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4-4 تفاعلات الآرينات PowerPoint PPT Presentation


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4-4 تفاعلات الآرينات

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4 4

4-4

  • : . 5,6-- (B) . (A) (C) .


4 4

  • (A) (B) .(C)


4 4

  • (1) (Nitration)

  • (2) (Sulfonation)

  • (3) (Halogenation)

  • (4) (Alkylation)

  • (5) (Acylation)

  • (6) (Azo coupling)


4 4

(1) :

  • (-NO2) . (+NO2) :


4 4

(2) :

  • -SO3H) ) . (+SO3H) :


4 4

(3) :

  • -X) ) (X2) (FeX3) . (X+) (Cl+) (Br+) :


4 4

(4) :( (

  • (-R) : (R-X) (AlCl3) (R+) :


4 4

  • (ROH) . (R+) :


4 4

(5) : ( - (

  • (RCO-) (R-COCl) (AlCl3) (R+CO) :


Site selectivity

(Site Selectivity)

  • (A) (E+) 2 4 3 12 (B)- 14 (C) - 13 (D)- .


4 4

. :

  • )) 2 () 4( ) - ( 2 4 .(


4 4

  • )) 2 () 4( ) 3 () - .


4 4

  • )) - -

  • (A) - (B) .

  • (F,Cl, Br, I)


4 4

  • -NO2, -SO3H,

  • -COOH, -COOR,

  • -COR, -CHO,

  • -CONHR,

  • -CN

  • -

  • - CH3, -CH2CH3

  • -OH, -OCH3, - OR

  • -NHCOR

  • -NH2, -NHR, -NR2

  • -OCOR,


4 4

-


4 4


4 4

  • :

  • (1) ()

  • (2)

  • (3)

  • -t (4)


4 4

(1)


4 4

  • 2- (A) 4- (B) (B) (A) .


4 4

(2)

  • .


4 4

4-5

  • :


4 4

  • :

  • )) (Nucleophilic Substitutions)

  • R - X + Nu- R - Nu + X-

  • )) (Elimination Reactions)


4 4

H2O

CH3OH

NH3

RNH2

RSH

HO-

NC-

CH3O-

I-; Cl-; Br-

RS-


4 4

  • .

  • ( ) :

  • (1) (R-X) ( (

  • (2) ( (

  • (3) ( .(


4 4

(1) (SN1)

  • :

  • (C-X)

  • .

  • R - X R+ + X-

  • R+ + Nu- R - Nu

  • __________________________

  • R - X + Nu- R - Nu + X-


4 4

  • (SN1) .

  • (SN1) .

  • .

  • .


2 sn 2

(2) (SN2) :

  • (C-X) (C-Nu) .

  • Nu- + R - X [NuR.X]- Nu-R + X-


4 4

  • (SN2) ()

  • (SN2) .

  • .


4 4

  • (SN1) :


4 4

  • : 2- -1- (B) 1- -3- (C) 2- (A) .


4 4

(SN1)

  • (SN1) (sp2) :


4 4

  • (SN1) - 1,4- -1- 1,4- .


4 4

(SN2)

  • .

  • .


4 4

  • (SN2) Z- E- 4 - - E - 4- Z - 4- .


4 4

  • . :

  • :

  • R-X + KCN R- CN + KX

  • :

  • R - X + RCOOAg R-COOR + AgX

  • :

  • R - X + NaSH R - SH + NaX


4 4

  • :

  • R - X + NaOH R - OH + NaX

  • :

  • R - X + RONa R - O - R + NaX

  • :

  • R - X + RSNa R - S - R + NaX

  • :

  • R - X + NH3 R- NH2 + HX

  • :


4 4

: -

  • . -


4 4

-

  • :

  • (1) (E1) (C-X) .


4 4

  • (SN1) (E1) (SN1) .


4 4

  • :

  • (1)

  • (2)

  • (3) .


4 4

  • (2) (E2) :

  • (C-X) (C-H) .


4 4

(E2)

  • (E2) .


4 4

  • (Saytzef).

  • ( ) .


4 4


4 4

  • :

  • (1) .

  • (2) .

  • (Hoffmann) :


Hoffmann

(Hoffmann) :

  • .

  • . - .


4 4

  • (1) :


4 4

  • (2)


4 4

: -

  • . .

  • R-X + Mg R-Mg-X

  • .

  • R-Mg-X + HOH R-H + HOMgX

  • .


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