HIN TNG NG PHN

TS. BI TH BU HU KHOA KHOA HC T NHIN

NG PHN

NG PHN PHNG
ng phn khng i quang ng phn Cis-trans

NG PHN LP TH
ng phn i quang

ng phn Cu trng

NG PHN CU TRNG
S quay xung quanh mt lin kt s l c php

NG PHN CU TRNG
C th c nhiu cch sp xp trong khng gian khc nhau ca cc nguyn t trong phn t H2O2

Cu trng (Conformation): L bt k cch sp xp

trong khng gian 3 chiu ca cc nguyn t trong phn t c c do s quay xung quanh mt lin kt n

ALKANE

ALKANE

PHP CHIU NEWMAN

Cng thc phi cnh Cng thc phi cnh

Cng thc chiu Newman Cng thc chiu Newman

V cng thc phi cnh v cng thc chiu Newman ca 1,2-dichloroethane ?

H H Cl C C Cl

H H

1,2-dichloroethane
H Cl H H H Cl H H Cl H H H Cl Cl H H Cl Cl H H Cl H Cl H H H H H Cl Cl H H H H H Cl Cl H H H

HCl H

Cl H H Cl

Cu trc alkane ?

GC NH DIN (Dihedral angle, Torsion angle)

L gc to bi mt phng H-C-C v mt phng C-C-H D dng quan st t cng thc Newman

ETHANE
Tn ti v s cu trng khc nhau

Hai cu trng gii hn: Che khut v Lch

Cu trng lch

Bn nht

Cu trng che khut

Km bn nht

ETHANE

ETHANE

SC CNG NH DIN (Torsional strain) S khc nhau v nng lng gia cu trng lch v cu trng che khut: ~3 kcal/mol
Sc cng nh din: sc cng do s tin n gn nhau ca cc nguyn t hoc cc nhm nguyn t t cu trng lch n cu trng che khut.

BUTHANE
S quay xung quanh lin kt C1-C2

Cu trng lch

Cu trng che khut

BUTHANE: Cu trng do s quay chung quanh C2-C3

Cu trng bn lch, = 60 (gauche conformation)

BUTHANE: Cu trng do s quay chung quanh C2-C3

Cu trng lch hon ton, = 180 (anti conformation)

BUTHANE: Lin kt C2-C3

SC CNG GC (Angle strain)

Xut hin khi gc lin kt trong phn t tr nn nh hn hoc ln hn so vi bnh thng

Hoc xut hin khi mt lin kt tr nn ngn hn hay di hn so vi di bnh thng ca lin kt
Xut hin do tng tc gia cc lin kt

Tng tc lp th (Steric strain)

L nng lng thm vo phn t khi cc

nguyn t hoc cc nhm nguyn t qu gn nhau trong khng gian tng lc y Van der Waals gia cc m my in t

Xut hin do tng tc gia cc nhm

CU TRNG CA PENTANE Mch carbon thng: Cu trng bn nht tng ng vi tt c cc lin kt C-C u cu trng anti Khung carbon sp xp theo kiu zigzag

CU TRNG CA HEXANE

CYCLOALKANE: SC CNG VNG

Hp cht vng 5 hoc 6 carbon hin din rt nhiu trong t nhin trong khi hp cht vng 4 hoc 3 carbon rt t: Do sc cng vng ?

Cyclopentane phng Gc lin kt = 108

Cyclopropane phng Gc lin kt = 60

(Gc lin kt trong t din = 1095)

CYCLOPROPANE: SC CNG VNG

S xen ph hiu qu

S xen ph km hiu qu

Xen ph sp3-sp3 km hiu qu

CYCLOPROPANE: SC CNG NH DIN

Ngoi sc cng vng, cyclopropane

cn chu sc cng nh din (torsional

strain) do cc lin kt u b che

khut

CYCLOBUTANE

CYCLOHEXANE

CYCLOPENTANE

CYCLOHEXANE: CU TRNG GH

CYCLOHEXANE: CU TRNG THUYN

CYCLOHEXANE

CYCLOHEXANE

CYCLOHEXANE MANG MT NHM TH

Ti sao nhm methyl v tr xch o bn hn?

CYCLOHEXANE MANG MT NHM TH

S khc nhau v nng lng: 7 kJ/mol

CYCLOHEXANE
1. Methyl (hng xung) C-6: trc hay xch o? 2. Methyl (hng ln) C-1 bn hn hay km bn hn methyl (hng ln) C-4? 3. t methyl C-3 theo hng bn nht? (hng ln hay xung?)

1. Methyl (hng xung) C-6: trc hay xch o?

2. Methyl (hng ln) C-1 bn hn hay km bn hn methyl (hng ln) C-4?

3. t methyl C-3 theo hng bn nht? Hng ln hay xung?

Nhm alkyl bn nht khi v tr xch o

CYCLOHEXANE MANG MT NHM TH

CYCLOHEXANE MANG MT NHM TH

Cu trng bn nht ca 1-tert-butyl-1-methylcyclohexane ?

Nhm tert-butyl ln hn nhm methyl

CYCLOHEXANE 1,4-HAI LN TH

ng phn trans c nng lng thp hn (bn hn) ng phn cis 7 kJ/mol

1,4-DISUBSTITUTED CYCLOHEXANE

1,2-DISUBSTITUTED CYCLOHEXANE

Trans-1,2-Dimethylcyclohexane

1,2-DISUBSTITUTED CYCLOHEXANE

1,3-DISUBSTITUTED CYCLOHEXANE

Cu trc bn ?
1. trans-1-tert-Butyl-3-methylcyclohexane
2. cis-1-tert-Butyl-3-methylcyclohexane

3. trans-1-tert-Butyl-4-methylcyclohexane
4. cis-1-tert-Butyl-4-methylcyclohexane

trans-1-tert-butyl-3-methylcyclohexane
Nhm tert-butyl ln: v tr xch o
Thm nhm methyl: v tr trans i vi nhm tert-butyl

cis-1-tert-Butyl-3-methylcyclohexane

trans-1-tert-Butyl-4-methylcyclohexane

cis-1-tert-Butyl-4-methylcyclohexane