HOA HOC HU C

Organic Chemistry
CHNG 4 HIEU NG TRONG HOA HU C

GII THIEU CHNG

GII THIEU PHAN LOAI HIEU NG HIEU NG CAM NG HIEU NG LIEN HP HIEU NG SIEU LIEN HP HIEU NG KHONG GIAN ANH HNG CUA CAC HIEU NG

HIEU NG CAM NG (INDUCTION) Hieu ng cam ng la s tac dung tng ho cua cac nguyen t, nhom nguyen t trong hp chat hydrocarbon no hoac khong no, khong lien hp gay ra.

HIEU NG CAM NG (INDUCTION)

ac iem cua hieu ng cam ng: -Do s chenh lech o am ien cua cac nguyen t, nhom nguyen t lam chuyen dch cac ien t lien ket xchma. -Hieu ng tat dan theo mach lien ket xchma ( qua 4-5 lien ket xchma). -Hieu ng cam ng dng ( + I) la hieu ng cho ien t va hieu ng cam ng am (-I) la hieu ng hut ien t. -Hieu ng cam ng tnh c hnh thanh do s chuyen dch ien t trong mach phan t trang thai tnh, co lap. Hieu ng cam ng ong xuat hien khi phan t trang thai chu tac ong ben ngoai (ang tham gia phan ng, dung moi, tac chat)

HIEU NG CAM NG (INDUCTION)

e xac nh tr so va dau cua hieu ng cam ng tnh dung hai phng phap: -So sanh hang so phan ly cua acid

-So sanh gia tr moment lng cc

HIEU NG CAM NG (INDUCTION)

So sanh hang so phan ly cua acid

HIEU NG CAM NG (INDUCTION)

So sanh moment lng cc

HIEU NG CAM NG (INDUCTION)

Mot so lu y:

-Yeu to khong gian t anh hng en hieu ng cam ng - Hieu ng I cua Csp > Csp2> Csp3

HIEU NG CAM NG (INDUCTION)

V du hieu ng tat dan theo mach

HIEU NG LIEN HP (CONJUGATION)

Hieu ng lien hp hay cong hng ch the hien nhng phan t co he thong lien ket pi va xch ma lien hp.

He lien hp pi-pi va n-pi ( he lien hp m rong)

HIEU NG LIEN HP (CONJUGATION)

Hieu ng lien hp hay cong hng ch the hien nhng phan t co he thong lien ket pi va xch ma lien hp.

He lien hp pi-pi va n-pi ( he lien hp m rong)

HIEU NG LIEN HP (CONJUGATION)

HIEU NG LIEN HP (CONJUGATION)

Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond

The p orbital can come from another double or triple bond The p orbital may be the empty p orbital of a carbocation or a p orbital with a single electron in it (a radical) Conjugation affords special stability to the molecule

1,3-Butadiene

Electron Delocalization Bond Lengths C-C : 1.54 C=C : 1.34

s bond between C2 and C3 made from sp2-sp2 overlap Overlap between the C2-C3 p orbitals

Allyl Cation

The energy of the allyl cation actual lower than the energy calculated for any the contributing resonance structures

Allyl cation stabilized by resonance effects

Allyl Radical

The Stability of the Allyl Radical Both molecular orbital theory and resonance theory can explain the stability of allyl radicals Molecular Orbital Description of the Allyl Radical the p orbital on the sp2 carbon overlaps with the p orbitals of the alkene The new p orbital is conjugated with the double bond p orbitals Delocalization of charge and electron density leads to increased stability

Allyl Radical

Resonance Description of the Allyl Radical

The

true structure of the allyl radical as suggested by resonance theory is as follows

Resonance
Benzene
H H C C H C H C C C H H

Writing Resonance Structures

When writing resonance structures the connectivity cannot be altered (only lone pair electrons and electrons in double and triple multiple bond can be moved).

A structure with the lowest magnitudes of formal charges is preferred (greater contribution to the hybrid).
A structure with a negative charge on the most electronegative atom is preferred.

Writing Resonance Structures

Resonance Structures
CH3NCO
H H H
+1 N 0 -1

. .

.. ..

0 C

0 C

H
-1 O

. . . .

H H

.. ..

..

0 C

0 C

H
0 O

0 C

0 C

..

+1 O

HIEU NG LIEN HP (CONJUGATION)

Hieu ng lien hp hay cong hng la s tac dung tng ho gia cac nguyen t hay nhom nguyen t trong he lien hp lam chuyen dch cac ien t lien ket pi gay ra s phan cc phan t . ac iem cua hieu ng lien hp: + S dch chuyen ien t pi ( ky hieu la mui ten cong) + Lan truyen suot mach lien hp. + Hieu ng lien hp dng ( + C) cho ien t. Hieu ng lien hp am (-C) hut ien t. = Hieu ng lien hp phu thuoc vao yeu to lap the: he se giam tnh lien hp khi mat hay giam cau tao phang

HIEU NG LIEN HP (CONJUGATION)

e xac nh dau va o ln tng oi cua hieu ng lien hp cua nguyen t hay nhom nguyen t da vao moment lng cc cua day cac hp chat thang va thm co cha cung mot nguyen t hay nhom nguyen t

HIEU NG LIEN HP (CONJUGATION)

Trong chu ky va phan nhom chnh theo chieu tang cua ien tch hat nhan, hieu ng lien hp dng (+C) giam. Cac nhom nguyen t co cap ien t khong lien ket se gay hieu ng lien hp dng.

HIEU NG LIEN HP (CONJUGATION)

HIEU NG LIEN HP (CONJUGATION)

HIEU NG SIEU LIEN HP (HYPERCONJUGATION)

HIEU NG SIEU LIEN HP (HYPERCONJUGATION)

HIEU NG SIEU LIEN HP (HYPERCONJUGATION)

HIEU NG KHONG GIAN

HIEU NG KHONG GIAN

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