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Bi tp tun 4

[1] Phn loi p ha hu c da vo kt qu ca p: p cng (addition reaction), p kh/tch loi

(elimination reaction), p th (substitution reaction), p chuyn v (rearrangement reaction).

[2] Phn loi p ha hu c da vo c ch p: p gc t do (radical reaction), p phn cc (polar

reaction), p xy ra thng qua mt trng thi chuyn tip vng duy nht (pericyclic reaction).

[3] i vi loi p phn cc: phn bit cht thn hch (nucleophile hay nucleus-loving), cht thn in
t (electrophile hay electron-loving).

[4] So snh bn tng i: carbocation, carbanion, gc t do.

[5] Danh php alken, so snh bn ca alken, tnh bt bo ha (degree of unsaturation).

[6] Cc p ha hc ca alken v c ch p. Lu s chuyn v carbocation (nu c) i vi nhng p

xy ra theo c ch qua trung gian carbocation. Ch ha lp th ca sn phm trong nhng p c
hc c ch.

1. Phn ng phn cc

Hu ht cc p hu c xy ra theo c ch phn cc (polar mechanism), trong tc cht thn hch

(nucleophile) cho i in t vo tc cht thn in t (electrophile) to thnh lin kt mi.

Tc cht nucleophile (thch in dng): c th trung tnh hoc mang in tch m; c th nh cc

carbanion, cc d nguyn t mang i in t t do, cc in t pi

Tc cht electrophile (thch in m): c th trung tnh hoc mang in tch dng; c th nh cc
cation (cha orbital trng), cc tm phn cc mang mt phn in tch dng (+)

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Mt s v d v p phn cc:

2. So snh bn tng i

Gc t do:

Carbocation

John E. McMurry (2015), Organic chemistry, 9th edition, chapter 11, Brooks Cole.

T.W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder (2013), Organic chemistry, 11th edition,
chapter 13, Wiley.

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Carbanion

Alken

n gin ha trong vic so snh bn tng i ca cc carbocation, carbanion v gc t do

ta c bng tm tt sau:

3. Mt s p iu ch alken

Dehydrohalogenation of alkyl halides Dehydration of alcohols

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4. Mt s phn ng ha hc ca alken

4.1. Cng hydrogen (H2) xc tc kim loi (Ni, Pt hoc Pd): cho sn phm cng kiu syn.

4.2. Cng halogen (X2): cho sn phm cng kiu anti qua trung gian ion halonium (bromonium,
cloronium) vng.

4.3. Cng HO-X (X2, H2O): cho sn phm halohydrin, c ch tng t p cng halogen.

4.4. Cng HX: qua trung gian carbocation (ch s chuyn v hydride hoc chuyn v metyl to
carbocation mi bn hn nu c).

4.5. Cng nc: c 3 loi p cng nc vo ni i C=C

Cng nc xc tc H+: qua trung gian carbocation (ch s chuyn v hydride hoc chuyn v metyl to
carbocation mi bn hn nu c).

Cng nc c mt mui thy ngn (II) acetate Hg(OAc)2 (OxymercurationDemercuration method): cho
sn phm cng kiu anti qua trung gian ion mecurinium vng.

S dng borane BH3 (Hydroboration-Oxidation method): cho sn phm cng kiu syn qua trung gian
trialkylborane (R3B).

4.6. Phn ng to epoxide: dng tc cht peroxyacid (RCO3H) cho sn phm cng kiu syn.

4.7. Phn ng tng hp 1,2-diol (2 nhm OH gn trn 2 carbon k cn nhau): c 3 phng php

S dng OsO4: to cis-1,2-diol

S dng KMnO4 long, lnh: to cis-1,2-diol

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Thy gii epoxide xc tc H+: to trans-1,2-diol

4.8. Phn ng ozon phn: nu carbon ni i khng cn hydrogen => ketone, cn hydrogen => aldehyde.

4.9. Phn ng vi KMnO4 trong mi trng acid: nu carbon ni i khng cn hydrogen => ketone,
cn mt hydrogen => aldehyde, cn hai hydrogen => CO2.

4.10. Phn ng tng hp cyclopropan: c 2 phng php

BI TP

Cu 1: Cho bit sn phm chnh ca cc phn ng sau:

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Cu 2: Gii thch s to thnh sn phm sau bng c ch phn ng:

H2SO4
+ CH3OH O

Cu 3*: Gii thch s to thnh cc sn phm sau bng c ch phn ng:

Bi tp Ha hu c 1 (c bn) 6