7/22/2019 Organic Chemistry Lab19.16.13

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MREKOCF FDHJCV\RS C

AKBMRK\MRS

220A-\uh ;-

7/22/2019 Organic Chemistry Lab19.16.13

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Cotrmluftcmo7

\dh purpmsh mi tdh akb, Vmaubcacty \hsts, cs tm lhjmostrkth dmw tdh jmahfuakr

strufturh mi fmjpmuols dks ko cjpkft mo tdhcr prmphrtchs kol tdhrhimrh tdhcr

bhdkvcmr luh tm cothrjmahfuakr imrfhs kol tdh pmakrcty mi tdh ecvho fmjpmuols.

Vmaubcacty, tdh kbcacty mi k fmjpmuol (smauth) tm bh lcssmavhl co k ecvho smavhot,cs lhthrjcohl by tdh strufturh, pmakrcty kol thjphrkturh mi bmtd tdh smauth kol

tdh smavhot. Cotherka tm tdh clhk mi smaubcacty cs tdh kbcacty mi smavhot wctd k sht mi

prmphrtchs, tm lcssmavh mtdhr fmjpmuols tdkt sdkrh scjcakr shts mi prmphrtchs sufd

ks pmakrcty kol tdh cothrjmahfuakr kol cmocf imrfhs kt paky. \dcs fmofhpt, Acnh

lcssmavhs acnh, kaamwhl us tm imrjuakth wmrncoe dypmtdhscs wctd rhekrl tm tdh

lcssmfcktcmo mi fmjpmuols co fhrtkco smavhot. Prhlcftcmos mi smaubcacty whrh

jklh imr 5 fmjpmuols, co hkfd mi tdh tdrhh smavhots, wkthr, htdkoma kol acermco,

uscoe nomwahleh mbtkcohl irmj tdh ahfturhs, ks whaa ksJkfrmsfkah kol

Jcfrmsfkah Mrekocf Hxphrcjhots (pkehs

7/22/2019 Organic Chemistry Lab19.16.13

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FMJPMXOLJU

(e/jma)

Lhoscty

(e/jA)

Yma.

(jA)

Jkss

(e)

jma Dkzkrl

Bhozmcf kfcl

F9D8FMMD;22.;2 e/jmah ;.2983 e/jA - .02 e ;.9< x

Crrctkot (snco hyhs,

codkaktcmo, coehstcmo)

Rhsmrfcoma

F9D9M2;;0.;; e/jmah ;.252 e/jA - .02 e ;.42 x Crrctkot (snco hyhs,

codkaktcmo, coehstcmo)

Bcpdhoya

(F9D8)2

;8

7/22/2019 Organic Chemistry Lab19.16.13

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Hxphrcjhotka7

Ohfhsskry hqucpjhot wks kfqucrhl (sjkaa thst tubhs, thst tubh stkol, spktuak, bhknhrs, stcr rmls, ) kol k dmt

wkthr bktd stkrthl, jkcotkcocoe k amw bmca, kssujhl tm bh ;00F. Hkfd mi tdrhh sjkaa bhknhrs whrh icaahl wctd

moh mi hkfd, wkthr, acermco, kol htdkoma (tdh tdrhh smavhots). Hkfd mi shvho thst tubhs icaahl wctd .02 erkjs mi

hkfd mi shvho fmjpmuols tm bh thsthl. ;.0 jA mi smavhot wks kllhl tm hkfd mi tdh shvho thst tubhs kol eakss

stcrrcoe rmls whrh ushl tm frusd tdh smauth cotm k imrj jmrh rhklcay lcssmavhl (ci fkpkbah mi lmcoe sm).

Mbshrvktcmos wctd rhsphft tm smaubcacty kt rmmj thjphrkturh whrh rhfmrlhl (Ice. 2). Koy fmjpmuols tdkt whr

cosmaubah kt rmmj thjphrkturh whrh pakfh cotm k dmt wkthr bktd, moh kt k tcjh kol tm lhthrjcoh smaubcacty kt

;00F, kol rhfmrlhl (Ice. 2). \dh kbmvh prmfhlurh wks rhphkthl twm kllctcmoka tcjhs, imr hkfd mi tdh shvho

fmjpmuols wctd tdh tdh twm rhjkcocoe smavhots imr k tmtka mi tdrhh trckas.

Lcsfusscmo7

Fmjpmuol Ukthr Htdkoma Acermco

28F DM\ 28F DM\ 28F DM\

Bhozmcf kfcl Om Om Om Shs Om Shs

Rhsmrfcoma Om Shs Shs Shs Om Om

Bcpdhoya Om Om Om Shs Shs Shs

Vmlcuj bhozmkth Shs Shs Shs Shs Om Om

Vmlcuj suaikth Shs Shs Om Om Om Om

Bhozca Om Om Om Om Shs Shs

Vkacfyacf kfcl Om Shs Pkrtcka Shs Om Om

Iceurh 27 \kbah mi rhsuats imr smaubcacty kt rmmj thjphrkturh kol (kssujhl) ;00F imr 5 fmjpmuols,

co hkfd mi 6 smavhots.

7/22/2019 Organic Chemistry Lab19.16.13

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Ukthr kol htdkoma krh bmtd fmosclhrhl tm bh pmakr prmtcf smavhots. Prmtcf smavhots krh lcstcoeucsdhl irmj

kprmtcf smavhots bhfkush mi tdhcr M-D kol O-D bmols, kol tdus tdhcr kbcacty tm imrj dylrmeho bmols kol

lcssmavh pmakr substkofhs. Pmakr prmtcf smavhots fko kasm shrvh ks k smurfh mi prmtmos, imrjcoe bmols wctd

strmoe oufahmpdcahs (Jksthr Mrekocf Fdhjcstry, 20;6). Ukthr cs by ikr tdh strmoehr fkolclkth imr k pmakr

prmtcf smavhot wctd k lchahftrcf fmostkot mi 40 kol lcpmah jmjhot mi ;.48, mvhr htdkomas 28 kol lcpmah

jmjhot mi ;.93. Fmosclhrhl k jmlhrkthay pmakr smavhot, co kllctcmo tm ct omo pmakr, F-D pmrtcmos, htdkoma

stcaa fmotkcos pmakrczhl MD ermups tdkt kaamw ct tm lcssmavh smjh pmakr fmjpmuols kol tdh fkpkbcacty tm

imrj D-bmols, hsphfckaay wctd tdh kllctcmo mi dhkt. Acermco cs k omopmakr, dylrmfkrbmo smavhot cofkpkbah m

lcssmavcoe koy strcftay pmakr fmjpmuols, hvho wctd kllctcmo mi dhkt. Prhlcftcmos whrh jklh smahay mo tdh

bkscs mi nomwahleh mi pmakrcty kol iurtdhr coimrjktcmo fmofhrocoe prmtcf, kprmtcf kol jmlhrkthay pmakr

smavhots ks whaa ks dylrmfkrbmos wctd pmakr ermups whrh covhstcekthl iurtdhr upmo fmjpahtcmo mi

hxphrcjhotka prmfhlurhs kol rhsuats tdkt lhvckthl sacedtay irmj mrcecoka prhlcftcmos.

Uctd k ihw hxfhptcmos, jmst prhlcftcmos jklh purhay upmo tdh pmakrcty mi k ecvho fmjpmuol whrhfmoscsthot wctd tdh hxphrcjhotka icolcoes. \dhsh cofaulh7 bcpdhoya, bhozca, smlcuj suaikth, kol smlcuj

bhozmokth. Bcpdhoya, k omopmakr dylrmfkrbmo wks prhlcfthl tm lcssmavh moay co acermco bkshl upmo tdhcr

sdkrhl pmakrctchs. Bhozca, kasm k omopmakr fmjpmuol, dhal truh tm tdh mrcecoka prhlcftcmo, moay lcssmavcoe co

acermco. Bmtd smlcuj suaikth kol smlcuj bhozmokth whrh hxphfthl tm lcssmavh co wkthr, kol pmsscbay co

htdkoma luh tm tdh pmakr, cmocf pmrtcmos kttrcbuthl tm tdh prhshofh mi smlcuj> dmwhvhr moay smlcuj

bhozmokth wks kbah tm lcssmavh co htdkoma jmrh tdko acnhay luh tm tdh ikft tdkt smlcuj suaikth cs purhay ko

comrekocf skat uoacnh tdh mrekocf htdkoma kol tdh prhshofh mi jkoy F-D bmols imuol co htdkoma.

Rhsmrfcoma, bhozmcf kfcl, kol skacfyacf kfcl whrh kaa hxphfthl tm bh cosmaubah co wkthr> dmwhvhr moay

bhozmcf kfcl wks fmjpahthay cosmaubah co wkthr (kt koy thjphrkturh), wdcah bmtd rhsmrfcoma kol skacfyacf

kfcl whrh smaubah co wkthr kt ;00F. Rhsmrfcoma kol skacfyacf kfcl whrh fmjpahthay cosmaubah co acermco, ko

fmjpahthay smaubah co htdkoma. Bhozmcf kfcl wks moay kbah tm lcssmavh co acermco kol htdkoma wdho dhkt wk

kppachl. Iurtdhr rhklcoe wks lmoh tm bhtthr uolhrstkol tdh rhsuats mi tdhsh tdrhh fmjpmuols tdkt kaa shhjh

tm dkvh omo pmakr dylrmfkrbmo pmrtcmos wctd kt ahkst 8 fkrbmos, kol kt ahkst moh pmakrczhl iuoftcmoka ermup

co stkrn fmotrkst tm cts omopmakr pmrtcmos. \dh krmjktcf rcoe co bhozmcf kfcl kol cts omopmakr prhshofh wks

ikr jmrh phrsukscvh tdko tdh pmakrczhl fkrbmxyacf kfcl ermup. Kasm tdhrh wks omtdcoe ikvmrcoe tdh

imrjktcmo mi fkrbmxyakth mvhr tdh prhshofh mi tdh fkrbmxyacf. \dcs ahkocoe tm bhcoe jmrh omo pmakr lhspcth

cts iuoftcmoka ermup kaamwhl ct tm bh lcssmavhl co tdh omopmakr smavhot, acermco wdho dhkt wks kppachl.Rhsmrfcoma (kol cts fkrbmxyacf kol kafmdma ermups) kol skacfyacf kfcl (wctd cts 2 kafmdma ermups) whrh pmak

homued tm mvhrfmjh tdh omopmakr dylrmfkrbmo pmrtcmos (krmjktcf rcoe), kol wdho dhkt wks kppachl tm bmt

tdhy whrh kbah tm lcssmavh co tdh vhry pmakr smavhot, wkthr.

7/22/2019 Organic Chemistry Lab19.16.13

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Rhsmurfhs

Jkfrmsfkah kol Jcfrmsfkah Mrekocf Hxphrcjhots, Ucaackjsmo, N.A., 2ol

Hlctcmo. L.F. Dhkatd kol

Fmjpkoy

FdhjUcnc7 \dh Lyokjcf Fdhjcstry \hxtbmmn, Akrsho, Lhajkr. Xocvhrscty mi Fkacimrock, Lkvcs, 20;0

dttp7//fdhjwcnc.uflkvcs.hlu/

Jksthr Mrekocf Fdhjcstry, 20;6

dttp7//www.jksthrmrekocffdhjcstry.fmj/

http://chemwiki.ucdavis.edu/http://chemwiki.ucdavis.edu/http://www.masterorganicchemistry.com/http://www.masterorganicchemistry.com/http://www.masterorganicchemistry.com/http://chemwiki.ucdavis.edu/

7/22/2019 Organic Chemistry Lab19.16.13

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OKJH7 Nktdc Vwkosmo LK\H7 3/;4/;6 AKB VHF\CMO7 \uh

PMV\-AKB [XHV\CMOV

;. Rhpmrt ymur rhsuats co tkbuakr imrj. Vdmw tdh strufturhs mi tdh smacls kol tdh smavhots kol colcfkth tdhsmaubcactys co fmal kol dmt smavhot.

Fmjpmuol Ukthr Htdkoma Acermco

28F DM\ 28F DM\ 28F DM\

Bhozmcf kfcl Om Om Om Shs Om Shs

Rhsmrfcoma Om Shs Shs Shs Om Om

Bcpdhoya Om Om Om Shs Shs Shs

Vmlcuj bhozmkth Shs Shs Shs Shs Om Om

Vmlcuj suaikth Shs Shs Om Om Om Om

Bhozca Om Om Om Om Shs Shs

Vkacfyacf kfcl Om Shs Pkrtcka Shs Om Om

Fmujpmuols7

Bcpdhoya

MDM

Bhozmcf Kfcl

MD

MDRhsmrfcoma

M-

M Ok+

Vmlcuj bhozmkth

M

M

Bhozca

MD

M

MD

Vkacfyacf kfcl

Ok2VM dmwhvhr moay smlcuj

bhozmokth wks kbah tm lcssmavh co htdkoma jmrh tdko acnhay luh tm tdh ikft tdkt smlcuj suaikth cs purhay ko

comrekocf skat uoacnh tdh mrekocf htdkoma kol tdh prhshofh mi jkoy F-D bmols imuol co htdkoma.

Rhsmrfcoma, bhozmcf kfcl, kol skacfyacf kfcl whrh kaa hxphfthl tm bh cosmaubah co wkthr> dmwhvhr moay

bhozmcf kfcl wks fmjpahthay cosmaubah co wkthr (kt koy thjphrkturh), wdcah bmtd rhsmrfcoma kol skacfyacf

kfcl whrh smaubah co wkthr kt ;00F. Rhsmrfcoma kol skacfyacf kfcl whrh fmjpahthay cosmaubah co acermco, ko

fmjpahthay smaubah co htdkoma. Bhozmcf kfcl wks moay kbah tm lcssmavh co acermco kol htdkoma wdho dhkt wkkppachl. Iurtdhr rhklcoe wks lmoh tm bhtthr uolhrstkol tdh rhsuats mi tdhsh tdrhh fmjpmuols tdkt kaa shhjh

tm dkvh omo pmakr dylrmfkrbmo pmrtcmos wctd kt ahkst 8 fkrbmos, kol kt ahkst moh pmakrczhl iuoftcmoka ermup

co stkrn fmotrkst tm cts omopmakr pmrtcmos. \dh krmjktcf rcoe co bhozmcf kfcl kol cts omopmakr prhshofh wks

ikr jmrh phrsukscvh tdko tdh pmakrczhl fkrbmxyacf kfcl ermup. Kasm tdhrh wks omtdcoe ikvmrcoe tdh

imrjktcmo mi fkrbmxyakth mvhr tdh prhshofh mi tdh fkrbmxyacf. \dcs ahkocoe tm bhcoe jmrh omo pmakr lhspcth

cts iuoftcmoka ermup kaamwhl ct tm bh lcssmavhl co tdh omopmakr smavhot, acermco wdho dhkt wks kppachl.

Rhsmrfcoma (kol cts fkrbmxyacf kol kafmdma ermups) kol skacfyacf kfcl (wctd cts 2 kafmdma ermups) whrh pmak

homued tm mvhrfmjh tdh omopmakr dylrmfkrbmo pmrtcmos (krmjktcf rcoe), kol wdho dhkt wks kppachl tm bmt

tdhy whrh kbah tm lcssmavh co tdh vhry pmakr smavhot, wkthr.