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I.

()
:

( );
( );
C

O
C
OH
O

-.

C
O

II.

:
NH2

;
;

NH

( );

O
Ar N

NH

O
C

NH

O
S
O

NH
O

CH N

NH

NH

NH

O
C

CH

III.

() ;

N

Hal

(Cl, Br, I, F).

1. , Alk-OH

:
(
);
, ;
(II) .
: , ,
.


, :
O

CH2OH
CHOH

+ 3

CH3

O
CH3

CH2OH

C
O

O
CH2O CH3
O
CHO CH3 + 3 CH3COOH
O
CH2O CH3

CH3CH + NaOH CH3COONa + HOH

..
3

,
, ,
:
O

CH3

C
O

CH3

2CH3 C

+ HOH

C
O
O

CH3 C

OH
O

+ NaOH

CH3 C

OH

+ H2O
ONa

:
CH3
+
OH
CH3

CH CH3

CH3

CH3

O
OC

CH3

CH

CH3

OH

CH3 O

O
+ NaOH

OH

+ CH3 C

O
CH3 C

CH3

CH3 C

+ H2O
ONa

= ..

.
.
, .
,
, .. ,

, ,
:
3CH3CH2OH+2K2Cr2O7+16HNO33CH3COOH+4Cr(NO2)2+4KNO3+11H2O
K2Cr2O7 + 6KI + 14HNO3 3I2 + 8KNO3 + 2Cr(NO3)3 + 7H2O
I2 + 2Na2S2O3 2NaI + Na2S4O6

..
4


.
. ,
,
. ;
(11) , ;
.
ONa

ONa
N
2 O2N

CH

OH

CH

CHCl2

CH2

N
+ CuSO4 + 2NaOH

O2N

CH

CH

OH

CHCl2

CH2
OH

Cu

+ NaSO4 + 2H2O

O
O2N

CH

OH
CH
N

CH2
C
ONa

, .

CHCl2

= 2 ..

2. ,

,
:
c (111);
(, );
;
;
;
.
.
,
.
KBrO3 + 5KBr + 6HCl 3Br2 + 6 KCl + 3H2O
OH

OH
Br

Br
+ 3HBr

+ 3Br2
OH

OH
Br

.


.
, .
,
, ,
, :
Br2 + 2KI I2 + 2KBr
I2 + 2Na2S2O3 Na2S4O6 + 2NaI

, :
, , , .

..
6


..
6

..
6

..
4

..
8

.
:
OH

OH
I

I
+ 3HCl

+ 3ICl

,
, :
HI + NaHCO3 NaI + H2O + CO2
HI + CH3COONa NaI + CH3COOH

.
.
I2 + 2Na2S2O3 2NaI + Na2S4O6
..

6

.
,
(I+Cl).
:
OH

OH
J

J
+ 3HCl

+ 3JCl

ICl + KI I2 + KCl
I2 + 2Na2S2O6 2NaI + Na2S4O6

..
6

( - 1, . 7).
.
O

C2H5
HO

CH

CH

OH + 2

C2H5

CH3

, >t 0

CH3C

CH3

C2H5
CH

CH

C2H5

CCH3

+ 2 CH3COOH

CH3COOH + NaOH CH3COONa + H2O

..
2


().
,

,
() , , .
()

(
)

, .
,
,
()
.
:
1.
2.
.
3. .
--

OH

H
+

C
O

O --

H
+
O

+ CH 3O-Na +

H
C
O

CH3

CH3

ONa

.. CH3
N
CH3

CH3

CH3

+ CH 3O-

+ CH 3OH
C
O

CH3

+ CH 3OH

CH3

:
ONa

OH
+ CH 3ONa

+ CH 3OH

= ..

3. ,
(, )
, (> =)
(
O

C
H

,
( )
C

, , C C CH2OH
O

.
, , ,
.
(, , ).

(
,

,
,
, ), (, );
( , ,
); (, ,
, ).
-
.
, (,
).
. .

, :
I2 + 2NaOH NaIO + NaI + H2O

:
O
+ NaJO

HC
H

+ NaOH

O
H

C
ONa

+ NaJ + H2O


,
:

NaIO + NaI + H2SO4 I2 + Na2SO4 + H2O


I2 + 2Na2S2O3 2NaI + Na2S4O6

HCOH + I2 + 3NaOH HCOONa + 2NaI + 2H2O


I2 + 2Na2S2O3 2NaI + Na2S4O6

..
2

, .

.
,
, ,
CH3
CH3
().
O

+ NH2OH . HCl

NOH
- H2O

+ HCl

HCl + NaOH NaCl + H2O

= ..

4. ,

OH

C
ONa

,
.
(
).
, . .
COOH

COONa
+ H2O

+ NaOH

= ..

, ,
( ).
.
(),
, ..

, .
COONa

COOH

+ HCl

+ NaCl
OH

OH

= ..

( ) .
,
H3N+CH2COO
. ,
, .
,
.
O
H2N

CH2 (CH2)2 COOH + H

CH2 (CH2)2 COOH


N

CH2

+ NaOH

C
H

- H2O

- H2O

CH2 (CH2)2 COOH


N CH2

()

CH2 (CH2)2 COONa


N

CH2

5. ,
,
.

( [] ).
, .
NH3 ;
NH2Alk ;
NH2Ar ;
HN< ;
N< .
, ,

.
5.1. ,


:
: (H2)6N4 + HCl (CH2)6N4 HCl

= ..

(-):
H3C

H3C

+ HCl

N . HCl

N
HO

=..

HO


.
( ):
O
H3C
O

N
N
CH3

CH3

+ HClO4

CH3COOH

H3C
O

N
+

CH3

CH3

ClO4

=..

, ,
,
.


-
() ,
, ..
.
.

NH
N

. HCl

CH2

NH

+ NaOH

. HCl
O

CH2 CH2 N

CH3

+ NaOH

+ NaCl + H2O
C2H5

C2H5

C2H5

CH2 CH2 N
C2H5

CH2OH

CH

+ NaCl + H2O

NH2

NH2

CH2

C6H5

H2SO4 + 2NaOH

CH3

CH2OH

CH

CH3 + Na2HPO4 + 2H2O

C6H5 + Na2SO4 + 2H2O

CH3O

CH3O

O
N

CH3 . H3PO4 + 2NaOH

OH

= ..
,

OH

..
2

( ).

- .
, ,

, .. (
).

+
R3N HCl R3N + Cl
H


:
O
CH3 C
CH3

O + Cl

O
CH3 C

+ CH3COO
Cl


:
HClO4 + CH3COOH ClO4 + CH3COOH2+

:
+
+
R3N + ClO4 [R3N] ClO4
H
H

:
CH3COO + CH3COOH2+ 2CH3COOH

( ), (
)
.

,
.
CH3COOH +
+
[R2N CH3]2 H2SO4 + HClO4 [R2N CH3] ClO4 + [R2N CH3] HSO4
H
H


.

, .

. :
R3N + nI2 + KI + HCl R3N nI2 HI + KCl

R3N HX + nI2 + KI R3N nI2 HI + KX

I2 + 2Na2S2O3 2NaI + Na2S4O6

. .
2n

, n ,

.

- .

.
.

:
NH

NO

C4H9

C4H9

+ NaNO2 + HCl
C

CH2 CH2 N

+ NaCl + H2O

CH3
C

CH3

CH2 CH2 N

CH3
CH3

= ..

,
.


.
. (,
)
, :
O
H3C
O

NH
N

H3C
+ AgNO3

N
N

Ag

+ HNO3

HNO3 + NaOH NaNO3 + H2O

= ..

5.2. ,



:
- ;
- ;
- ;
- .
,
,
.
()
.
+

NH2

N
+

CO
O

NaNO2 +

CH3

N
-

2HCl

Cl +
CO

NaCl +

2H2O

CH3

= ..


:
;
, , 00
, .
;

(
), ,
,
.

.
2 NaNO2 + 2KI + 4KCl I2 + 2NO + 2HCl + 2NaCl + 2H2O
I2 + KI +

(, ,
)

, ,
.
,
.
KBrO3 + 5KBr + 3H2SO4 3Br2 + 3K2SO4 + 3H2O
NH2

NH2
Br

Br
+ 2 HBr

+ 2 Br2
COC2H5

COC2H5

..
4

, ,
,

.
,
.
, .
.
I

COOH

COOH

+ 2ICl
H2N

OH

+ 2HCl
H2N

OH
I

ICl + KI I2 + KCl
I2 + 2Na2S2O3 2NaI + Na2S4O6

..
4


, -,
(, , .).
, .

6. ,

O
N


,
: Zn + 2HCl 2H + ZnCl2
.
7. , -
-
:
R

R1

O
OH

+ HO

O
--

+ H2O

, -
: ()
( ).
, ,
, .. .

, .
.
.
OH

C
O
OH

O
+ NaOH

>t

COONa

+
OH

NaOH + HCl NaCl + HOH

= ..

() ()
.

8. ,

, .
R

NH

R1

(
).
(,
), - (),
(, ),
(, ), , ,
, , .
, ,
: ()
( ).

,
(III) (II).
NH

NH2

CH3

O
+ CH3 C

+ NH2OH

NHOH

R
OH

OH

O
C

NH2

+ NH2OH

NH3

NHOH

+
N

R
3R

NH

OH

+ Fe

3+

C
O

NH

Fe + 3H
3

(I).
(II),
(III).
(IV).
:
C
O
OH

NH

>t k. H2SO4
- n CO
- n H2O

(NH4)2SO4

(NH4)2SO4 + 2NaOH NH3 + Na2SO4 + 2HOH (II)


NH3 + H3BO3 NH3 H3BO3

(III)

NH3 H3BO3 + HCl NH4Cl + H3BO3

(IV)

= ..

,
.

, ,
.
:
O
C

NH2

>t

+ NaOH

ONa

+ NH3

NH3 + H3BO3 NH3 H3BO3


NH3 H3BO3 + HCl NH4Cl + H3BO3

= ..

() ()
.

9. ,
.
()
R

CH
NH2

(CH2)n

O
OH

- HOH

CH

(CH2)n

NH

, :

-
(
,
,
, , ,
, , ).

. .
() ()
.

10-11. ,

H

10.

C
O

-2,4,6- (, , ,
, ); (); 5-
().
O

11.

: (, , ),
(, ), ().
, ,
, ..
,
.
, , .
H
N

R1

O
N
H

R2

OH

R1

HO

R2
O

, ,
,

.
.
NH2
NH2

S
O

..
N

OH

H
N

N
O

S
OH

N
N

OCH3

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

C2H5

+ NaOH
N

C2H5

C2H5

NaO

+ H2O

C2H5
O

= ..

,
( < 108),
().
(, , , ,
, ).
H

C2H5

O
N

C2H5

NaO
+ CH3ONa /

+ CH3OH
N

C2H5
O

H
O

C2H5

N
N
H

= ..

ONa
F

+ CH3ONa /
O

+ CH3OH
N
H

= ..

( ,
).
)
.

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

O
N

C2H5

NaO

+ HCl
N

+ NaCl
N

= ..

NH2

+ HCl
S

C2H5

NH2

C2H5

C2H5

ONa

/ + /

+ NaCl
O

CH3

NH

CH3

= ..

.
:
1. ,
.
.
,
.
H

C2H5

2O
N

N
+ Na2CO3

C6H5
O
O

H
N

+ AgNO3
N

C6H5

O
O
C2H5

NaO
N

+ H2O + CO2

C6H5

C2H5

NaO

C2H5

2 NaO

+ HNO3

C6H5
OAg


, (
):
O
O
N
NaO

C2H5
+ AgNO3

C6H5
OAg

AgO

C2H5
+ NaNO3

C6H5
OAg

= ..

2. .
( )
,
, - .
O

O
N

C2H5

NaO
N

C2H5

AgO

+ 2 AgNO3

+ 2 NaNO3
N

C6H5

C6H5
OAg

ONa

2AgNO3 + K2CrO4 Ag2CrO4 + 2KNO3

..
2

,
3
: ,
:
O
N

O
N

C2H5

NaO

+ AgNO3
N
O

C2H5

AgO

+ NaNO3

C6H5

C6H5
,
Na2CO3

C6H5
O

C
C6H5

2AgNO3 + K2CrO4 Ag2CrO4 + 2KNO3

= ..

( ,
). ,
,
,
, .
()
(, , ).

O
H
O

OAg

N
N
CH3

CH3

+ AgNO3

N
CH3

CH3

+ HNO3

HNO3 + NaOH NaNO3 + H2O

= ..

12. ,

,

. (, ,
, ), (, , ,
.), ()
(, , , ).

,
.
.

(
),
.
:
- : ()
() ;
-
(Zn + NaOH; Zn + CH3COOH) (
);
- (
);
- ( ,
);
- ;
-
( ;
).



-
.
.
, (), (, ) .
> t0
2Cu + Hal2 2CuCl

,
, ..
.


. .
(KNO3 + Na2CO3)
-:
-
()
O
H3CO

NH

(CH2)2

Cl

SO2NH

>t , KNO3 + Na2CO3

NaCl

HNO3
NaCl + AgNO3 AgCl + NaNO3

AgCl + 2NH4OH [Ag(NH3)2]Cl + 2H2O

-
.
- ().
I
HO

I
O

CH2 CH

COOH

NH2

>t , KNO3 + Na2CO3

I
I
HO

I
O

CH2 CH
NH2

I
2NaI + Cl2

I
I2 + 2NaCl

COOH

7 NaI

,
( ):
(
) ,
,
;
O2N

CH

NH

COCHCl2

CH

CH2OH

NaOH, >t

2 NaCl

OH

HNO3
NaCl + AgNO3 AgCl + NaNO3

(
):
> t0
C2H5Cl + NaOH C2H5OH + NaCl
HNO3
NaCl + AgNO3 AgCl + NaNO3

:
( , ,
,
, ). -
.
.
Zn + 2NaOH Na2ZnO2 + 2H
CH3
O

[H]

NaBr

Br


.
-

.

Zr4+
.
- .
, , , :
> t0 Na
R F NaF
Zr(Aliz)4 + 6NaF Na2[ZrF6] + 4AlizNa
-


, ,

( )
. Cl .
OH
Cl

>t ,O2

HCl

NH
SO2NH2
O


,
,

.

-.

-
:
O2N

CH

NH

COCHCl2

CH

CH2OH

NaOH, >t

2 NaCl

OH

HNO3
NaCl + AgNO3 AgCl + NaNO2

AgNO3 + NH4SCN AgSCN + NH4NO3

NH4SCN + Fe3+ Fe(SCN)3 + NH4 +

..
2



.

,
.
, .


.
CH3
O

NaOH + Zn

NaBr

Br

3SCN + Fe III Fe(SCN)3



NaBr + AgNO3 AgBr + NaNO3
Fe(SCN)3 + 3AgNO3 3AgSCN + Fe(NO3)3

= ..



- , ..
( ).
O
CH3

I
NH

O
NH

CH3

(NaOH + Zn)

3 NaI

I
CH2 CH

COOH

C2H5

NaI + AgNO3 3AgI + NaNO3

..
3


(, ).


(I), (IV, V).
(II),
(III), ..

(I):
KMnO4+H2SO4
RI KIO3

(I)

2KMnO4+5NaNO2+3H2SO4 2MnSO4+5NaNO3+K2SO4+3H2O
2 NaNO2 + H2N

C
O

NH2 + H2SO4

2N2 + CO2

(II)

+ Na2SO4 + 3H2O

(III)

KIO3 + 5KI + 3H2SO4 3I2 + K2SO4+3H2O

(IV)

I2 + 2Na2S2O3 2NaI + Na2S4O6


. .

,
6n

(V)

n
( )

. .
,
6

( 1, .1, .181).

, ,
,
.
-
,
,
-

( ).
2Cl + Hg(NO3)2 HgCl2 + 2NO3

.
.

, .
,
( ).
[O]
[O]
RI I2 IO3
IO3 + 5I + 6H+ 3I2 + 3H2O
I2 + 2Na2S2O3 2NaI + Na2S4O6

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