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Stereochemistry

Ha Lp Th

HA HC LP TH

2005 Ha Hc Vit NamAll Rights Reserved

Stereochemistry

Hy click vo y xem tip ti liu

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Stereochemistry

Ha Lp Th

Xin chn thnh cm n anh Phm NgcBa (HSP H Ni),anh L Kiu Hng(HSP Vinh), anh Water(Hi Phng);

nhn xt v ng gp nhng kin qubu cho bn dch ny. Xin chn thnh cm n bn Hunh Th

Tuyt Vn (sinh vin Khoa Xy Dng, HCn Th) gip chng ti thit k cchnh nh dng gif tht sinh ng.

Acknowledgements

The Young Vietnamese Chemistry Specialists

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Stereochemistry

Ha Lp Th

S sp xp trong khng gian ca cc nhm xungquanh cacbon t din c th thy r qua vic m hnh

ha phn t

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Stereochemistry

Ha Lp Th

hoc biu din bng vic chuyn i cu trc ngngt sang cu trc ba chiu dng cc ng gch ni v

hnh ci nm

CH3

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Stereochemistry

Ha Lp Th

M hnh ha cu trc lp th l mt yu t rt quantrng kim tra mt phng i xng ca cc phn t

CH3

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Stereochemistry

Ha Lp Th

M hnh ha cu trc lp th l mt yu t rt quantrng kim tra mt phng i xng ca cc phn t

CH3

Mt phngi xng

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Stereochemistry

Ha Lp Th

M hnh ha cu trc lp th l mt yu t rt quantrng kim tra mt phng i xng ca cc phn t

Khng c mt phngi xng

CH3

Mt phngi xng

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Stereochemistry

Ha Lp Th

H qu ca hnh t din l mt mt phng khng ixng ni iu ny xy ra khi c bn nhm th khc

nhau nh vi mt tm t din..

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Stereochemistry

Ha Lp Th

H qu ca hnh t din l mt mt phng khng ixng ni iu ny xy ra khi c bn nhm th khc

nhau nh vi mt tm t din..

Khng c mt phngi xng

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Stereochemistry

Ha Lp Th

nh hng mng li ca s khng i xng ny lmpht sinh ra mt phn t mi m khng th chng kht

ln trn phn t ban u gi l nh gng ca n

Mt phng gng

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Stereochemistry

Ha Lp Th

Mt nguyn t cabon c nh vi bn nhm thkhc nhau c gi l cabon bt i xng(chiral

carbon) v mt cp nh gng khng chng kht lnnhau gi l ng phn i nh(enatiomers)

Cp ng phn i nh

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

Khng c

S h i

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

St h i t

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

St h i t

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

St h i t

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

Khng c tmbt i

St h i t

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

Khng c tmbt i

Stereochemistr

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

Stereochemistry

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Stereochemistry

Ha Lp Th

nh du trung tm bt i xng ca cc phn t diy bng vic nh du sao ln cacbon bt i xng

Tm tm bt i s c ng phn lp th

82

82

Stereochemistry

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Stereochemistry

Ha Lp Th

Cc ng phn khng i nh c tnh cht ha hc vtnh cht vt l ging nhau(ngoi tr khi chng tng

tc vi phn t khng i xng khc) chng ch khcl lm quay mt phng nh sng phn cc theo haihng khc nhau, do nhng hp cht khng c

tm i xng thng c gi bng thut ng quanghot

Ngun

Stereochemistry

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Stereochemistry

Ha Lp Th

Mt phng ca nh sng phn cc c thc m t bng vector in v vector t

tng t, vector tng l mt phng thng ng

Stereochemistry

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Stereochemistry

Ha Lp Th

Mt phng ca nh sng phn cc c th c m t bng vectorin v vector t tng t; vector tng l mt phng thng ng

Phn in v phn t chp th khc nhau; vector

tng c thay th

Stereochemistry

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Stereochemistry

Ha Lp Th

Mt phng ca nh sng phn cc c th c m t bng vectorin v vector t tng t; vector tng l mt phng thng ng

Phn in v phn t chp th khc nhau; vector

tng c thay th

Phn in v phn t chp th khc nhau; vector

tng c thay th

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Stereochemistry

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Stereochemistry

Ha Lp Th

phn

Stereochemistry

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Stereochemistry

Ha Lp Th

quay cc ring,

=

Gc quan st c ()

Khong cch l (dm) x nng C(g/mL) =

quay cc ring bng gc quan st c () chia cho tch ca dibung cha mu (l)(tnh bng dm) vi nng (C) tnh bng g/mL

Trong D k hiu di sng nh sng ca n Natri

Ngunsng

B phn cc

Bung cha mu

B phn tch

Gc quan st

Stereochemistry C h h i

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Stereochemistry

Ha Lp Th

Cu hnh ring

Hng m trong mt phnt quang hot quay nh sng

l ring bit cho tng phn tcho trc,nhng khng lin quan ns nh hng ca cc nhmphn t bao quanh tm bt

i

C th l + hay -

Stereochemistry C hnh ring

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Stereochemistry

Ha Lp Th

Cu hnh ring

biu th cu hnh tuyt i,mt h thng danh php

c ra i trong ccnhm xung quanh tm bt ic sp xp theo tnh utin. Nhm c tnh u tinthp nht c t ng

sau mt phng m bn anglm vic trn y, vhng(cng chiu hay ngcchiu kim ng h) ca ccng ni cho cc nhm cn

li c xc nh.

Stereochemistry Cu hnh ring

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Stereochemistry

Ha Lp Th

Cu hnh ring

biu th cu hnh tuyt i,mt h thng danh php

c ra i trong ccnhm xung quanh tm bt ic sp xp theo tnh utin. Nhm c tnh u tinthp nht c t ng

sau mt phng m bn anglm vic trn y, vhng(cng chiu hay ngcchiu kim ng h) ca ccng ni cho cc nhm cn

li c xc nh.S Sinister ngha l tri

Ngc chiu kim ng hl cu hnh S

Stereochemistry Cu hnh ring

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Stereochemistry

Ha Lp Th

Cu hnh ring

biu th cu hnh tuyt i,mt h thng danh php

c ra i trong ccnhm xung quanh tm bt ic sp xp theo tnh utin. Nhm c tnh u tinthp nht c t ng

sau mt phng m bn anglm vic trn y, vhng(cng chiu hay ngcchiu kim ng h) ca ccng ni cho cc nhm cn

li c xc nh.

Stereochemistry Cu hnh ring

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Stereochemistry

Ha Lp Th

Cu hnh ring

biu th cu hnh tuyt i,mt h thng danh php

c ra i trong ccnhm xung quanh tm bt ic sp xp theo tnh utin. Nhm c tnh u tinthp nht c t ng

sau mt phng m bn anglm vic trn y, vhng(cng chiu hay ngcchiu kim ng h) ca ccng ni cho cc nhm cn

li c xc nh. R (rectus ngha l phi)

Cng chiu kim ng hl cu hnh R

Stereochemistry Cu hnh ring

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S e eoc e s y

Ha Lp Th

Cu hnh ring

R (rectus--phi) S (sinister--tri)

Stereochemistry Nhc li qui tc

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y

Ha Lp Th

Nhc li qui tc

Sp xp cc nguyn t nh trc tip vi alken theos nguyn t.

Nu c s rng buc bt k nguyn t no th nhn

n nguyn t th 2 hoc th 3 cho n khi tmc s khc bit vi cc nguyn t khc.m cc lin kt bi xung quanh cng mt nguyn tNu cc nhm c tnh u tin cao nht cng mt

pha ca lin kt i th phn t l ng phn Z, nu

cc nhm th c tnh u tin cao nht nm khc phavi nhau ca lin kt i th phn t l ng phn E.

Cho ng phn Z v E

Stereochemistry Nhc li qui tc

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y

Ha Lp Th

Nhc li qui tc

Cho cu hnh S v R

Sp xp cc nguyn t nh trc tip vi tm cacbonbt i theo s nguyn t.

Nu c s rng buc bt k nguyn t no th nhn

n nguyn t th 2 hoc th 3 cho n khi tmc s khc bit vi cc nguyn t khc.m cc lin kt bi xung quanh cng mt nguyn tQuay nhm c tnh u tin thp nht ra pha sau; nu

mt ng ni ba nhm c tnh u tin cao nht theo

th t gim dn theo chiu quay ca kim ng h thphn t l R, ngc li nu theo th t ngc chiukim ng h th phn t l S

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Stereochemistry

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y

Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Trc ht xc nh tnh u tin

Stereochemistry

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y

Ha Lp Th

C hai nguyn t cacbon ca 2 nhm th nh vinguyn t cacbon bt i do phi xem xt cc

nguyn t nh vi cc nguyn t cacbon ny v spxp li cc nhm

Stereochemistry

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Ha Lp Th

Sau , lt nghing phn t v pha bn, cho nhmc tnh u tin thp nht (nhm cc nguyn t

hydro) ra pha ng sau.

Nhm c tnh u tin thp nht

Stereochemistry

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Ha Lp Th

Sau , lt nghing phn t v pha bn, cho nhmc tnh u tin thp nht (nhm cc nguyn t

hydro) ra pha ng sau.

Nhm c tnh u tin thp nht

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Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

S

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Thp nht

Stereochemistry

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Ha Lp Th

Thp nht

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Stereochemistry

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Ha Lp Th

Thp nht

R

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

R

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Hydro ang hngv pha sau..

Stereochemistry

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Ha Lp Th

StereochemistryHydro khng ch v pha

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Ha Lp Th

Hydro khng ch v phasau nhng chng ta c thquay phn t xung quanhtrc C--Br

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Trong phn t nychng ta cn lt Hydro

ra pha sau..

Stereochemistry

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Ha Lp Th

Chng ta d dng quay phn t xung quanh trc CHsau lt ngc phn t ra pha sau

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Nhm metyl c tnh u tin thpnhtv phn t ng v tr ca n

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sang cngthc chiu Fischer

iu ny c th n gin ha bng cchdng cng thc chiu 2 D thay v biu din cc

phn t dng 3D. Cng thc 2D m chngta s thit lp thng c gi l cng thc

Chiu Fischer.

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

c c cng thc chiu Fischer, v phn t ca bnvi hai lin kt thng ng ang hng v pha bn,sau .

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

c c cng thc chiu Fischer, v phn t ca bnvi hai lin kt thng ng ang hng v pha bn,sau dt mng phn t thnh hnh phng.

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

c c cng thc chiu Fischer, v phn t ca bnvi hai lin kt thng ng ang hng v pha bn,sau dt mng phn t thnh hnh phng.

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

Kt qu l hnh v phng khng cn nguyn t cacbon trung tmm ch l hai ng thng ct nhau n gin. Cng c th hiungm rng v cng thc 2 chiu nh th ny l ni n ha lp thtuyt i v nn xem phng php ny l mt cch ngn gn vtrung tm lp th.

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

Kt qu l hnh v phng khng cn nguyn t cacbon trung tmm ch l hai ng thng ct nhau n gin. Cng c th hiungm rng v cng thc 2 chiu nh th ny l ni n ha lp thtuyt i v nn xem phng php ny l mt cch ngn gn vtrung tm lp th.

Cc nhm thng ngang hng v pha bn

Stereochemistry

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Ha Lp Th

Chuyn i cu trc 3 chiu ca phn t sangcng thc chiu Fischer

Kt qu l hnh v phng khng cn nguyn t cacbon trung tmm ch l hai ng thng ct nhau n gin. Cng c th hiungm rng v cng thc 2 chiu nh th ny l ni n ha lp thtuyt i v nn xem phng php ny l mt cch ngn gn vtrung tm lp th.

Cc nm thng ngang hng v pha bn

Cc nhm nm ngang anghng ra pha sau

Stereochemistry

Ch t th hi Fi h

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Ha Lp Th

Chuyn t cng thc chiu Fischer sang.

Stereochemistry

Ch t th hi Fi h

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Ha Lp Th

Chuyn t cng thc chiu Fischer sang.

n gin v li cu trc biu din tnh cht lp th

Stereochemistry

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Ha Lp Th

Chuyn t cng thc chiu Fischer sang.

Stereochemistry

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Ha Lp Th

Chuyn t cng thc chiu Fischer sang.

Lm ging nh chng ta ni nhng slide trc

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Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t sau:

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t sau:

Trc ht sp xp cc nguyn t

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t sau:

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Xc nh cu hnh tuyt i

V li cu trc phn t dng 3D.

Stereochemistry

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Ha Lp Th

V li cu trc phn t dng 3D.

Stereochemistry

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Ha Lp Th

Xc nh ha lp th.

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Nhm c tnh u tin thp nht bao gi cng

di cng.Bn c th sp xp th t ca cc nhm trongphn t theo tnh u tin trc tip trn cng thcchiu Fischer, v t c th xc nh c cuhnh ca phn t.

Stereochemistry

Xc nh cu hnh tuyt i ca phn t di y

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Sp xp cc nguyn t

Stereochemistry

Xc nh cu hnh tuyt i ca phn t di y

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

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Ha Lp Th

Sp xp cc nhm theo tnh lp th..

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Sp xp cc nguyn t

Stereochemistry

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Ha Lp Th

Stereochemistry

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Ha Lp Th

Sp xp cc nhm theo tnh lp th.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Stereochemistry

X h h h t t i h t d i

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Stereochemistry

X h h h t t i h t d i

7/28/2019 hoa hoc lap the

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Ha Lp Th

Xc nh cu hnh tuyt i ca phn t di y

Vn chng ta gp phi y l nhmc tnh u tin thp nht khng nm dicng hay trn cng trong phn t.

7/28/2019 hoa hoc lap the

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Stereochemistry

Chng ta s thy ngay vn qua mt movie nh sau y.

7/28/2019 hoa hoc lap the

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Ha Lp Th

Chng ta s thy ngay vn qua mt movie nh sau y.

Nh th ny s gipcc bn hnh dungmt cch d dng hn

Stereochemistry

Nhng iu g s xy ra nu bn ch n gin quay cng thc

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nhng iu g s xy ra nu bn ch n gin quay cng thcchiu Fischer?

Stereochemistry

Nhng iu g s xy ra nu bn ch n gin quay cng thc

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nhng iu g s xy ra nu bn ch n gin quay cng thcchiu Fischer?

Stereochemistry

Nhng iu g s xy ra nu bn ch n gin quay cng thc

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nhng iu g s xy ra nu bn ch n gin quay cng thcchiu Fischer?

Stereochemistry

Nhng iu g s xy ra nu bn ch n gin quay cng thc

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Ha Lp Th

g g y g q y gchiu Fischer?

Nhng chng ta bit lphn t cho c cu hnh R

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Vic quay cng thc chiuFischer pht sinh ra mtng phn i nh.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Qui tc vn dng cng thc chiu Fischer

Khng bao gi quay phn t mt gc0

90 iu ny s lm pht

sinh mt ng phn i nh.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Qui tc vn dng cng thc chiu Fischer

Khng bao gi quay phn t mt gcKhng bao gi quay phn t mt gc0

90 iu ny s lm pht

sinh mt ng phn i nh.

Tht ra th vic sp xp li v tr ca cc nhm xung quanh nguynt trung tm trong mt cng thc chiu Fischer c th pht sinh ramt s ng phn i nh. y cng l mt cng c tt cho victhnh lp mi quan h gia cc phn t bt i. N thng cxem l phng php chuyn i.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nu ly cng thc chiu Fischer ca phn t ban u ( cu hnhRR )v hon v bt c 2 nhm bt k trong phn t s pht sinh ra mtcu trc i nh mi.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nu ly cng thc chiu Fischer ca phn t ban u ( cu hnhRR )v hon v bt c 2 nhm bt k trong phn t s pht sinh ra mtcu trc i nh mi.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nu ly cng thc chiu Fischer ca phn t ban u ( cu hnhRR )v hon v bt c 2 nhm bt k trong phn t s pht sinh ra mtcu trc i nh mi.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Nu ly cng thc chiu Fischer ca phn t ban u ( cu hnhRR )v hon v bt c 2 nhm bt k trong phn t s pht sinh ra mtcu trc i nh mi.

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Mt ln hon v pht sinh ra mt ng phn i nh

Hon v

StereochemistryThc hin hon v ln th hai

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Ha Lp Th

Hon v

Ln 1

Honv

lnt

h2

Stereochemistry Thc hin hon v ln th hai

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Ha Lp Th

.hon v ln th 2 a phn t v dng lp th ban u..

Hon v

Ln 1

Hon

vln2

Stereochemistry

Q i t d th hi Fi h

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Ha Lp Th

Qui tc vn dng cng thc chiu Fischer

Khng bao gi quay phn t mt gcKhng bao gi quay phn t mt gc 090 iu ny s lm pht

sinh mt ng phn i nh.

Khi bn hon v cc nhm, ln th nht cho ra mt ng phn inh, ln hon v th 2 a phn t quay v dng lp th ban uln hon v th ba li to ra ng phn i nh.

Bn nn nh rng phng phphon v ch mang tnh hnh thc

iu ny c ngha l n s khng lm thay i bt c mt tnhcht ha hc hay vt l no trong phn t.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

y p y g gv xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

y p y g gv xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

y p y g gv xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

y y g gv xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

H

C

CH3COO-

NH3+

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

H

C

H3C

-OOC NH3+

v xc nh cu hnh tuyt i ca chng.

H

C

CH3

COO

-

NH3+

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer

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Ha Lp Th

H

H3C

-OOC NH3+

v xc nh cu hnh tuyt i ca chng.

H

C

H3C

-OOC NH3+

H

C

CH3

COO

-

NH3+

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer h h h i h

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

H

C

H3C

-OOC NH3+

H

C

CH3

COO

-

NH3+

H

H3C

-OOC NH3+

12

3S

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer h h h t t i h

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Cl

C

CH2

H3C

Br

CH3

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer h h h t t i h

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Cl

C

C

H2

H3C

Br

CH3

Cl

CH3CH2C Br

CH3

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer h h h t t i h

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Cl

C

C

H2

H3C

Br

CH3

Cl

CH3CH2C Br

CH3

Cl

H3CH2C Br

CH3

Stereochemistry

Chuyn cc phn t di y sang cng thc chiu Fischer h h h t t i h

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Ha Lp Th

v xc nh cu hnh tuyt i ca chng.

Cl

C

C

H2

H3C

Br

CH3

Cl

CH3CH2C Br

CH3

Cl

H3CH2C Br

CH3

1

2

3

S

Stereochemistry

Xc nh cu hnh tuyt i ca mi trung tm bt i trongphn t di y

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Ha Lp Th

phn t di y

H3C

H

OH

CH3C2H5

OH

Stereochemistry

Nguyn t carbon pha trn cha nhm th c tnh u tin thp nhtnm pha trn cng ca phn t

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Ha Lp Th

H3C

H

OH

CH3C2H5

OH

nm pha trn cng ca phn t.

Nhng nhm th c tnh u tin thp nht trnnguyn t carbon nm pha di khng v tr m

chng ta mong mun.

13

2R

Stereochemistry

Do chng ta phi thc hin hai ln hon v a nhm c tnhu tin thp nht trn nguyn t carbon nm pha di v ng

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Ha Lp Th

u tin thp nht trn nguyn t carbon nm pha di v ngv tr.

H3C

H

OH

CH3C2H5

OH

H3C

H

OH

CH3

C2H5

HO

R Hon v ln 1

H3C

H

OH

CH3

C2H5HOHon v ln th 2

Stereochemistry

Trong phn t ny, c hai nguyn t carbon, nm trn v nm di

u c cu hnh tuyt i R

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Ha Lp Th

u c cu hnh tuyt i R

H3C

H

OH

CH3C2H5

OH

H3C

H

OH

CH3

C2H5

HO

R Hon v ln 1

H3C

H

OH

CH3

C2H5HOHon v ln th 21

23

R

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Chng ta bt u bng vic chn mt phn t nh cp,v chuyn phn t th hai thnh phn t th nht bng cch

hon v cc nhm, xem xt mi trung tm bt i ring bit.

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu hai hon v (H:CH3 vsau l CH3:OH) do chng ging nhau ( chng ta

k hiu phn ging nhau bng ch i ngha l identical)

i

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu hai hon v (H:CH3 vsau l CH3:OH) do chng ging nhau ( chng ta

k hiu phn ging nhau bng ch i ngha l identical)Nguyn t carbon pha di: yu cu hai hon v (Etyl:CH3

sau l CH3:OH), do chng ging nhau.

Nh vy hai phn t ny ging ht nhau

i

i

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu hai hon v (H:CH3v sau l CH3:OH) do chng c tnh i nh ( chng ta k

hiu tnh i nh bng ch e cngha l enantiomeric)

e

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu mt hon v (H:CH3)do chng c tnh i nh ( chng ta k hiu tnhi nh bng ch e cngha l enantiomeric)

e

Nguyn t carbon pha di: chng mang tnh i nh

Do hai phn t ny lng phn i nh ca nhau

e

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu mt hon v (H:CH3)do chng ging nhau.

i

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu mt hon v (H:CH3)do chng ging nhau.

Nguyn t carbon pha di: yu cu mt hon v (OH:CH3)do chng mang tnh i nh.

e

i

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: yu cu mt hon v (H:CH3)do chng ging nhau.

Nguyn t carbon pha di: yu cu mt hon v (OH:CH3)do chng mang tnh i nh.

e

i

Do hai phn t khng l nhng ng phn i quangca nhau c ngha l chng khng

phi l nhng enatiomer

Stereochemistry

ng phn khng i quang l nhng ng phn lp th m chngkhng l nh gng ca nhau. iu ny c ngha l nhng phn

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Ha Lp Th

khng l nh gng ca nhau. iu ny c ngha l nhng phnt c mt hoc hn mt trung tm lp th l ging nhau, v mt

hoc hn mt trung tm lp th l i nh trong cu hnh ca chng.

Ging nhau

i nh

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: hai hon v (H:CH3 v CH3:OH) do chng i nh.

Nguyn t carbon pha di: khng cn han vchng c sn tnh i nh.

Stereochemistry

Hy cho bit mi quan h lp th ca hai phn t di y?

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Ha Lp Th

Nguyn t carbon pha trn: hai hon v (H:CH3 v CH3:OH) do chng i nh.

Nguyn t carbon pha di: khng cn han vchng c sn tnh i nh.

Do hai phn t l enantiomers

Stereochemistry

7/28/2019 hoa hoc lap the

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Ha Lp Th

Hai ln hon v trn cu trc ca phn t bn phi r rng chuyn hai phn t sang dng vt nh v nh gngca nhau

Stereochemistry

Hp cht Meso

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Ha Lp Th

Hp cht Meso l nhng hp cht c cc cha trung tm bt i, nhng li ctnh i xng ni phn t. Nhng loi phn t ny u c mt phng ixng ni phn t.

Mt phng i xng

Stereochemistry

Xc nh cc trung tm bt i trong phn t di yC mt phng i xng ni phn t no khng?

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Ha Lp Th

Stereochemistry

Mt ln hon v cho ra mt phng i xng ni ca ca phn t, do phn t ban u khng phi l hp cht meso

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Ha Lp Th

StereochemistryXc nh cc trung tm bt i trong phn t di y

C mt phng i xng ni phn t no khng?

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Ha Lp Th

Stereochemistry

Xc nh cc trung tm bt i trong phn t di yC mt phng i xng ni phn t no khng?

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Ha Lp Th

C mt phng i xng ni phn t no khng?

Meso

Stereochemistry

Hy cho bit mi quan h lp th ca cc phn t di y?

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Ha Lp Th

v

v

Stereochemistry

Hy cho bit mi quan h lp th ca cc phn t di y?

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Ha Lp Th

ng phn

khng i nh

e

i

Stereochemistry

Hy cho bit mi quan h lp th ca cc phn t di y?

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Ha Lp Th

ng phn

khng i nh

e

i

Ging nhau

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Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

t i ?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nhiii. Nu phn t l mt hp cht meso, khng cn xc nh tm bt

i m hy xc nh meso

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

t i ?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

t i ?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

t i ?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Khng c tm i xnghay cn gi l achiral cngha l vt v nh gngc th chng kht ln nhau.

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

tm i ng?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Khng c tm i xnghay cn gi l achiral cngha l vt v nh gngc th chng kht ln nhau.

2

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

tm i xng?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

tm i xng?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Khng c tm i xnghay cn gi l achiral cngha l vt v nh gngc th chng kht ln nhau.

Stereochemistry

i vi mi phn t di y hy:i. Nu phn t l bt i xng hy xc nh xem c tt c bao nhiu

tm i xng?

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Ha Lp Th

tm i xng?ii. Nu phn t khng c tm bt i, xc nh tnh trng vt nh

iii. Nu phn t l mt hp cht meso, khng cn xc nh tm bti m hy xc nh meso

Khng c tm i xnghay cn gi l achiral cngha l vt v nh gngc th chng kht ln nhau.

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Stereochemistry

C bao nhiu tm bt i trong cc phn t di y?y c phi l nhng phn t bt i hay khng?

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