ORGANIC CHEMISTRY LECTURE REMOTE HOMEWORK PDF

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Organic chemistry lecture notes and answers for laboratory in person answers...

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Ox i d a t i o no fBo r n e o lt oCa mph o r

Ma r j or i eAr i a s TA: Be nEd u f u l La bPa r t n e r : Ca t h e r i n eSmi t h CHM 2 2 1 1L 0 7 / 1 3 / 2 0 1 3

I nt r o duc t i o n Ano x i d a t i o nr e a c t i o ni n v o l v e st h el o s so fe l e c t r o n s , t h eg a i no fo x y g e no rt h ei n c r e a s ei n o x i d a t i o ns t a t e( He l me ns t i n en . d . ) . Th ea i mo ft h i se x p e r i me n ti st ope r f o r ma no x i d a t i o nr e a c t i o n i n v o l v i n gt h ei n t e r c o n v e r s i o no fb o r n e o lt oc a mp h o ru s i n gc h r o mi ca c i d . Ch r o mi ca c i d( H2Cr O4) i sac o mmo nl yu s e do x i d a n tt h a ti sp r e p a r e da n dh a sa no x i d a t i o ns t a t eof6 +( So l o mo n , 2 0 1 2 ) . Ot h e rpo p u l a ro x i d a nt sa r es o d i u mh y p oc h l o r i t e , h a l o g e n s ,a n de n z y me s . T woi mp o r t a n tc h a r a c t e r i s t i c sofo x i d a t i o nr e a c t i o nsa r e( 1 )i na n yo x i d a t i o nr e a c t i o nar e c i p r o c a l r e du c t i o no c c u r sa n d( 2 )a na t o mo re l e c t r o ng o e sf r omo neu n i t o fma t t e rt oa n o t h e r ( En c y c l o p e d i aBr i t a nn i c an . d ) .Ane x a mp l eo ft h i si sh y d r o g e na t omsb e i n gt r a n s f e r r e df r o m h y d r a z i n et oo x y g e n: N2H4+O2 N2+2 H2O Wh e r eh y d r a z i n e ,l o s i n gh yd r o g e n , i so x i d i z e dt on i t r o g e nwh i l eo x y g e n , g a i n i n gh y dr o g e n ,i s b e i n gr e d u c e dt owa t e r . Tobea b l et of o r mc he mi c a lb o n d s , a t o msdo n a t e , r e c e i v e , o rs h a r ee l e c t r o n s , wh i c hma k e si t p o s s i b l et oa s s i g na no x i d a t i o nn u mb e rt ov e r ya t om. Th eo x i da t i o nn u mb e rs p e c i fie st h en u mb e r o fi t se l e c t r o n st h a tc a nb eu s e dt of or mbo n d swi t ho t h e ra t o msa n dma k emo l e c u l e s ( En c y c l o p e d i aBr i t a nn i c an . d ) . I nt h i se x p e r i me n tas e c o n d a r ya l c o h o l ,b o r n e o l , i so x i d i z e dt oak e t o n e , c a mph o r , u s i n g c h r o mi u mo x i d ea n dd i l u t e dH2SO4. Th e r ei sapo s s i b l es i d er e a c t i o nt h a tma yoc c u ri fr e a c t i o ni s n o td o n e10 0 %c o r r e c t l y . Th eme c h a n i s ma ndt h es i d er e a c t i o nf o rt h i sr e a c t i o ni ss h o wnb e l o w.

Me c h a n i s m:

Si d eRe a c t i o n :

Ex pe r i me nt a l 5mLc o n i c a lv i a l -

0 . 1 8gb o r n e o l

-

1mLe t he ra n ds p i nv a n e

-

Co o l t o0° C

-

1mLa q u e o u ss o l u t i o n8 % Cr O3a n d5 % H2SO4

-

TLC, 1 0 % Et OAc / He x a n e -

Sh a k e1 0mi n u t e s

-

I fbo r ne o ls t i l lp r e s e n t , s h a k ef o r1 0mo r emi n u t e sa ndt h e nh e a ta t5 0° C

Re a c t i o n -

2mLo fCH2Cl 2

-

Tr a n s f e ro r g a n i cl a y e r , wa s ha q ue o u sl a y e rwi t hCH2Cl n dc o l l e c tmo r e 2a l a y e r

-

1mLs a t . Na HCO3

-

St a ndf o r1 0mi n u t e s , d i s c a r da q u e o u sp h a s e

-

Wa s hwi t hs a t . Na HSO3, 1mLH2O,d i s c a r da q u e o u sl a y e r -

-

Dr ywi t hNa O4u s i n g1 0mLc o n i c a lfla s k 2S

Ev a p o r a t es o l v e n ti nh o odo rv a c u um

Pr o d u c t . ( De t e r mi n eTLC, I R, MP , a n d% y i e l d )

or g a n i c

Ta bl eo fChe mi c a l s Che mi c a lNa me

Mol a rMas s

De ns i t y

Me l t i ng

Bo i l i ngPo i nt

Po i nt 2 08° C

2 1 3° C

0. 99g/ c m

1 7 5–1 7 7° C

2 0 4° C

9 8 . 0 7 9g / mo l

1 . 8 4g / c m3

10° C

33 7° C

Et OAc

8 8 . 1 1g / mo l

0 . 8 9 7g / c m3

8 3 . 6° C

77 . 1° C

Di c h l o r o me t h a ne

8 4 . 9 3g/ mo l

1 . 3 3g / c m3

9 6 . 7° C

3 9 . 6° C

Bor n e ol

1 5 4 . 2 5g / mo l 1 . 0 1 1g / c m3

Ca mp h or

1 5 2 . 2 3g / mo l

Sul f u r i cAc i d

So d i u mBi c a r b o na t e

So di u mBi s ul fit e

8 4 . 0 1g / mol

1 0 4. 06g/ mo l

2 . 2 0g / c m3

3 1 . 4 8g / c m

50° C

N/ A

1 5 0° C

N/ A

Sod i ums u l f a t e

1 4 2 . 0 4g / mo l

2 . 6 6g / c m3

8 8 4° C

1 4 2 9° C

Ch r o mi u mt r i o xi d e

9 9 . 9 9g / mo l

2 . 7 0g / c m3

1 9 7° C

25 1° C

Cr O3

Re s ul t s Di s c us s i o n Co nc l us i o n Many oxidation-reduction reactions are as common and familiar as fire, the rusting and dissolution of metals, the browning of fruit, and respiration and photosynthesis—basic life functions. Comprehensive definitions of oxidation and reduction have been made possible by modern molecular structure theory.

Re f e r e nc e

En c y c l o p e d i aBr i t a n n i c an . d . . Ox i d a t i on r e c u t i o nr e a c t i o n( c h e mi c a lr e ac t i o n ) .[ o n l i n e ] Av a i l a b l ea t : h t t p : / / www. b r i t a n n i c a . c om/ EBc h e c k e d / t o pi c / 4 3 6 63 6 / o xi d a t i o n r e du c t i o n r e a c t i o n He l me n s t i n e , A. n . d . . Ox i d at i o nRe du c t i o nRe a c t i o n s–Re d o xRe a c t i o n s . [ o n l i n e ]Av a i l a b l ea t : ht t p : / / c h e mi s t r y . a b o u t . c o m/ o d / c h e mi c a l r e a c t i o n s / a / o x i d a t i o n r e du c t i o n r e a c t i o n s . h t m Sol o mon , W. ( 20 1 2 ) . Ex p e r i me n t a lo r g a n i cc h e mi s t r yl a b o r a t o r yma n u a l . ( Fa l l 2 01 2 / Sp r i n g2 0 1 3/ Summe r2 0 13e d . ) . Ma s o n ,Oh i o :Ce n a g eLe a r n i n g . p . 82 8 6...