BAI 51 :

DAN XUAT HALOGEN CUA HIROCACBON

MUC TIEU CUA BAI HOC

1. Kien thc: Biet c: Khai niem, phan loai dan xuat halogen cua hirocacbon, tnh chat hoa hoc ac trng va ng dung cua mot so dan xuat halogen. 2. K nang - Viet CTCT cac ong phan cua dan xuat halogen cu the - Viet PTHH: Phan ng thuy phan( phan ng the) va phan ng tach cua dan xuat halogen, goi ten mot so dan xuat halogen.

I. KHAI NIEM, PHAN LOAI, ONG PHAN & DANH PHAP

1.Khai niem. Khi thay the nguyen t hiro cua phan t hirocacbon bang nguyen t halogen ta c dan xuat halogen cua hirocacbon VD H-C CH4 CH2=CH2 C6H6 DX halogen CH3Cl CH2=CH-Cl C6H5Br CH2Cl2 CH3Br

2. Phan loai: - Ban chat cua halogen - So lng nguyen t halogen - ac iem cau tao cua goc hirocacbon - Dan xuat halogen no (ankyl halogenua) VD: C2H5Cl : etyl clorua CHCl3 : Clorofom (triclometan) - Dan xuat halogen khng no ( anlyl halogenua) VD: CH2=CH-CH2Cl anlyl clorua - Dan xuat halogen thm(phenyl halogen) VD: C6H5Br : phenyl bromua hay brom benzen

*Da vao

* Cac loai dan xuat halogen

* Bac cua dan xuat halogen la bac cua nguyen t cacbon lien ket vi nguyen t halogen

VD - Bac I : CH3 CH2 Cl - Bac II: CH3 CH CH3 Cl - Bac III: CH3 CH3 C Br CH3

3. ong phan: Dan xuat Halogen co ong phan mach cacbon nh hirocacbon, ong thi co ong phan v tr nhom chc. VD: C4H9F 1) F CH2 CH2 CH2 CH3 1-flobutan 2) CH3 CH CH2 CH3
3) F CH2 CH CH3 F CH3 4) CH3 C CH3 CH3
F

2-flobutan

1-flometylpropan 2-flo-2- metylpropan

4. Danh phap: Ten thong thng VD: CHCl3 (clorofom) CHBr3 (bromofom) CHI3 (ioofom) Ten goc-chc Ten goc hirocacbon + halogenua VD: CH2Cl2 (metylen clorua) CH2=CH-F (vinyl florua) CH2=CH-CH2-Cl (anlyl clorua) C6H5-CH2-Br (benzyl bromua) Ten thay the Nguyen t halogen c coi la nhng nhom the VD: Cl2CHCH3 (1,1-icloetan) ClCH2CH2Cl (1,2-icloetan)

II. TNH CHAT VAT LY

ieu kien thng, cac dan xuat monohalogen co phan t khoi nho (CH3F, CH3Cl, CH3Br) la nhng chat kh. Cac dan xuat halogen co phan t khoi ln hn (CH3I, CH2Cl2, CHCl3, CCl4, C2H4Cl2, C6H5Br) thng the long, nang hn nc. Nhng dan xuat polihalogen co phan t khoi ln hn na (CHI3, C6H6Cl6) the ran. Cac dan xuat halogen hau nh khong tan trong nc, tan tot trong dung moi khong phan cc nh hirocacbon, ete Nhieu dan xuat halogen co hoat tnh sinh hoc cao (CHCl3 co tac dung gay me, C6H6Cl6 co tac dung diet sau bo)

III. TNH CHAT HOA HOC

1. Phan ng the nguyen t halogen bang nhom OH Ankyl halogenua khong phan ng vi H2O nhiet o thng

R-X +

Anlyl halogenua b thuy phan ngay khi ung soi vi nc RCH=CHCH2-X + H2O RCH=CHCH2-OH + HX
to

R-X + NaOH R-OH + NaX

to

OH-

R-OH + Xto

 Dan xuat phenil halogen (nhom X nh trc tiep vao vong benzen) khong

phan ng vi dd kiem nhiet o thng cung nh nhiet o cao, chung ch phan ng vi kiem ac nhiet o cao, ap suat cao.

C6H5Cl + 2NaOH

300oC,200atm

C6H5-ONa + NaCl +H2O

2. Phan ng tach hiro halogen

o

VD C2H5OH, t CH3 CH2Br + KOH ------- CH2=CH + KBr + H2O

Quy tac Zai-xep: khi tach HX khoi dan xuat halogen, nguyen t halogen (X) u tien tach ra cung vi H nguyen t C bac cao hn ben canh.
VD CH2 CH CH CH3 H Br H KOH, ancol, t0 HBr

CH3 CH = CH CH3 (sn phm chnh) CH2 = CH CH2 CH3 (sn phm ph)

3. Phn ng vi magie R X + Mg
ete khan

R Mg X (ankil magie halogenua)

VD: CH3CH2 Br + Mg CH3CH2 Mg Br

(Etyl magie bromua tan tt trong ete)

Hp chat c magie tac dung nhanh vi nhng hp chat co H linh ong nh (nc, ancol) va tac dung vi kh cacbonic

2CH3-CH2-MgBr + 2H2O
CH3-CH2-MgBr + R-OH C6H5-MgBr + CO2

2C2H6 + MgBr2 Mg(OH)2

C2H6 + R-O-MgBr C6H5-COOMgBr

4.Phn ng tng hp Wurtz

2R-X + 2Na R-R + 2NaX R-X + R-X + 2Na R-R + 2NaX Vd
2CH3Cl + 2Na C2H6 + 2NaCl CH3Cl + C2H5Cl + 2Na C3H8 + 2NaCl

ieu che: Co nhieu cach thu c dan xuat halogen theo nhieu cach khac nhau - Thay the nhom OH trong phan t ancol bang nguyen t halogen C2H5OH + HBr C2H5Br + H2O - Phn ng cng ca anken va halogen CH2=CH2 + HBr CH3-CH2-Br - The H cua hirocacbon bang nguyen t halogen as CH4 + Cl2 CH3Cl + HCl - T ankin CH CH + Br2 CH CH Br Br

VI. NG DUNG
1. Lam dung moi: metylen, clorofom, cacbon tetraclorua la nhng chat long hoa tan c nhieu chat hu c ong thi con de bay hi, de giai phong khoi hon hp. Lam nguyen lieu cho tong hp hu c: Cac dan xuat halogen cua etilen, butilen c dung lam monome tong hp polime quan trong. Cac ng dung khac: lam chat gay me trong phau thuat, diet sau bo, phong tr dch hai, diet co, kch thch sinh trng thc vat

2.

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