a c kr out e sf o rt h eh y d r i d ei o nt ot a k e , ami x t u r eo f d i a s t e r e o me r si sp o s s i b l ef r o mt h er e a c t i o n . Aswi t hmo s t r e a c t i o n st h a tf o r md i a s t e r e o me r s , o n e c o mp o u ndi sp r e f e r e nt i a l l yf o r me do v e rt heo t h e r . Noma t t e rwh i c hwa yt h eh y d r i dei o np r o c e e d s , t h ec h i r a lc e nt e ra tC2o nc a mp h o ri sr e e s t a b l i s h e d . I ft h ee n doa t t a c kt a k e sp l a c e ,( 1 S) ( ) b o r n e o li sf or me d;c o ns e q u e n t l y ,i ft h ee x oa t t a c ko c c u r s , ( 1 S) ( +) i s ob o r n e o li so bt a i n e d . Th e d i a s t e r e o s e l e c t i v i t yo ft h er e d u c t i o nr e a c t i o nc a nbeq ua n t i fie du s i n g❑1 H

NMRs p e c t r o s c o p y .

St oi c hi ome t r yTa bl e :

Co mpound c a mph or me t ha nol

For mul a C10 H 16 O CH 3 OH

Amount Us e d

MW (

0 . 10 06g 0. 5mL

152 . 23 32. 04

mol

mmol

Mol ar Equi v s

Ot he r

0. 0006608 0. 01235

0 . 6608 1 2. 35

4. 0 e x c e s s

de ns i t y 0. 792

g ) mol

g cm3

s od i um Na B H4 bo r oh y dr i de

0. 053g

37. 83

0. 001404

1 . 401

1. 0

-

di e t h y le t h e r (C2 H 5 ¿ 2 O

4. 0mL

74. 12

0. 03848

3 8. 48

e x c e s s

de ns i t y 0. 713 g cm3

wa t e r

H2 O

3. 5mL

18. 015

0. 1936

193 . 6

4. 0

de ns i t y 0. 997 g cm3

Li mi t i ngRe a g e nt :c a mp h or The o r e t i c a lYi e l do f( 1 S) ( ) bor ne oland( 1 S) ( +) i s o bo r ne o l :0 . 1 0 1 9g

Pr e c a ut i ons : 

Na B H4



Me t h a n o li st o x i ct ot h eo p t i cn e r v e , we a rg o g g l e s .

i safla mma bl es o l i da ndg e n e r a t e sh e a t wh e nwe t .

Pr oc e dur e

Obs e r v at i ons

1.Yo uwi l ln e e d( i no r d e r ) : i c eb a t h , 2 5o r5 0mLr o u n d b o t t o mfla s k ,s t i rr od , g r a d u a t e d c y l i nd e r s , p i p e t s , s a n db a t h , h o t p l a t e , c l a mp s ,Hi r s c hf u n n e l , v a c u um fil t r a t i o ns e t up( t u b ea n d fil t r a t i o np a p e r ) , 1 0mL Er l e nme y e rfla s k,s o d i u ms u l f a t e d r y i n ga g e n t ,fil t e rp i p e t( c o t t o n ) , t a r e d5 0mLs i d e a r mfla s k , b o i l i n gc h i p s , l a r g eb e a k e r , t h e r mo me t e ra n da d a p t e r , a s p i r a t o r o rr o t o v a p ,s e a l e dc a p i l l a r yt u b e a n dNMRa n a l y s i sma t e r i a l s 2.Re c o r dwe i g h to fa mo u n to f We i gh t :0 . 1 0 0 6gc a mp h o r c a mph o rb e i n gus e d o r1 0 0 . 6mgc a mp h o r 3.Ba s e do nt h ema s so ft h ec a mp h o r , Ca mp ho ru s e d :1 0 0 . 6mg fig u r eo u tt h ea mou n to fr e d uc i n g n ds o l v e n t a g e n t( Na B H 4 )a Amo u ntofme t h a n o ln e e d e d :0 . 5mL t h a no lu s e d :0 . 5mL ( me t h a n o l )t h a twi l l b en e e d e di n Me t h er e d u c t i o np r oc e s s : 8 7 f g 1 j kl u ntofNa B H4 n e e de d :5 0mg Us e0 . 5mLme t ha n olf o r Amo e v e r y1 00mgo fc a mp ho r s e d :53mg Na B H4 u Us e5 0mgNa B H4 f o r e v e r y1 00mgo fc a mp ho r 4.Ad dt h ec a l c u l a t e da mo u n tof me t h a n o lt ot h efla s kc o nt a i n i n g t h ec a mp ho ra n ds t i ri t wi t hag l a s s r o du n t i l t hec a mp h o rd i s s o l v e s . 5.Pr e p a r ea ni c eb a t ha n das a n d b a t h . 6.Sl o wl ya d di nt h eNa B H4 t o Na B H 4 fiz z e dwhe ni t wa ss l o wl ya d d e d . t h ec a mp ho rs o l u t i o n . I fne c e s s a r y , He a twa sg e n e r a t e dd u r i n gt h i sr e a c t i o na n d c o o lt h es o l u t i oni nt h ei c eb a t ht o s l i gh tc o o l i n gwi t ht h ei c eb a t hwa sn e e de d . k e e pi ta tr o o mt e mp e r a t u r ef o rt he a d d i t i o np r o c e s s .

7.Onc et h eNa B H4 h a sb e e n Th es o l u t i o nwa sac l e a r , wa t e r l i k el i q u i d wi t hapu n g e n to d o r . a d d e d, b o i lt hes o l ut i o nf o r2 3 mi n u t e s . Al lo ft h eNa B H4 s h o u l db ed i s s o l v e d . 8.Al l o wt h es o l u t i ont oc o o la n d Amo u ntofwa t e rus e d:3. 5mL me a s u r eo ut3. 5mLo fi c ewa t e r f o re v e r y1 00mgo fc a mph o ru s e d . 9.Af t e r2 3mi n u t e sh a sp a s s e da n d Wh i t es o l i dp r e c i p i t a t e dwi t ha d d i t i o no fi c e t h er e a c t i o nh a sc o o l e ds l i g h t l y , wa t e r . a d dt hei c ewa t e rwi t hap i p e t . 10 . Col l e c tt h es o l i df o r me db y Th er e a c t i o nv e s s e lwa sr i n s e dwi t hwa t e r v a c u um fil t r a t i o nwi t haHi r s c h s e v e r a lmo r et i me st oo b t a i na l l p r o d u c ts t u c k f u nn e l , t ofla s k . 11 . Le tt h es o l i dd r yont h ev a c u um.

Th epr o d uc td r i e df ora na d d i t i o n5 6mi n u t e s o nv a c u u m.

12 . Pl a c et h ed r ys o l i di n t oa1 0mL Er l e nme y e rfla s k. Amo u ntofe t h e ru s e d :4 . 0mL 13 . Di s s o l v et h es o l i di nami ni ma l a mo u n to fdi e t h y le t h e r : Us e4 . 0mLe t h e rf o re v e r y 1 0 0mgofc a mp h o ru s e d 14 . Dr yt h ee t h e rs o l u t i o nwi t hs o d i u m s u l f a t eu n t i lt h es ol u t i o ni s t r a n s p a r e n ta n dt h es o d i u ms u l f a t e n ol o n g e rc l u mp s . 15 . We i g ha5 0mLs i d e a r me dfla s k We i g h to ffla s k :4 8. 3 7 1g wi t haf e wb o i l i n gc h i p s 16 . Fi l t e rt hes o l u t i o ni n t ot h es i d e a r me dfla s ku s i n gafil t e rp i p e t . 17 . Se tu pawa r m wa t e rb a t hwi t ha n e x t e r n a lt h e r mo me t e rt o 4 5+/ -5 C 18 . Cl a mpt h efil t r a t i o nfla s ki nt h e wa r m wa t e rb a t hwhi l e ma i n t a i n i n gt h et e mp e r a t u r e . Ev a p o r a t et h ee t h e ru s i n ga n a s pi r a t o ro rar o t o v a p. Wh e na s ma l la mou nto fe t h e ri sl e f t , r e mo v et h ewa t e rb a t ha n dfin i s h wi t ha na s p i r a t o r .

19 . We i g ht h ep r o d u c t i nt h efla s ka n dWe i g h to ffla s kwi t hp r o d u c t :4 8 . 41 7g c o mp a r ei tt ot het a r e dfla s kwi g ht . De t e r mi n et hep e r c e n ty i e l df r o m Pe r c e n tYi e l d :4 5 . 1 4 % t h er e a c t i o n . 20 . De t e r mi n et heme l t i n gp o i n to ft h e Me l t i n gPo i n t :2 0 4. 6 20 5 . 9C p r od u c tu s i n gas e a l e dc a p i l l a r y t u b e . p e c t r o s c o p y ( s p e c t r u ma t t a c h e db e l o w) 21 . Ge ta n ❑1 H NMRs s c a no ft hep r o d u c t t oa n a l y z et h e d i a s t e r e o me r i cr a t i o.

Re s ul t s : Co mpound

Amo unt Us e d/ Obt a i ne d

mo l

The o r e t i c a l Yi e l d

% Yi e l d

mp( C)

c a mp h o r

0 . 10 0 6g

-

-

1 7 5 1 77

( 1 S) ( ) b o r n e o la nd ( 1 S) ( +) i s o bo r n e o l

0 . 0 46g

0 . 0 0 0 66 0 8 ( 0 . 6 6 0 8mmol ) 0 . 0 00 2 9 8 2 ( 0 . 2 9 8 2mmol )

0. 1 0 19g

4 5 . 14 %

2 04 . 6 2 0 5 . 9

Fi gur e1. 1NMRs pe c t r os c op ys c a nofbo r ne ol , oneoft wodi a s t e r e ome rpr od uc t s .

Fi gur e1. 2NMRs pe c t r os c op ys c a nofi s ob or ne ol , oneoft wodi a s t e r e ome r pr o duc t s .

Di s c us s i on : Th efir s tha l fo ft heo v e r a l l r e a c t i on , t h eo x i d a t i ono fb o r n e o lt oc a mp h o r , wa s a c c o mpl i s h e du s i n gh y po c h l or o u sa c i d. Thi so x i d a t i ont ur n e dt h ec h i r a ls e c o n d a r ya l c o h o l , b o r n e o l , i nt oak e t o newi t ha ne l e c t r o p h i l i cc a r b on y l ,c a mp h o r . Th ec a mph o ro b t a i n e df r o mt h e o x i d a t i o np r o c e s swa sf ur t h e rr e d u c e di nt h i ss e s s i o nu s i n gs o d i u m bo r o h yd r i d e . Ca mp h or , t h es t a r t i n gma t e r i a loft h ea b o v er e d u c t i o nr e a c t i o n , i sac y c l i cmo n o t e r p e n e k e t o n et h a ta p pe a r sa sawh i t eorc o l o r l e s sc r y s t a l l i n ep o wd e rwi t hap u n g e n to d or . Ca mp h o rc a n b ee x t r a c t e df r o mmul t i p l et r e e s , i tc a nb ec h e mi c a l l ys y n t h e s i z e di nal a bo rb i o s y n t h e t i c a l l yi n l i v i n go r g a n i s ms . I na d d i t i o n ,i th a sme d i c i n a l u s e sa l o n gwi t hi nd u s t r i a lp r o d u c t i o no fma t e r i a l s . De p e n di n go nt her e a g e n tu s e d , c a mp h orc a na l s obeu s e dt os y n t h e s i z eav a r i e t yo fo t h e r c o mp o u nd s . I nt h er e d uc t i o ns e s s i o na bo v e , ar a c e mi cmi x t u r eo fc a mp h o rwa sc o mb i n e dwi t h me t h a n o la n ds o di u mb o r o h y d r i d eo v e rhe a t .On c et h er e a c t i o nc o o l e d ,i c ewa t e rwa sa d d e dt o t h es o l u t i o nt op r o du c ewh i t es o l i dl u mp so fp r o d u c t . Ast h es o d i u mb o r o h y d r i dea c t e dt or e d uc e t h ec a mp h o r , t h eh y d r i d e sa t t a c k e dd i ffe r e n t l yt op r od u c et wod i a s t e r e o me r s , ( 1 S) ( ) bo r n e o la n d ( 1 S) ( +) i s o bo r n e ol . Si n c eo n eo ft h e s ec o mp ou n d sf o r me dp r e f e r e n t i a l l y , ❑1 H

NMR

s p e c t r o s c o p ywa su s e dt od e t e r mi n et h ed i a s t e r e ome r i cr a t i o . Ass e e na bo v ei nFi g u r e1 . 1 ,b o r n e o l ’ sh y d r o g e np e a k sa t4 . 0p p ma ndh a sas ma l l e ra r e a . I nc o mp a r i s o nt ob o r ne o l , i nFi g u r e1 . 2 , i s o b o r n e o l ’ sh y d r o g e np e a k sa t3. 6a n dh a sa na r e a n e a r l yt h r e et i me sl a r g e r .Du et ot hi so b s e r v e dr e l a t i o n s h i p , i twa sde t e r mi n e dt h a ti s o b o r n e o l , t h e e x o a t t a c kp r o d uc t , wa sf o r me df a v o r a b l yc omp a r e dt ob o r n e o l . Th e( 1 S) ( +) i s o b o r n e o lf o r m wa sf a v o r e dd u et ot h epr e f e r e n c eoft h ea n i o nt oa v o i ds t e r i ch i n d r a nc eoft h ed i me t h y lg r o upo f c a mp h orwh e na t t a c ki n g . Th et h e o r e t i c a ly i e l dwa sc a l c u l a t e db yo b s e r v i n gt hemo l a re q u i v a l e n t so fc a mp h ora n d b o r n e o li nt h er e a c t i o n ,kn o wi n gt ha tc a mp h o ri st h el i mi t i n gr e a g e n t . Ba s e do nt h ea mo u ntof c a mp h oru s e da ss t a r t i n gma t e r i a l , i t wa sd e t e r mi n e dt h a t0 . 10 1 9g r a mso fb o r n e o l / i s o b or n e o l p r o d uc ts h o u l db ep r o d u c e df r o mt h er e a c t i o nt h e o r e t i c a l l y . Ast h er e a c t i o nwa sc o mp l e t e d ,o nl y 0 . 0 46g r a msofp r o d u c to b t a i n e d , g i v i n ga4 5. 1 4 %y i e l d .

I na d d i t i o nt ot a ki n ga n ❑1 H

NMRs p e c t r os c op ys c a no ft h ep r o d u c t , ame l t i n gp o i n t

wa sa l s oo b t a i n e d . Du r i n gt h ec o u r s eo ft h ea b o v er e a c t i o n , t h eme l t i n gp o i n to ft h ep r o d u c twa s 2 0 4 . 6 2 0 5. 9C.Wh i l et h eme l t i n gp o i ntofb o r n e o li s2 0 62 0 8C, i s o b o r n e o li ss l i g h t l yh i g h e ra t 2 1 4C. I nc o n t r a s t , c a mph o r , t h es t a r t i n gma t e r i a l ,h a same l t i n gp oi n to f1 75 1 7 7 C. Th eme l t i n g p o i n to bt a i n e df r o mt h ep r o d u c t i ss l i g h t l yl o we rt h a nt h a t o fb o r ne o l , a n dde c e n t l yh i g h e rt ha n c a mp h or . Al t h ou g ht h eme l t i n gp o i n ts ho u l db eh i g h e r ,i ti si nt h eg e n e r a lr a n g eo ft h ed e s i r e d p r o d uc t ;h o we v e r ,i tmo s tl i k e l yh o l d si mp u r i t i e s .Fo re xa mp l e , s omes t a r t i n gma t e r i a lma ys t i l lb e p r e s e n ti nt h efin a lp r o d u c t , l o we r i n gt heme l t i n gpo i n ts i g n i fic a n t l y .

Ca l c ul a t i ons :  a mou ntofpr odu c tobt a i ne d: 48. 417g–48. 371g=0. 046g  mol / mmolo fpr o duc t : 0.046 g g 154.25 mol

=0. 0002982molx1000=0. 2982mmol

 mol / mmolo fc a mphor( l i mi t i n gr e a g e nt ) : 0.1006 g g 152.23 mol

=0. 0006608molx1000=0. 6608mmol

 mol / mmolo fNa B H4 : 0.053 g g 37.83 mol

=0. 001401molx1000=1. 401mmol

 mol / mmolo fdi e t h y le t he r : 4.0 mL x 0.713 74.12

g mol

g cm 3

=0. 03848molx1000=38. 48mmol

 mol / mmolo fwa t e r :

3.5 mL x 0.997

g cm3

g 18.015 mol

=0. 1936molx1000=193. 6mmol

 t he or e t i c a lyi e l d: 0. 0006608moll i mi t i n gr e a g e ntx154. 25

 pe r c e ntyi e l d 0.046 g 0.1019 g

x100% =45. 14 %

g pr o duc t=0. 101 9gpr odu c t mol

Re duc t i onPos tLa b 1. To what do the (+) and (-) notations in the trivial names of the borneol and camphor refer? Be thorough in your explanation. 



Used to name enantiomers. An enantiomer that rotates light to the right are called (+) or dextrorotary (D). Enantiomers that rotate light to the left are called (-) or levorotary (L). (+) and (-) enantiomers have different properties

2. We will determine the ratio of borneol to isoborneol formed by the reduction of camphor using 1H NMR. In borneol, the exo hydrogen on the ring carbon bearing the hydroxyl group appears at 4.0 ppm, whereas the analogous hydrogen in isoborneol appears at 3.6 ppm. Suppose you isolate 0.264 g of product, and integration of the key hydrogen signals yield these values: H at 4.0 ppm: 1.00 H at 3.6 ppm: 3.14 a. How many moles of borneol/isoborneol mixture was formed? 0.264 g g 154.25 mol

= 0.00171 mol

b. What percentage of the mixture is borneol? What percentage is isoborneol? bo r n e o l

1.0 4.14

i s o b o r n e ol

x100=24. 2%

3.14 4.14

x100=75. 8

c .Ho wma n ymo l e so fb o r ne o lwe r ef o r me d ?Ho wma n yofi s o b o r ne o l ? molbo r n e o l 0 . 2 42x0 . 0 0 1 7 1=0 . 0 0 0 4 14mo lo r0 . 4 1 4mmo l moli s o b o r n e ol 0 . 7 5 8x0 . 00 1 7 1=0 . 0 0 1 2 9mo lo r1 . 2 9mmol

3 .So d i u m bo r o h yd r i d ei sap o we r f u lr e d u c i n ga g e nt . Th er e du c t i o np r o c e s si sh i gh l y e x o t h e r mi c . Asar e s u l t , t h epr o c e du r ec o nt a i n s3p r e c a ut i o n a r ys t e p s . Li s t t h et h r e ea n d t e l lmewh yt h e yh e l p e dt h er e a c t i o n/ wo r k u pf r o mg e t t i n go u to fh a n d?  u s i n ga ni c eb a t h  a d di n gs o d i u mb o r o h y d r i d ev e r ys l o wl y  a d di n gi ti ns ma l lp o r t i o ns Th er e a c t i o ng e n e r a t e sh e a t a n da l lo ft h e s ep r e c a ut i o n she l pl o we rt h er a t ea twh i c ht h e r e a c t i onh e a t st h ev e s s e l 4 .Wh yc o ul d n ’ t y o uu s eI Ri n s t e a dofNMRt od e t e r mi net h ed i a s t e r e o s e l e c t i v i t yo ft h i s r e a c t i on ?Ca ny o ut h i n ko fa n o t h e ri n s t r u me n t a lme t h o dwh i c hmi gh tb ea p p r o p r i a t ef o r q u a n t i t a t i n gd i a s t e r e o me r i cd i s t r i b ut i on s ? AnI Rs p e c t r u mc o u l dn o ts e pa r a t eb o t hi s o me r s . Apo l a r i me t e rwo u l da l s ob eu s e f u lt o de t e c tt h eo p t i c a lr o t a t i o nd i ffe r e n c e sb e t we e nt hec o mp o u n d s . 5 .Su p p os ey o un e e dt os u pp l e me n ty o ur1 Sc a mp ho rwi t hr a c e mi cc a mp h orf o rt h e r e d u c t i o ne x p e r i me nt . Wi l l t h i sa ffe c tt h eou t c o meoft hee x p e r i me n t ?Wi l l i ta ffe c tt h e NMRr e s u l t s ?Exp l a i n . No , b e c a u s eo ft h ee n d o -a n de x o -a t t a c k sofc a mp horb yt h eh y d r i d ei o n , bo t h di a s t e r e ome r swo u l db ep r od u c e da n y wa y s . 6 .Wh yi si ti mp o r t a n tt oob t a i nt heMPoft h ec a mp hori nas e a l e dc a p i l l a r yt u b e ? Th es e a l e dc a p i l l a r yt u b ep r e v e n t ss u b l i ma t i o noft h ep r o du c t ....