1.

() e
1.1

H2C-CH- CH

CH2 CH3

CH3

??

2
1

3-

2
3

7
4

1.2.

2

CH2 CH CH2 CH3

CH2 CH CH CH3

( )

( a)

1-

2-

Ko

2
3

Cl

6--4,5--2-e

1.3.

1

CH2 CH

CH

CH2CH3

CH3
3--1-

H3C

2
3
4

H3C

1
6

3-

6-

1.4.

H3C
H

H3C

CH3

-2-

H
CH3

-2-

H
1

-4--2-en

1.4. a) - ()

H
H
( )

H 3C

CH2CH3

-
-e

1.5. (
)
E,Z-
a) E
()
b) :
=
-

C(3)
C > H

H3C
H

CH2Cl
Br

(E) -2--1--2-

C(2)
Br > C

c) =

C(3)

C(2)
H3C H H H
H3C C 3 2 C CH3
C C
HHO > HHC
H3C
C OH
H
H

CCH > HHH

5

4
3

2
1

OH

(E)-2--3,4--2--1-

d) Z (zusammen)
()

C(3)

F> C(H3)

2
3

O
1

CH3
OH

C(2)
O(CH3) > C(OH)

(Z)-3--2--2--1-

1.6. = .
a) (a .) =

1
2 OH
3

CH2 CHCH2OH

Cl 5 4

2--1-o

(Z)-3--5--4--2-o
NH2
1

5
6

4
5

3--2-a

3
4

4--2-o

Ko e je o

CH2 CH2OCH3

7. a

H 2C

H2C

CH

E ()

H
H 3C

C C

-1-

CH CH2

2- ()

H2C

H3CHC

CH

1-

CH2

CH3CH

()

2. -
-

H
H

C
sp2-o

2p-o

H
120

H
H

H 121.7 H
116.5
C C
1.076 A
H
H
1.33 A

 - 108 Kcal/mol; - slabija 65

Kcal/mol
( );

A ,
( ); cis- trans-;
-
> 400C
( );
(, , .. )

2.1.
O
(
= )

CH3CH2

H
C C
H

H
CH3
C

CH3

H
C

C
CH3

CH3CH2CH2CH3 H = -30.3 Kcal/mol

H2/ Pt

CH3

H2/ Pt

H2/ Pt

CH3CH2CH2CH3

CH3CH2CH2CH3

H = -28.6 Kcal/mol

H = -27.6 Kcal/mol

2.2.Ma
H R
R
R
R2C=CR2> R2C=CHR > C=C > C=C > RCH=CH2> H2C=CH2
R H
H
H

1. ( - C-H
o)
R2C=CR2

R
C
H

C
R
trans

R
C
H

C
H

cis

cis-

3.
3.1.

H CH3
H3CC C CH3
H Br

- +

C2H5O- Na+

CH3

H3C

H3CCH C
C2H5OH, 70C
CH3

H3CCH2

Saytzev-

70 %

C CH2
30 %

E H

C2H5O

H
H C
H3C

CH3
CH3
Br

Na

-C2H5OH

+
-Na Br

H3C

CH3
CH3

2--2-

3.2.
( Saitzev )

80%

OH
H3CC
H

CH2CH3

H2SO4
100 C

H3CCH CHCH3

20%

H2C CHCH2CH3

HOH

4.0. -

H
H

-,
-

(Nu)
: a OH-, X-, RO- Lewis-

NH3, ROH...

()

E ( (H ,+ , R3C , +
, )
, Lewis-ove kiseline (BH3), karbeni ( CH2)

5.
5. 1. Re,
5. 2. e
5. 3. ok

5. 1. ,

CH3CH=CH2

H H

H2/PtO2
1 atm., 25oC
ili H2, Pd/C
ili H2/Raney Ni

CH3CH2CH3

C C

C C
H

e
- :
5.2.1. (X2)
+
5.2.2. (H +)
5.2.1.e =
()

C C

X X

X
C C
X

Br2/CCl4

Br

Br

Br

Br
C C

I :

Br

Br
C C
Br

Br
C

C
Br

II :
Br-,
(anti a)

A
trans- (anti-a)

Br
Br2/CCl4
Br
trans-1,2-

5.2.2. E (H+ )
a
(a HX, HOH/H+,H2SO4..)
O :

+ +
(H ) C

(H ) C
(Markovnikov )

CH3CH CH2
H

A

Cl
CH3CH CH3

Cl-

CH3CH CH2 H Cl
HCl

CH3CH CH2
H

CH3CH CH2
H

CH3CH CH2
H
2

E H =


+
+
+
+
R3C > R2CH > RCH2 > CH3
1
3
2
HX
(CH3)2C=CH2 > CH3CH=CHCH3 > CH3CH=CH2>
CH2=CH2 > ClCH=CHCl

CH3 + CH3
C
+I
+I
CH3
+I

+I e
e e-
( )

Ka ?

H
H
H

C
C
H

H
C

C
H

(CH3)3CCH CH2 HCl

3,3--1-

H3C

CH CH3
C
CH3
CH3

1,2- . 2
3

(CH3)3CCHCH3
Cl
2--3,3-

H3C
CH3

CH CH3

CH3

ClCH3

+ CH3 C

CH CH3

Cl CH3
2--2,3-

A :
() : i a H2SO4;
ii

CH3
CH3
CH3
i H OSO3H
ii H2O
H3C C CH3
H3C C CH3
H3C C CH2

OSO3H
OH
2-

2-

E :
A HOH
CH2

HOH, H

CH3

H2O

OH
CH3

1-

A HBr
( -
Markovnikov )

RO OR
RO

HBr

H3C CH CH2
Br
H3C CH CH2

2 RO
RO H

Br

Br (E)

H3C CH CH2 Br
2

HBr

H3C CH2 CH2Br

+ Br

.
,

CH3-CH(CH3)-CH=CH2

1. BH3, THF
2. H2O2, NaOH, H2O

CH3CH(CH3)-CH2-CH2-OH

CH3-CH(CH3)-CH=CH2

Br2, H2O

CH3-CH(CH3)-CH(OH)-CH2-Br

CH3-CH(CH3)-CH=CH2

Br2, CH3OH

CH3-CH(CH3)- CH(OCH3)-CH2-Br

 nO4 pH 7
(OH . -)

 (RCO3H)
()

CO3H
Cl

CH3CO3H ili H2O2/CH3CO2H

R
R

C CH2

O3

R
R
O

CH2
O

R
O

CH2

Zn/H2O

E O3

R
R

O CH2
,
C=C veze

R
R

C CH2

 C=C
(
)

KMnO4
(CH3)2C CHCH3
pH < 7
2--2-

H3C
H3C

CH3
OH

H2C CH CH3

C
H

Br2 /300oC

C CH3
H

NBS

H2C CH CH2
Br

C
H

C CH2
H
Br

O
H2C

N Br

H2C
O

Br
NBS

Br

(NBS)