Органическая химия: Методические указания и лабораторные работы по специальности ''Биология

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  • 011600 ( . .04.3)

    2003

  • 2

    , 4 24 2003 .

    : ., . .. . .

    ., . .. . .

    ., . .. ..

    ., . .. . .

    ., . .. . .

    . . .

    .

    2 .

  • 3

    .*

    1. . 4 .

    2. . 4 .

    3-4. 8

    . . . . .

    -

    5. , .

    4 , .

    - ,

    6. --//-- 4 , . --//-- 7. --//-- 4 . --//-- 8. --//-- 4 . --//--

    9. . 4 , , , . -

    10. , .

    4 , , .

    - ,

    11. --//-- 4 , . --//--

    12. --//-- 4 . --//--

    13. . 4

    --//--

    14. , .

    4

    - ,

    15. --//-- 4 . --//-- 16. --//-- 4 -, -, . --//-- 17. --//-- 4 . --//--

    18. . 4 .

  • 4 * 1-2 .

    .

    1. , . 2. . . 3. . , . 4. . 5. , , . 6. : , . 7. ( ) , ( ) , . 8. ; , . 9. - . , . 10. , . , , , . 11. . , , . , . , . 12. ( ), . , .

  • 5 13. , , , . . ( ). 14. , , , . , . 15. 0,5%- , . 16. 10-15 . , 3%- (NaHCO3). , 2-3%- . 17. , 1%- . , 0,5%- ; . 18. (, ). 19. , 3%- . , , , .

    .

    . , . : , , , , , .

    , ,

  • 6 , . .

    1. .

    . , . , , , . , .

    ( ).

    :

    C + 2CuO 2Cu + CO2

    CO2 + Ca(OH)2 CaCO3 + H2O

    t

    2. , .

    . ( ), - . , (, !).

    , . , , . ; . .

    2. 1. .

    ) I , , . -

  • 7 , .

    Pb(NO3)2 + 4NaOH 2NaNO3 + Na2PbO2 + 2H2O Na2S + Na2PbO2 + H2O PbS + 4NaOH

    ) I 1-2

    . - - .

    Na2[ F e(CN)5NO ] + Na2S Na3[ Fe(CN)5ONSNa ]

    2. 2. .

    , 1-2 ., , 3-5 . . , . , .

    FeSO4 + 2NaCN Fe(CN)2 + Na2SO4

    3Na4[ Fe(CN)6 ] + 2FeSO4 Fe4[ Fe(CN)6 ]3 + 6Na2SO4

    Fe(CN)2 + 4NaCN Na4[ Fe(CN)6 ]

    2. 3. . )

    ( !) , . .

    .

    NaHal + AgNO3 AgHal + NaNO3

    ) :

    . , . .

    .

  • 8 , (

    , ), , , - , . .

    .

    I. ( ). .

    . , , , . , , , . . .

    ( NaOH Ca(OH)2) :

    II. ( ).

    . I , ,

    4 . , . . , .

    :

    CH3CH2OH + HOSO2OH CH3CH2OSO2OH + H2O

    CH2 = CH2 + HOSO2OHCH3CH2OSO2OH . :

    CH2 = CH2 + Br2 BrCH2 - CH 2Br

    1,2- MnO4(-) - :

    CH3 - C CH4 + Na2CO3O

    + NaOHONa

  • 9

    OH

    3CH2 = CH2 + 2KMnO4 + 4H2O 3CH2 - CH2 + 2MnO2 + 2KOH

    OH

    III. ( ). .

    . , : 1) , 2) , 3) , 4) . . , .

    :

    + + Ca(OH)2

    HOHCa

    C

    C HOH CH

    CH

    : 1)

    1,2-

    CH CH + Br2 BrCH = CHBr Br2CH - CHBr2+Br2 1,1,2,2-

    2) MnO4(-) KMnO4CH HCOOH + CO2CH p - p

    3) g ( Cu) + 2[ Ag(NH3)2 ]OH AgC CAg + 4NH3 + 2H2OCH CH

    IV. ( ). .

    1) : 2 4 . . , , .

    COONa

    + NaOH + Na2CO3

  • 10

    2) : 2 2,5 . 1 . ( 15 ) , . - - . .

    CH3 CH3 NO2

    +

    CH3

    NO2 - n -

    HNO3

    -H2O; H2SO4

    3) : 4

    , 4 , 1 CCl4. , . . ( ) HBr ( ) , . , .

    CH3

    CH3Br

    CH3

    Br

    Br

    CH2Br

    - n -

    + Br2

    Fe + HBr

    +

    + 2Br2

    + 2HBr

    + 2HBr

    th

    2

    2

    Fe

    4) :

    1 1 , - .

  • 11 . , .

    COOHCH3

    H2SO4

    KMnO4

    KMnO4

    H2SO4

    V. , , .

    . . 1. .

    . . , , , . . 5 .

    2. .

    2.1. . 1 1

    . , , . , 5-10 , .

    2C2H5OH + 2Na 2C2H5ONa + H2

    H2O NaOHC2H5ONa + C2H5OH +

  • 12 C2H5OH + C2H5OSO2OH + H2OHOSO2OH

    H2SO4C2H5OC2H5 +C2H5OSO2OH + C2H5OHt

    2.2. . 2 , 2

    1 , . 2-3 , , .

    3. . 6 3

    - 0,5 . 0,5 . - ; - .

    H2SO4CH3CH - CH2 - CH2OH

    K2Cr2O7

    CH3

    O

    H

    CH3 - CH - CH2 - C

    CH3

    H2SO4

    K2Cr2O7 O

    H

    CH3 - CH - CH2 - C

    CH3

    4. . :

    3-4 2-3 .

    C

    O

    O

    CH3

    CH2 CH2

    CH3

    CH CH3

    + H2OH2SO4

    C

    O

    OH

    CH3 CH CH2

    CH3

    CH3 CH2OH+

    ( )

    CH3 CH2 OH + [O] CH3 CH

    O

    NaIO + CH3 CO

    I2 + 2 NaOH NaIO + NaI + H2O; NaIO NaI + [O]

    + H2O

    CHI3 + HCOONa + 2NaOH3

  • 13 60 , 0,5-1 , . .

    . . 1. .

    , . 3-5 : , . . .

    CH2OH + Cu(OH)2 +HO - CH2 CH2 - O Cu

    O - CH2 + H2OCH2OH HO - CH2 CH2 - O O - CH2

    H

    H

    2. .

    1 , . , .

    . .

    1. . 0,5 ( )

    . .

    CH2

    CH

    OH

    OH

    CH2 OH

    OH

    Cu

    OH

    CH2

    CH

    CH2OH

    OH

    OH

    + + CH2

    CH

    CH2OH

    O

    O

    CH2

    CH

    OH

    O

    CH2 OCu

    H

    H

    CH2

    OH

    CH

    OH

    CH2

    OHCH2 CH C

    H

    O

    + 2H2O

    OH ONa

    + NaOH + H2O

  • 14

    2. .

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

    + 3HCl

    H

    6C6H5OH + FeCl3

    H5C6O OC6H5

    C6H5

    O

    FeH5C6O OC6H5

    O

    C6H5

    H

    H

    3. . 2 2%-

    ( 5 ). 2,4,6- .

    OH

    + 3Br2

    Br+ 3HBr

    OH Br

    Br

    4. . 1

    3 2 . NH4OH, 3 . .

    OH NOH ONH4OH

    HBr

    + Na2SO4+ H2SO4

    ONaOH

    2 2

  • 15 .

    5. .

    0,5-1 . , - .

    VI. , .

    . .

    1. . ) : 3-4

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

    2Cu + O2 2CuO

    C2H5OH + CuO CH3CO

    H+ H2O + Cu

    , .

    K2Cr2O7H2SO4, t

    + H2OC2H5OH CH3CO

    H ) : 0,5

    , . 0,5 , .

    1 . .

    , .

    CH3 C

    O

    ONa NaO C

    O

    CH3 CH3 C

    O

    CH3 + Na2CO3+

  • 16

    2. . ) (

    ): 1 , 1 1 . , 50-60 .

    , .

    R = H, CH3 ) : 1

    ( ) 0,5 . , .

    R = H, CH3

    3. , .

    ) : 1 . .

    ) : 1-2 , 1-2 1%- (Na2NOFe(CN)5) 10%- . .

    4.

    . 1 5

    . 1

    C

    O

    H

    R + 2[Ag(NH3)2] OH+ -

    C

    O

    OH

    R + 4NH3 + H2O + 2Ag

    O

    H

    R

    O

    OH

    R+ Cu(OH)2 + H2O + Cu

    CuSO4 + NaOH Na2SO4 + Cu(OH)2

  • 17 , 1, - .

    .

    . .

    1. .

    1-2 2-3 . ( ) , .

    .

    2. - . 1-2

    5-6 , . .

    VII. .

    . .

    1. .

    CH3 C

    O

    CH3 + NaO H3 NaIO + CHI3 + CH3COONa + 3NaOH

    I2 + NaOH NaOI + NaI + H2O

    3 NaIO + CHI3 + HCOONa + 2NaOH CH3-CHO

    C

    O

    H

    C6H5 C

    O

    OK

    C6H52 + KOH + C6H5CH2OH

    C6H5C

    O

    H

    C6H5C

    O

    OH

    KMnO4

    H+

  • 18 ) :

    2-3 , .

    ) : 2-3

    1%- ( ) 10%- . , .

    2. .

    2.1. . ) :

    2-3 50%- . , .

    2CH3COOH + Mg Mg(CH3COO)2 + H2 2CH3COOH + Zn Zn(CH3COO)2 + H2

    ,

    . ) :

    2-3 . ( ).

    2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O

    )

    : 20-30 , 0,5 2%- (III). (III), - .

    3CH3COONa + FeCl3 Fe(CH3COO)3 + 3NaCl

    , , - .

    C

    O

    ONa

    CH3 C

    O

    OH

    CH3+ H2SO4 + NaHSO4

    C17H35COONa + H2SO4 2C17H35COOH + Na2SO4 ( )

  • 19 Fe(CH3COO)3 + H2O Fe(OH)2(CH3COO) + 2CH3COOH

    )

    : 0,5 , , . .

    2RCOONa + CaSO4 (RCOO)2Ca + Na2SO4 RCOONa + (CH3COO)2Pb (RCOO)2Pb + 2CH3COONa

    2.2. .

    : 0,5 . 5-7 . H2SO4 ( .) , :

    . .

    ) : 1-2 . CaCl2. .

    HOOC COOH + CaCl2 Ca(COO)2 + 2HCl

    ( ) .

    10%- HCl, . , .

    Ca(COO)2 + 2HCl HOOC COOH + CaCl2

    ) : , , 1-2 , H2SO4 0,5 2%- K nO4. 0,5 . . .

    C

    O

    O

    CH3

    C2H5

    CH3COOH + C2H5OH + H2OH2SO4, to

  • 20

    . , .

    1. . , 0,5

    10%- NaOH . .

    C6H5COOH + NaOH C6H5COONa + H2O

    1%- FeCl3.

    (III): C6H5COONa + FeCl3 FeOH(C6H5COO)2 + 3NaCl

    (III)

    2. . ) (0,1-0,2 )

    , . , , . .

    ) 1-2 .

    . .

    HOOC COOH CO2 + HCOOH CO2 + CO + H2OKMnO4H2SO4

    to

    BaCO3 + H2OBa(OH)2 + CO2

    C

    CO

    O

    O

    O HC

    COH

    O

    O

    -H2O

    t

  • 21 3.

    .

    . (0,5-1 ) 2-3 FeCl3. :

    4. .

    0,5 (15%- ), 5%- . . 5%-

    . , ( ).

    5. .

    , , 2-3 0,5 H2SO4 , . : . , .

    OH CHCHOH

    COOHCOOH

    OH CH

    CHOH

    COOK

    COOH

    OH CHCHOH

    COOKCOOK

    KOHKOH

    O HC

    OH

    O

    C

    O

    O

    H

    O

    O C O

    O

    Fe

    O

    H

    C

    O

    3HCl ++ FeCl3

  • 22

    6. .

    3-5 , 0,5 , 1-2 3-5 . . , , 1-2 FeCl3. .

    . .

    1. .

    1 1 ,

    .

    2. .

    CH2COOHCOH COOH

    CH2COOH

    to

    (H2SO4)

    -

    CH2COOH

    C O

    CH2COOH

    + CO + H2O

    CO(CH2COOH)2 (CH3)2CO + 2CO2to

    CO2 + Ca(OH)2 CaCO3 + H2O

    CH3 (CH2)7 CH CH (CH2)7 COOH + Br2CH3 (CH2)7 CH CH (CH2)7 COOH

    Br Br

    [NH2OH] NH2OH + NaCl + H2O

    CH3 CO

    OC2H5

    + NH2OH + C2H5OHCH3 CO

    NHOH

    HCl + NaOH.

    CH3 CO

    NHOH( H3C C

    O

    NHO+ FeCl33 )3Fe + HCl

  • 23 0,5 1-2

    , .

    VIII. .

    . . 1. .

    1 .

    10 %- HCl, 10 %- H2SO4. , .

    C6H5NH2 + HCl [C6H5NH3]Cl

    C6H5NH2 + H2SO4 [C6H5NH3]2SO4

    2. .

    1 1 , . .

    3. .

    1 1 , 1

    CH2CH

    CH2

    O

    O

    O

    CO

    COCO

    (CH2)7(CH2)7(CH2)14

    CH

    CH3

    CH

    CH

    CH

    (CH2)7(CH2)7

    CH3CH3

    2Br2CH2CH

    CH2

    O

    O

    O

    CO

    COCO

    (CH2)7(CH2)7(CH2)14

    CHBr

    CH3

    CHBr

    CHBr

    CHBr

    (CH2)7(CH2)7

    CH3CH3

    NH2

    OH

    NO2

    NO2O2N N

    H

    H

    OH

    NO2

    O2N NO2

    +C2H5OH

  • 24 . .

    4. .

    1 2-3 , , 0,5 0,5 . , . .

    . .

    1. . ) : 1

    2 . : , , .

    ) : 1) : 0,2

    1 1 . .

    2) : 1

    1 , . .

    NH2 NH2Br Br

    Br

    + 3Br2 + 3HBr2

    2,4,6-

    CNH2 NH2O

    CNH2 NH3 OOC

    O

    COOHC COH

    OO

    OH

    + -+

    CNH2 NH2 + HNO3O

    CNH2 NH3 NO3O

    + -

    NH2 C

    O

    NH2-2NH3

    + 2H2O OH C

    O

    OH CO2-2H2O

    CO2 + Ba(OH)2 BaCO3 + H2O

  • 25 ) : 1

    5-7 10 %- 3-5 H2SO4 ( .). .

    ) : 1-2

    . , , , . , (1 ), 10 %- NaOH 2 %- CuSO4. ( ), .

    CNH2 N

    OCO

    NH2H

    CNH2 NOH

    CO

    NH2

    2. . ) : 1) 1 1 10 %-

    . .

    2) 1 1

    . , .

    H2SO4 + NaNO2 HNO2 + NaHSO4

    CNH2 NH2O

    + 2HNO2 CO2 + N2 + 3H2O

    CH3 CO

    NH2

    + H2ONaOH

    + NH3CH3 CO

    ONa

    CNH2 NH2O

    CNH2 NH2O

    CNH2 NH

    O

    C

    O

    NH2 + NH3+to

    CN O H

    NH2

    C NH2OO H

    Cu

    OH

    CNH2 O

    NC

    NH2OH

    CNH2 O

    NC

    NH2O

    CuCN O

    NH2

    C NH2O+ +-2H2O

  • 26

    ) : 1

    1 . , 2-3 ., , . .

    . .

    ) : 0,5 , . ( ). .

    NH2CH2COOH N+H3CH2COO-

    ) : 2 .

    2 .

    . , ....

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