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A лкени PowerPoint PPT Presentation


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се НЕЗАСИТЕНИ ЈАГЛЕВОДОРОДИ што во својот состав содржат НАЈМАЛКУ ЕДНА С=С ДВОЈНА ВРСКА. Општа формула C n H 2n. A лкени. A лкени C n H 2n “ незаситени ” јаглеводороди C 2 H 4 e тилен Функционална група = јаглерод-јаглерод двојна врска

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A

=

CnH2n

A


A

ACnH2n

C2H4 e

= -

sp2 => , 120o

& => H2C=CH2

!


A

p2


A

- -

C3H6 CH3CH=CH2

C4H8 CH3CH2CH=CH2

-

1-

CH3

CH3CH=CHCH3 CH3C=CH2

-

2-2-


A

2-:

cis-2-trans-2-

()


A

C=C

, (cis-trans) .

CH3CH=CHCH3 CH3CH2CH=CH2

CH3

(CH3)2C=CHCH3CH3CH=CCH2CH3


A

cis-trans-. IUPAC .

cis-

????????


A

  • E/Z IUPAC .

  • * .

  • 2. * * *

  • *

  • (Z)- zusammen (E)- entgegen

  • o


A

*

*

(Z)-

(E)-

*

*


A

  • , a:

  • = C=C.

  • a =>

  • - , .

  • .

  • , E/Z (cis/trans) .

  • ?

  • -- , , .


A

*

*

(Z)-3--2-

(3--cis-2-)

*

(E)-1--1-

*


A

(, ), .

, ,

-o e

CH2=CHCH2-OH2--1-o

CH3CHCH=CH23--2-o

OH


A

:

-

../.. ~ a

:


A

  • a:

  • 2.

  • 4. ()


A

  • R-X (X=Cl, F, Br)

  • | | | |

  • C C + KOH(a.) C = C + KX + H2O

  • | |

  • H X

  • RX: 3o > 2o > 1o

  • Saytzeff- o

  • = k [RX] [KOH]

  • = E2


A

= k [RX] [KOH] => RX & KOH RDS

R-I > R-Br > R-Cl e

=> CX RDS

R-H > R-D

=> CH RDS

: CX CH .


A

Me = e, E2

! .

(OH-)


A

CH3CHCH3 + KOH(alc) CH3CH=CH2

Br

-Br -

CH3CH2CH2CH2-Br + KOH(alc) CH3CH2CH=CH2

n- 1-

A ?

CH3CH2CHCH3 + KOH(alc) CH3CH2CH=CH2

Br 1-19%

sec-+

CH3CH=CHCH3

2-81%


A

8.6. ( ) a ?

CH3CH3

KOH(alc) + CH3CCH3 CH3CHCH2-X

X

1- KOH(alc) + CH3CH2CH2CH2CH2-X

: CH3CH2CH2CHCH3 !

X

2- KOH(alc) + CH3CH2CHCH2CH3

X

2--2- KOH(a) + !


A

!

2--2-


A

  • :

  • | |||

  • C C , C = C + H2O

  • | |

  • H OH

  • ROH: 3o > 2o > 1o

  • Saytzeff

  • E1

  • : #3 !


A


A

CH3CH2-OH + 95% H2SO4, 170oC CH2=CH2

CH3 CH3

CH3CCH3 + 20% H2SO4, 85-90oC CH3C=CH2

OH

CH3CH2CHCH3 + 60% H2SO4, 100oC CH3CH=CHCH3

OH

+ CH3CH2CH=CH2

CH3CH2CH2CH2-OH + H+, 140oC CH3CH2CH=CH2

! + CH3CH=CHCH3


A

1- 1-:

CH3CH2CH2CH2-OH + HBr CH3CH2CH2CH2-Br

SN2 E2 KOH(alc)

CH3CH2CH=CH2

!

, .


A

  • | | | |

  • C C + Zn C = C + ZnX2

  • ||

  • X X

  • .

  • CH3CH2CHCH2 + Zn CH3CH2CH=CH2 + ZnBr2

  • Br Br

  • . - .


A

  • , a:

  • E2

  • 2.

  • E1

  • 4. ()


A

R-OH

H+

R-X

KOH

A

(a.)

Zn


A

  • HX

( )


A

r.d.s.

Me:

II. - (M )


Ii me

H+, .

. X-

II. - (Me )

()

2nd ?


Ii me1

II. - (Me )

a

b


A

.

EA1 , .

EA2 , , .

II. - ( )

a,b (a )


Ii me2

(I)

(II)

II. - (Me )


Ii me3

e carbonium ion (II) .Carbonium ion (II) 2 a (.), carbonium carbonium ion (I) ( ). (r.d.s.) (II) .

II. - (Me )


A

(1ry carbonim ion)

+

(2ry carbonium ion)

C

H

C

H

C

H

3

3

+

C

H

C

H

C

H

3

2

2

II. - (M )

2ry carbonium

.


A

Markownikoff-

( ) H !!!., . , , carbonium .

carbonium :

3ry C+ > 2ry C+ > 1ry C+ > CH3+

II.


A

HBr -


A

+

-

H

O

2

C

C

+

H

.

H

S

O

C

C

C

C

4

b

o

i

l

H

O

S

O

H

H

O

H

3

  • (contd)

    conc.

II.

,

.


Ii conc

Markovnikoff?

/ ?

II. - conc.

, CH3CH2CH2OH, ?

, CH3CH(OH)CH3, ?

, (CH3)3COH, ?


A

+

-

  • (contd)

    HOX (Cl2 )

II.


A

A ()

II.


A

e , C=C . . .

carbonium.

+ve brominium. .

II.


A

  • A ( e)

    Hydrogenation

II.

  • a

  • o .

  • b. .


A

  • O ( )

II.


A

. R=H a , H2O2 . , . , .

. :

CH3CH2COCH3 and CH3CH2 CH2CHO

:

II.


A

+

[

O

]

C

C

+

H

O

C

C

2

O

H

O

H

-

-

f

Mn

O

/

O

H

4

  • O

    • () ()

II.


A

  • ( )

II.

MnO4- / H+

,

.


A

, CO2 , .

II.

MnO4- / H+


A

  • .

    :

    Ziegler-

II.


A

:

Propagation:

II.

:


A

n

n

n

m

n+m+2

Te:

II.


A

.

: 50000g

: 126oC 135oC ( )

:

, ( sigma ) ( H-), . - .

II.


A

:

II.


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