1. .. 10 . 10 : . . / .. , .. , .. , .. ; . .. . 3- ., . .: , 2002

2. 1. . 1. .. . 2. , vita . ; 1824 . , 1828 . , 1845 . , 1854 . . 3. . , . : . 4. , , . 5. , , . , , . , , .. , , , . 6. (, ) () (, ) (, ) (, (, ) ) (, , (, ) ) 7. , , . 2

3. 2. .. 1. , , - , , , . : 1853 . . 1858 . , , . 1860 . . 2. , : 1. . 2. . : . : 1. , . 2. , , , . 3. , , , , . , , , . 3. : 1s22s12p3 2p 2s 1s 4 4 , .. . 3

4. 4. , .. ( , ). 5. : Br OH + Br2 ; OH +3Br2 + 3HBr Br Br : 25 + NaOH OH ONa + NaOH + H2O : Na2SO3 + H2SO4 Na2SO4 + H2O + SO2 Na2SO4 + H2SO3 6. , . , . 1828 . , , , . 7. . 3. 1. : 12 1s22s22p2, , 1- 6 4

5. s- (1s2), 2 s- 2 - (2s22p2). 2p 11 1s22s22p1 5 9 1s22s2 4 2s 1s 2s 1s 2s 1s 7 Li 1s22s1 3 2. ) ) 23 Na 11 24 Mg 12 2p ) 19 9F 2s 16 O 8 2p 2s 1s 1s22s22p4 ) 1 H 1s1 1 2p 2s 1s ; 1s22s22p6 2p 2s 1s 3s 1s22s22p63s2 2p 1s22s22p5 23 Na + 11 ; 2s 1s 24 Mg 2 + 12 ; 1s ) 3s 3s 1s22s22p63s1 19 9F ; 3s 1s22s22p6 2p 2s 1s 1s22s22p6 2p 2s 1s 16 2 2 2 6 8 O 1s 2s 2p ; 1H+ 1 1s0 ; 2p 2s 1s 1H 2 1s 1 3. 1s22s22p6 (Ne), O2, F, N3, Na+, Mg2+, Al3+. 2FNe Na+ Mg2+ 2s 1s 4. F2 14,2102 , 2 7,4102 . ( 2 ) , 2 s ( ), F2 - ( ). 5. N2 F2 , N2 , F2 , NN 941 /, FF 154 /. 5

6. 4. 1. 3 : sp3, sp2 sp-. 2. H H 1 C 2 C 3 C H 4 H C H H : 1,3-sp2- 2-sp- 4-sp3-. 3. sp- 2 , sp2- 1 , sp3 . 4. ) sp2- 120; ) sp- 180; , 2 , 3 ) sp- - 90; , 2 , 2 3 ) sp - 10928; 0,608 . ) 90; 6

7. 1. 5. 1. )CH2 ) 323 ; CH2 ) 32 CH ; O )CH3 CH2 C H ) CH3NH2 ; ) CH3CH2NO2 O ) CH3 C OH CH3 )CH C 3 ) ) N O ) CH3 C O C2H5 2. : ) () 32 O ) ) O C ( ) O CH3 C H ) C O CH3 C O CH3 C CH3 ( ) OH OH ) 33 O CH3 C O CH3 7

8. ) NO2 () CH3NO2 ) O N H 3. : CH3CH2NO2 CH3CH2CH2NH2 4. 612, , CH2 CH CH2CH2 CH2 CH3 11 ( ) CH2 CH CH2 CH CH3 CH2 CH CH CH2 CH3 CH3 CH3 3 1 4 1 CH3 CH2 C CH CH3 CH3 C CH CH3 CH3 2,3 1 CH3 3,3 1 CH3 CH CH CH2 CH2 CH3 CH3 CH2 CH CH CH2 CH3 CH3 CH CH CH CH3 2 3 CH3 CH2 CH CH3 4 2 CH3 CH2 CH2 C CH2 C CH3 CH3 2 2 CH3 CH C CH2 CH3 CH3 CH3 2 1 3 2 CH3 C C CH3 CH3 CH3 8 CH2 2,3 2

9. 5. O CH3 C H 6. 1. ) 3223 - ) CH3 CH CH2 CH3 2- 1 2 3 4 CH3 1 2 3 4 3 4 ) CH3 CH CH2 CH3 1 Cl 2 ) CH3 CH 3 ) CH C 3 1 2 2- CH CH3 -2 CH 3 4 2 1 ) CH3 CH CH2 CH3 -2 OH 4 3 O ) CH3 CH2 CH2 C 2 H 1 ) CH3 C O OH 2. ) 2- CH2 CH CH3 ) H3C CH CH2 CH2 CH3 ) -1 CH 1 CH3 C CH2 CH2 CH3 2 ) -2 CH3 C 3 4 5 C CH2 CH3 ) -2 CH3 CH CH3 ) -1 CH2 CH2 CH3 OH ) CH3 CH2 C OH ) CH3 CH2 C O H O OH 9

10. 7. 1. 2. , , . , , , . 3. ) CH3 CH3 CH CH CH3 1) CH3 CH3 2,3- CH3 C CH2 CH3 CH3 2,2- 322223 - 2) CH3 CH2 CH CH3 CH3 2- CH3 32223 - CH3 C CH3 CH3 2,2- ) : 1) 322223 - 32223 - 10

11. CH3 CH3 2) CH3 C CH2 CH3 CH3 C CH3 CH3 2,2- CH3 2,2- 4. , , , .. CH3 CH3 H C C H CH3 --2 C H H --2 H H CH2 C CH2 C CH3 C CH2 C CH3 CH3 CH2 C H -1,2- CH3 H CH3 -1,2- 5. * CH3 CH CH2 CH3 OH , .. CH3 CH3 H C2H5 HO OH H C2H5 6. : ) 614 CH3 CH2 CH CH2 CH3 322223 CH3 CH3 CH3 C CH2 CH3 CH3 CH CH CH3 CH3 CH3 CH3 ) 38 , , 322 CH3 CH CH3 OH 323 11

12. ) 410 , , : 3222 CH3 CH CH2 OH CH3 CH2 CH CH3 CH3 OH 3223 3223 ) 48 , , , . CH2 CH CH2 CH3 CH2 C CH3 CH3 CH CH3 CH3 C CH3 CH CH3 CH3 H CH3 C C C H CH3 H H ) C4H9Cl , CH3 CH CH2 Cl CH3CH2CH2CH2Cl CH3 CH3 CH2 CH Cl CH3 7. : O CH3 | 3 l | CH3 O 1) CH3 CH2 C CH3 C CH3 H 2) 322 -1 CH3 CH CH3 -2 323 3) CH3 C O OH O CH3 O CH3 CH2 C OH 12

13. 2. 8. 1. ) ; ) ; ) ; ) ; ) ; ) ; ) . 2. ) : CH4 + Cl2 CH3Cl + HCl t C2H6 CH2 CH2 + H2 Al2O3 H3 CH3 CH2 CH2 CH3 t AlCl3 CH3 CH2 CH CH3 CH3 ) : Pt CH2 CH2 + H2 C2H6 CH2 Pt CH + H2 AlCl3 CH2 CH CH2 CH3 CH3 CH CH CH3 t 3. , ; , CH2 CH CH3 CH2 CH2 CH3 AlCl3 t CH3 CH CH3 CH3 4. ) ; ) ; ) ; ) . 13

14. 9. . 1. , . . , , .. . - . 2. , , , .. ( +). , , , (CH3O-, Cl-, OH-). 3. -, , -, . , . 4. ) CH 3 Cl , , , .. CH3 . CH3 ) CH3 , .. , I , CH3 +I . ) CH3 O C OH CH3 +I , O H, , , , HCOOH. ) CH3 CH CH2 , CH2 CH2 , .. CH3 +I . 14

15. ) CH3 OH O H , , , .. CH3 +I . CH3OH + NaOH C6H5OH + NaOH C6H5ONa + H2O Kg (CH3COOH) = 1,7510-5 Kg (HCOOH) = 1,710-4 CH3 + NaOH OH Cl + NaOH + NaCl 10. 1. : ( , 5 ); ( ); ( ). , , .. . 2. , , . , .. . 3. , . , , . , , . 4. , , : , , , ; . 15

16. 5. , . C4H10 C2H6 + C2H4; C8H18 C4H10 + C4H8; C16H34 C8H18 + C8H16 6. , , , , . , . 7. , .. : . , 6 . . 8. , . 2C2H6 + 7O2 4CO2 + 6H2O CH4 + 2O2 CO2 + 2H2O 2C4H10 + 13O2 8CO2 + 10H2O C3H8 + 5O2 3CO2 + 4H2O 2C6H14 + 19O2 12CO2 + 14H2O C5H12 + 8O2 5CO2 + 6H2O 9. 2CH4 t C2H2 + 3H2 3 C2H2 C t 10. . : (H2, CH4, CO, CO2, NH3, N2); ( , (NH3, H2S, C6H5OH), (). NH3 + HCl NH4Cl 2H2 + O2 2H2O H2S + PbO PbS + H2O N2 + 3H2 2NH3 11. , , , . 16

17. 3. 11. 1. CnH2n+2 2. 614 : 322223 CH3 CH CH2 CH2 CH3 - CH3 2- CH3 CH CH CH3 CH3 CH2 CH CH2 CH3 CH3 3- CH3 CH3 2,3- CH3 CH3 C CH2 CH3 CH3 2,2- 3. , . , , . 4. : 38 (), 36 (), 410 (), 24 (), 48 (), 26 (), 4 (), 510 (). 5. 1) Cl2 3) Br2 2) Na ) C2H6 B A 1) 26 + Cl2 C 2 H 5 Cl + HCl 2) 2C2H5Cl + 2Na CH3CH2CH2CH3 + 2NaCl 3) C4H10 + Br2 C 4 H 9 Br + HBr ) CH3CH2CH2CH3 1) Al2O3 450 C A 2) Br2 17

18. Al2O3 450 C 1) CH3 CH2 CH2 CH3 CH3 CH CH3 CH3 Br 2) CH3 CH CH3 + Br2 CH3 C CH3 + HBr CH3 CH3 2--2- 6. CH3 CH3 C CH3 2,2- CH3 CH3 CH3 CH3 C CH3 + Br2 CH3 C CH2Br + HBr CH3 CH3 7. 0,1 C n H 2n + 2 1. n(O2) = 0,5 3n + 1 + O2 nCO2 + (n + 1)H2O 2 V = 11,2 : 22,4 / = 0,5 Vm 0,1 2 0,5 0,1 0,5 = , 0,3n + 0,1 = 1, n = 3 , = 3n + 1 1 3n + 1 1 2 C3H8 ;323 : 323 (). 2. 8. 1 .. 22,4 , , : 22,4 5,6 11 22,4 M 11 22,4 = ;M= = 44 5,6 11 5,6 38 323 : 323 (). 18

19. 9. . , . 10. . O 4 + 2 H C + 2 24 + 2 23, H 11. x 2 x y 3 y 2C 2 H 6 + 7O 2 4CO 2 + 6H 2O ; C3H8 + 5O 2 3CO 2 + 4H 2O 120 120 =1,2 . 100 n(C6H6) = x , n(C3H8) = y , ( x + y) 22,4 = 10,08 ; x = 0,6 - 1,5y; 0,6 - 1,5y + y=0,45; : 2x + 3y = 1,2 0,5y = 0,15; y = 0,3; x = 0,15; V(C2H6) = nVm = 0,1522,4=3,36 ; V(C3H8) = nVm =0,322,4 = 6,72 . : V(C2H6) = 3,36 ; V(C3H8) = 6,72 . 12. . 2 (.. , ) Mr = D(26) M(C2H6) = 1,808 30 = 54,24 ( (612) 72) , . ( - -, , 2 ). H3CH2CH3 + Br2 CH3CHCH3 + CH3CH2CH2Br Br CH3CH2CH2 CH3 + Br2 CH3 CH2 CH2 CH2Br+CH3 CH2 CHBrCH3 , (1 ). 44 + 58 (1 ) = 54,24; 14 = 3,76; = 0,269; 1- = 0,731. . : W (410) = 73,1% CO 2 + Ca (OH ) 2 CaCO 3 + H 2O ; n(CO2)=n(CaCO3)= 12. () 1. , , . -1 : H3 CH CH CH2 CH3 H3 C CH CH3 CH3 19

20. CH3 CH3 CH3 CH3 CH3 CH3 C2H5 C C2H5 CH3 C H H H C H3 C H C2H5 H2 = C CH2 CH3 CH3 CH2 CH CH CH3 2. ) : Cl Cl CH2 C CH3 + Zn CH3 Cl C CH3 + ZnCl2 CH2 1,2--2- t CH3 C CH3 + NaOH CH3 CH2 2--2- CH3 C CH3 + NaCl + H2O CH3 Cl t CH2 CH CH3 + NaOH CH3 CH2 1--2- CH3 CH CH3 CH3 Al2 O3 t CH2 C CH3 + NaCl + H2O CH3 C CH3 + H2 CH3 OH CH3 C CH3 CH3 20 t H2 SO4 CH2 2--1 C CH3 + H2O CH3

21. t H2 SO4 CH3 CH CH2 OH CH3 CH2 C CH3 + H2O CH3 2--1 ) -2 : CH2 CH CH2 CH3 Al2O3 -1 CH3 CH CH CH3 Br CH3 CH CH2 CH3 + NaOH CH CH3 + NaBr + H2O CH3 CH t 2- CH3 CH CH CH3 + Zn Cl t CH CH3 + ZnCl2 CH3 CH Cl 2,3- t CH3 CH2 CH2 CH3 CH3 CH Ni CH CH3 + H2 t C8H18 CH3 CH = CH CH3 + CH3 CH2 CH2 CH3 ) -1 : CH3 CH CH CH3 Al2O3 CH2 CH CH2 CH3 -2 CH2 CH2 CH2 CH3 + NaOH Br t CH2 Cl t CH CH2 CH3 + NaBr + H2O 1- CH2 CH CH2 CH3 + Zn CH2 Cl CH CH2 CH3 + ZnCl2 1,2- CH3 CH2 CH2 CH3 t Ni CH2 = CH CH2 CH3 + H2 C8H18 t CH2 CH CH2 CH3 + CH3 CH2 CH2 CH3 21

22. 3. )CH3 CH2 CH CH2 1) HCl A 1)CH CH CH CH + HCl 3 2 2 3) KMnO4 2) KOH B H2O CH3 CH2 CH CH3 Cl 2- 2) CH 3 CH 2 CH CH 3 + KOH t t Cl CH CH3 + KCl + H2O CH3 CH -2 3) 3 CH3 CH CH CH3 + 2KMnO4 + 4 H2O 3CH3 CH CH CH3 + 2MnO2 + 2KOH OH OH 2,3- ) CH3 CH2 CH2 CH2Br 1) KOH 1) CH3 CH2 CH2 CH2 Br + KOH CH3 CH2 CH 2) HBr A CH2 + KBr + H2O -1 2) CH3 CH2 CH CH2 + HBr CH3 CH2 CH CH3 Br 4. CH3 CH2 CH2 Cl CH3 CH CH3 Cl 1) CH3CH2CH2Cl + KOH CH3CH 2) CH3 CH CH2 + HCl 5. CH2 + KCl + H2O CH3 CH CH3 Cl HBr. C2H6 + HBr C2H 4 + HBr CH3 CH 2 Br HBr, CH3 CH2Br . 22

23. 6. , , , . C2H4 + Cl2 CH2Cl CH2Cl; 24 + HCl CH3CH2Cl; C2H4 + H2O CH3CH2OH; C2H4 + H2 CH3CH3; 3C2H4 + 2KMnO4 + 4H2O 3CH2CH2 + 2MnO2 + 2KOH; OH OH C2H4 + Br2 CH2Br CH2Br. 7. nH2n + H2 CnH2n+2 V(CnH2n)= V(H2)= 0,896 1 .. 22,4 , , : 22,4 ; 0,896 2,8 22,4 2,8 22,4 ,= = 70 = 0,896 0,896 2,8 510 (5 12 + 10 = 70) : Mr = 70, CH2 CH CH2 CH2 CH3 (-1) CH CH2 CH3 (-2) CH3 CH 8. 20 Cn H 2n + 22,4 90 3n 2 O2 nCO2 + nH2O 33,6n 3n = 33,6n 2 V(CnH2n) = Vm n = 22,4 / 1 = 22,4 90 22,4 20 90 2. = 3 = 3 C3H6 = ,n= 20 33,6 22,4 33,6n : 36 . 1. V(O2) = Vm n = 22,4 / 9. 25, 4 43, 2 Cn H 2 n + Cl 2 Cn H 2 n Cl 2 ; C n H 2 n + Br2 C n H 2 n Br2 y (12n + 2n + 71) = 25,4; 14ny = 25,4 71y; y (12n + 2n+160)=43,2 14ny = 43,2-160y; 17,8 = 89y; y = 0,2; n = (25,4 - 710,2)/40,2=11,2/2,8=4 C4H8 CH3 CH 2 CH = CH 2 23

24. CH3 C CH2 CH3 CH = CH CH2 CH3 : C4H8. 13. 1. , . . 2. 58 : CH C CH2 CH2 CH3 CH C CH CH3 CH3 CH3 C C CH2 CH3 3. t CaC2 + CO , 2 + 22 ()2 + 22 1. CaO + 3C t 1500 C CH4 2CH4 2. C + 2H2 C2H2 + 3H2 , 4. 2) Br2 1) H2,Pt 3) KOH ) C3H4 B A Pt CH2 CH CH3 1) HC C CH3 + H2 2) CH CH CH CH CH CH + Br 2 3 2 2 Br 3 Br 1,2- 3) CH2CHCH3 + 2KOH CH CCH3 + 2KBr + 2H2O Br Br ) C3 H 4 2) Cl2 1) H2 (2 ) A Pt 1) CH C CH3 + H2 CH2 CH CH3 + H2 Pt Pt CH2 3) KOH CH CH3 CH3 CH2 CH3 2) 323 + Cl2 C3H7Cl + HCl 24 B

25. 3) C3H7Cl + KOH CH2 CH CH3 + KCl + H2O 2) C )CaC2 1) H2 O 400 C A 3) CuCl, t 1) 2 + 22 ()2 + 22 ; 3) 2C2H2 CuCl HC t CH CH3 + Br2 CH3 C 2) CH3 CH CH CH3 + 2KOH Br C CH3 CH3 CH CH CH3 Br 400 C CH CH2 -1--3 () 5. CH3 CH CH CH3 1) CH3 CH C 2)3C2H2 Br Br CH3 C H C CH3 + 2KBr + 2 2O 6. , . 7. C3H8 + 5O2 3CO2 + 4H2O; 2C3H6 + 9O2 6CO2 + 6H2O C3H4 + 4O2 3CO2 + 2H2O V(CO 2 ) 4,03 Ar(C) = 12 = 2,159 m(C)=n(C)Ar(C)= Vm 22,4 m(H)=2,48 - 2,159=0,321 (); m(H2O)= 18 0,321 = 2,89 () 2 : m(H2O) = 2,89 . . . 4,03 4,03 8. x x x C n H 2n + Br 2 C n H 2n Br 2 25

26. y 2y y C n H 2n 2 + 2Br2 C n H 2n 2 Br 4 160( x + 2 y) = 40 ( x + y)22,4 = 3,92 (14n + 160) x + (14n + 318) y = 47,2 x + y = 0,175; 0,175 y + 2y = 0,25; y = 0,075; x = 0,1 (14n+160)0,1+(14n+318)0,075=47,2; 1,4n+16+1,05n+23,85=47,2 2,45n = 7,35; n = 3 0,075 0,1 = 0,43 = 0,57 ; (C3H4)= (C3H6)= 0,175 0,175 : (C3H6) = 0,57, (C3H4) = 0,43. 14. 1. : 1) CH2 CH CH CH2 -1,3 2) CH2 C CH2 3) CH2 CH CH2 CH -1,4 CH2 2. 610 : CH2 CHCHCH CH2 CH CH2 CH2 CH CH2 CH2 CH3 CH2 CCH2CH CH2 CH2 CH2 CH3 CH3 CH3 CH2 CC CHCH2CH CH CH3 CH2 CCH CH CH3 CH3 CH2 CH2 26 CHC C CH CH3 CH3 CH CH2 CH2 CH3 CH2 CHCH CH3 CH C CH CH CH2CH3 CH2 CH3

27. CH3 CH C C CH3 CH3 CH = CH CH = CH CH3 CH3 3. --. CH3 CH3 CH CH2 CH CH CH C CH2 CH2 CH3 CH2 CH C H H 4. CH2 CH CH CH2 + Br2 C CH C C CH2 H CH3 H CH2 CH CH CH2 Br Br CH2 CH CH CH2 1,4--2 CH2 CH CH CH2 + Br2 3,4--1 Br Br 5. ) ClCH2CH2CH2CH2Cl 1) KOH 2) 2CH2 CH2 CH CH CH2 + 2HCl CH CH3 + CH3 CH CH Cl 1--2 )2222 CH2 CH2 Cl 3--1 1) H2SO4 180 C 1) 2222 180 C HCl + 1 CH CH CH2 + 2KCl + 2H2O -1,3 CH2 CH H2SO4 2) 1) ClCH2CH2CH2CH2Cl + 2KOH A A Br2 3) Br2 + 1 2) H2SO4 180 C CH CH CH2 + 2H2O -1,3 27

28. 2) 2CH2 CH CH CH2 + 2Br2 CH2 CH CH CH2 + CH2 CH CH CH2 Br Br Br Br 1,4--2 3,4--1 CH2 CH CH CH2 3) CH2 CH CH CH2 + Br2 Br Br CH2 CH CH Br Br Br Br Br 1,2,3,4- CH2 CH CH CH2 CH2 + Br2 Br Br Br Br Br 1,2,3,4- 6. CxHy+O2 CO2 + H2O; m(C) = 8,96 2 12 = 4,8 ; m(H) = 5,4 = 0,6 22,4 18 4,8 0,6 = 0,4 : 0,6 = 4 : 6 = 2 : 3 : 12 1 27 n 0,1 8,96 3 C2H3 + O 2 2CO 2 + H 2O ; 2 22, 4 27 x : y= 2,7n 8,96 27 44,8 n= 27 8,96 =2 44,8 2,7 C4H6 ;CH2=CH-CH=CH2 . : CH2=CHCH=CH2. 15. 1. ) + Br2 Br CH2 CH2 CH2 Br Br ) + HBr + Br2 2. H H C2H5 H -1--3- 28 CH3 CH3 ) H C2H5 -1--3-

29. H CH3 H CH3 CH3 CH3 ) H H -1,2- -1,2- 3. 714 C2H5 , : C2H5 , : H3C CH2 CH3 CH CH2 CH2 CH CH3 5--1, : CH3 CH3 CH2 CH CH CH2 CH2 CH3 -3, : 4. Mr(/)=282=56. .. , , . nH2n 14n=56; n=4 .. 2- , CH3 : CH3 16. () 1. H3C CH3 C2H5 C2H5 CH3 CH3 CH3 C2H5 C3H7 CH3 H3C CH3 CH3 3 C3 3 CH3 CH3 29

30. 2. - : CH3 C2H5 CH3 3. CH3 CH3 FeCl3 + Cl2 + Cl - CH3 + Cl2 CH3 Cl n- CH2Cl + HCl 4. CH3 + HNO3 CH3 CH3 H2SO4 + NO2 O2N - - CH3 COOH + 3[ O ] + H2O 5. x + Br2 FeBr3 Br 224 + HBr 1. m(C6H6) = M(C6H6) n = 78 / 1 = 78 V(HBr) = Vn n = 22,4 / 1 = 22,4 x 2. + Br2 FeBr3 Br 224 + HBr 22,4 78 224 224 78 = ;= = 780 (66). : m(C6H6) = 0,78 . 78 22,4 22,4 30

31. 6. 1) + 3H2 CH3 2) Pt + 3H2 Pt CH3 3) C6H12 + H2 Pt C6H14 1. m(66) = 0,25 100 = 25 ; m(78) = 0,15 100 = 15 m(612) = 0,25 100 = 25 2. m(66) = (66) n = 78 / 1 = 78 m(78) = (78) n = 92 / 1 = 92 ; m(612) = (612) n = 84 / 1 = 84 V1(H2) = Vm n1 = 22,4 / 3 = 67,2 V2(H2) = Vm n2 = 22,4 / 3 = 67,2 V3(H2) = Vm n3 = 22,4 / 1 = 22,4 15 25 x Pt Pt C7H8 + 3 H2 C7H16 + 3 H2 C6H6 C6H14 ; 92 67,2 78 67,2 25 z Pt C6H12 + H2 84 22,4 C6H14 25 67, 2 25 = ,= 21,5 (2) 78 78 67, 2 y 67, 2 15 25 z 25 22,4 15 ,y = 11,0 (2); ,z= 6,7 (2) = = 84 92 92 67, 2 84 22, 4 4. V(2) = V1 + V2 + V3 = 21,5 + 11,0 + 6,7 = 39,2 . : V(H2) = 39,2 . 3. 7. x 15,6 1. + HNO3 H2SO4 NO2 + H2O m(66) = (66) n = 78 / 1 = 78 m(65NO2) = (65NO2) n = 123 / 1 = 123 x 15,6 2. + HNO3 78 H2SO4 NO2 + H2O 123 15,6 123 15,6 = ,x= = 24,6 (65NO2) 78 123 78 3. m(65NO2) = 0,7 24,6 = 17,22 . : m(65NO2) = 17,22 . 31

32. 8. CH2 C CH , , , , .. , . CH2 C CH CH2 + [Ag(NH3)2]OH CH2 C CH CH2 C CH CH2 + 2Br2 COOH + [O] 9. C+2H2 CH4 t0 2CH4 C2H2+3H2 C t 3 C2H2 0 t 2CH4 C2H2+3H2; C+2H2 CH4; 3 C2H2 C t ; AlCl 3 + 24 23 32 t0 Ni 22+2 24; t 0 ,Ni 23 2 C CBr2 +2CO2 C Ag CHBr2

33. 4. 17. 1. , , . : 1) ; 2) ; 3) , . -2 , , . -3--1 , , . -4--1,2 , . 2. H3 CH CH2 CH3 H2 CH2 CH CH2 OH OH -3--1 -2 H2 CH CH2 CH OH CH2 OH -4--1,2 3. , .. , , , , .. , , .. . 4. 512 8 : 32222 -1 H3 CH2 CH2 CH OH -2 CH3 H3 CH2 CH CH2 OH 2--1 CH3 H3 CH CH2 CH2 OH 3--1 CH3 CH3 H3 CH2 C OH 2--2 CH3 33

34. CH3 H3 C CH2 OH 2,2--1 CH3 H3 CH CH CH3 3--2 CH3 OH H3 CH2 CH CH2 CH3 -3 OH , : 32223 32223 5. OH CH3 CH CH CH3 CH3 C CH3 CH3 OH CH2 CH2OH CH3 CH CH CH3 OH C2H5 2--1 3--2 CH3 CH OH -2,3 CH3 2--2 CH CH2 OH -2--1 6. HC C CH CH OH C CH2CH3 CH3 5--4--1--3 812. () 18 . . 7. 2,6, 2,15, 3,5. , 0,9, 1,35, . 34

35. 8. 2CH3OH + 2Na 2CH3ONa + H2 CH3 CH3 2CH3 C CH3 + H2 2CH3 C CH3 + 2Na ONa OH , .. , 2--2. , 3 , 2--2 . , . 9. 2CH3 CH CH3 + H2 2CH3 CH CH3 + 2Na ONa OH + CH3 CH CH3 + HBr H CH3 CH CH3 + H2O OH Br 2- 10. CH3 CH2 CH2 OH + CuO t O CH3CH2 C CH3 CH CH3 + CuO OH t H + H2O + Cu CH3 C CH3 + H2O + Cu O 11. CH2 CH CH3 + 2H2O Cl Cl CH2 CH CH3 + 2HCl OH OH -1,2 CH2 CH CH3 + H2O CH2 CH CH3 + HCl Cl Cl OH 1--2 Cl CH2 CH CH3 + H2O CH2 CH CH3 + HCl Cl OH Cl 2--1 Cl 35

36. 12. Pt CH CH2OH + H2 CH2 CH3 CH2 CH2 OH -1 + CH2 CH CH2OH + H2O H CH3 CH CH2 OH OH -1,2 CH2 CH CH2OH + Cl2 CH2 CH CH2OH Cl Cl 2,3--1 CH2 CH CH2OH + HCl CH3 CH CH2OH Cl 2--1 13. CH2 OH CH OH + CH3COOH O H+ CH2 OH CH2 OH CH OH + 2CH3COOH CH2 OH CH2 OH CH OH + 3 CH3COOH CH2 OH O CH2 O C CH3 O CH O C CH3 + 3 H2O O CH2 O C CH3 H+ CH2 O C CH3 CH OH CH OH 2 O CH2 O C CH3 CH OH + 2 H2O O CH2 O C CH3 O CH2 O C CH3 O H+ CH O C CH3 + 3 H2O O CH2 O C CH3 CH2 OH CH OH + 3CH3C CH2 OH 14. x 8,96 2 (14 n +18) 22, 4 2Cn H 2 n +1OH + 2 Na 2Cn H 2 n +1ONa + H 2 36 + H2O O OH

37. x 56 (14 n +18) 14 n Cn H 2 n +1OH Cn H 2 n + H 2O 22,4x=8,962(14n+18); x=0,8(14n+18) 14nx=56(14n+18); 14n0,8(14n+18)=56(14n+18) 11,2n=56; n=5 C5H11OH CH3CH2CH2CH2CH2OH CH3 CH CH2 CH2OH CH3 CH2 CH CH2OH CH3 CH3 CH3 CH3 C CH2 CH2OH CH3 CH2 CH2 CHCH3 OH CH3 CH3 CH3 CH3 C CH2CH3 CH3 CH CHCH3 OH OH CH3 CH2 CH CH2CH3 OH 15. x 2Cn H 2 n +1OH + 2 Na 2Cn H 2 n +1ONa + x x 2 H2 nx Cn H 2 n +1OH + 1,5nO 2 nCO 2 + (n + 1)H 2O nx C4H9OH = 8 ; 2n=8; n=4 x 2 CH3 CH CH2CH3 ; : CH CH CH CH 3 2 3 OH OH 16. C2H5OH + HCl C2H5Cl + H2O 1. , . 2. , , H2SO4 3. , . 4. . 37

38. 18. 1. HO CH3 CH3 OH C2H5 OH 3- H3C 2,5- 4- 2. , , , , , . .. +I , . 2 , . 3. ONa OH + 2 + 2 O + NaCO3; OH + Na+ + H2O + CO2 O - + Na+ + CO3 OH + H2O + CO2 + CO3 . 4. OH OH H CH2 OH CH2 H + H H H + H C O H OH H H + H2O H 38

39. OH OH H OH CH2 OH CH2 CH2 H H2O H H OH H OH CH2 H H OH OH CH2 CH2 H + H H H H H C + H OH H H + O H2O H OH H OH CH2 OH CH2 H OH CH2 H H OH H OH H + nO (n+1) OH CH2 H OH H2 CH2 H OH CH2 H C + n H2O H H a 2C x H yOH + 2Na 2C x H yONa+ H a 2 H2 2Cn H 2n-7OH + 2Na 2Cn H 2n-7ONa+ n1 H ; 2 H2 a 0,168 =0,0075 ; + = 0,015 ; V(2) = + = 22,4 2 2 V(Br2) = (160 0,025 ) 160 = 0,025 . , . a 2 Cx H yH + Br2 = Cx H y Br2 OH ; 2n-7OH + 2Br2 =2Cn H 2n-9Br2OH+ 2HBr + 2 = 0,025; = 0,005; = 0,01 : 0,005 (12x +y + 17) + 0,01 (14x + 10) = 1,37 12x + y + 28x = 237; n (n 7) : = 3, y = 5; n= 7. : 35, 77. : W(C3H5OH) = (0,005 58) 1,37 =0,212 ; W(C7H7OH) = 1 0,212 = 0,788 39

40. 19. 1. 1 , 3. O CH3 C CH3 H C H O ( , , ) (, -2) 2. ) 2-; ) 3-; ) 3- 3. K : CH3 CH2 CH2 C O CH3 CH C H CH3 2- H - CH3 C CH2 CH3 O , : CH2 CH3 CH CH CH2 CH2 OH 3--1 CH2 CH CH2 OH 2--1 CH CH CH3 OH 3--2 CH3 CH2 CH2 C CH3 CH C CH3 O H + H2 O H + H2 Ni CH3 CH2 CH2CH2 OH -1 Ni CH3 CH CH2OH CH3 2--1 Ni CH3 C CH2 CH3 + H2 CH3 CH CH2 CH3 OH -2 O CH2 = CH CH2 CH2 OH + H2 Ni CH3 CH2 CH2 CH2 OH -1 40 O

41. CH3 CH = CH CH2 OH + H2 CH2 = CH CH CH3 + H2 Ni Ni CH3 CH2 CH2 CH2 OH -1 CH3 CH2 CH CH3 OH -2 OH 4. O 16 Ni + H2 CH3OH H O Vm n = 22,4 / 1 = 22,4 1. V HC H x HC m(CH3OH) = M(CH3OH) n = 32 / 1 = 32 O x 16 Ni 2. H C CH3OH + H2 22,4 H 32 16 22,4 16 ;= = 11,2 H C = 32 22,4 32 O H 11,2 298 V T V V = 12,23 H C 3. 1 = 2 ; V2 = 1 2 ; V2 = 273 T1 T2 T1 O : V1 H C H = 11,2 .. , V2 H C O H O H = 12,23 25 . 5. CH3 C CH3 + H2 Ni CH3 CH CH3 O OH M(C3H8O) = 312+81 + 116 = 60 /. : M(C3H8O)=60 / 6. O H C H O H C H O + Ag 2O H C + 2[Ag(NH3)2]OH O + 2Ag H O H C + 2Ag + 4NH3 + H2O OH H C OH , , O + Ag2O CO2 + H2O + 2Ag H C OH 41

42. 7. O Cn H2n+1 C H O + Ag2O + 2Ag Cn H2n+1 C OH 14n + 1 + 12 + 32 + 1 = 88; n = 3. . CH3 CH2 CH2 C CH3 CH C CH3 O + Ag2O H O + Ag2O H O CH3 CH2 CH2 C + 2Ag OH O CH3 CH C CH3 + 2Ag OH 2- 8. x CH3 C CH3C O + Ag2O H z O + KOH OH y CH3 C CH3C 0,54 + 2Ag OH O + H2O OK O 1. m(Ag) = M(Ag) n = 108 / 2 = 216 m(3) = M(3) n = 44 / 1 = 44 m() = M() n = 56 / 1 = 56 m(3) = M(3) n = 60 / 1 = 60 x CH3 C O H + Ag2O 44 y CH3 C 60 0,54 + 2Ag OH 216 O O 44 0,54 0,54 = 0,11 CH3C 2. ;= = 216 44 216 H y 0,54 60 0,54 ;y= = 0,15 (3) = 216 60 216 z 0,15 O CH3C + KOH OH 56 60 3. O CH3C OK + H2O z 0,15 ; z= 56 0,15 = 0,14 . : m(CH3CHO)=0,11, m(KOH)=0,14 . = 60 56 60 9. : 1. Cu(OH)2 ; , (Cu2O), , , . 42

43. O CH3 C H O t + 2Cu(OH)2 CH3 C OH + Cu 2O + 2H2O 2. ; , , , , . O CH3 C H O + Ag2O CH3 C 10. O CH 3 CH 2 C H + 2Ag O t +2Cu (OH )2 OH CH 3 CH 2 C OH + Cu 2 O +2H 2 O (I) : Cu(OH)2, Cu2O. 11. CxHyOz + O2 CO2 + H2O V 12 3,36 44 = 6,6 ; m(C) = 6,6 = 1,8 ; m(CO2) = M= Vm 44 22,4 m(H2O) = 2,7 1 / = 2,7 ; m(H) = 2 2,7 = 0,3 ; 18 m(O) = 4,5 1,8 0,3 = 2,4 . 1,8 0,3 2,4 CxHyOz ; x : y : z = = 0,15 : 0,3 : 0,15 = 1 : 2 : 1 : : 12 1 16 CH2O M D = ; - = 1,035 28,9 30 /; (2) = 30 / 2 . O , H C H , , .. , Formica Rufa . , , , . . 12. : O CH3 CH2 C H + Br2 O CH3 CH C Br + HBr H 2- 43

44. Br O CH3 CH2 C H + 2Br2 CH3 C C O + 2HBr H Br 2,2- O O CH3 CH2 C + Br2 CH2 CH2 C + H + HBr H H Br 3- - : O O H+ CH3 CH2 C + Br2 C3 CH C + HBr H H Br 13. CxHyOz + [O] R C O OH 14,8 R C (R+45) O + NaHCO3 OH 4,48 R C O + H2O + CO2 ONa 22,4 14,8 (-) 4,48 (CO2) (R+45) (-) 22,4 (CO2) 14,822,4 = 4,48(R+45); 14,8 = 0,2(R+45); R=74-45=29=C2H5 11,6 14,8 y 74 C x H yOz + [O] = C2H5COOH 11,6 (-) 14,8 (-) 11,6 74 ; y= = = 58 (-) 74 ( - ) 14,8 ( ) C2H5 C O H : C2H5 C O H 14. x H C 30 O + 4 [Ag(NH3)2]OH H y CH3 C 44 O + 2[Ag(NH3)2]OH H CO2 + 4 Ag + 3 H2O + 8 NH3 432 CH3COOH + 2Ag + 4NH3 + H2O

45. x + y = 1,18 432x 216 y 30 + 44 = 8,64 x+y=1,18 14,4x+4,9y=8,64 14,4x+4,9(1,18-x)=8,64; 14,4x+5,78-4,9x=8,64; 9,5x=2,86 x=0,3; y=0,88 0,3 =0,254 25,4 %; (CH3CHO)=74,6% (HCHO)= 1,18 20. 1. CH3(CH2)7 H C H O C (CH2)7C OH 2. C17H33COOH + H2 P, t O CH3 (CH2)16 C OH 3. 568 17 H35COOH + 262 182 + 18 2 1. m(C17H35COOH)=M(C17H35COOH)n=284 /1 =284 V(O2) = Vm n = 22,4 / 26 = 582,4 568 284 582,4 17 H35COOH + 26O 2 182 + 18 2 2. 568 568 582,4 = ;= = 1164,8 (2) = 1,165 3 284 284 582,4 1164,8 = 5546,67 = 5,55 3; 0,21 : V(O2) 1,165 3; V 5,55 3. 3. V = 4. 1735 + 262 182 + 18 2 1531 + 232 162 + 16 2 m(C17H35COOH)=m(C15H31COOH)=100;V(C17H35COOH)= 100 = 0,352 284 V(C17H31COOH)= 100 256 = 0,391 ; V1(O2) = 0,352 26= 9,152 ; V2(O2)= 0,391 23= 8,993 ; V(2) = (9,152 + 8,993) 22,4 = 406,4 ; 45

46. V() = 406,4/0,21= 1935 =1,94 3; V(CO2) = 0,352 18 + 0,391 16 = 12,6 ; V(CO2) = 12,6 22,4 = 282 ; V(2O)= V(CO2)= 12,6 ; m = (H2O)= 12,6 18 = 226,8 . : 1,94 3 ; 282 2; 226,8 2. 5. 1735 + 262 182 + 18 2 1531 + 232 162 + 16 2 1. M(C17H35COOH) = 284 /; M(C15H31COOH) = 256 / . 284 + 256 = 200, 540 = 200, = 0,37; 0,37 . 2. n1(O2) = 26 0,37 = 9,62 n2(O2) = 23 0,37 = 8,51 . n(2) = 9,62 + 8,51 = 18,13 V(O2) = Vm n = 22,4 / 18,13 = 406,112 V = 406,112 = 1933,867 1,934 3. : V = 1,934 3. 0,21 6. O O Fe2O3 + 6CH3C 2 CH3C OH O Fe + 3H2O 3 Fe2O3 + 6H+ 2Fe3+ + 3H2O O O Fe(OH)3 + 3CH3C CH3C OH O Fe + 3H2O 3 Fe(OH)3 + 3H+ Fe3+ + 3H2O , .. , (III), Fe2O3 Fe(OH)3 , . 7. NaHCO3 + CH3C O OH O CH3C ONa + H2O + CO2 , . 8. O CCl3C OH , O CHCl2C OH, O CH2ClC OH, O CH3C . 46 OH , O C2H5C OH

47. , , , Cl C C OH , , Cl . , , . Cl O Cl H O H C C Cl OH O C C H Cl OH , .. 25 +I , 3, .. . 9. , , : . H O O ; H C OH O + Ag2O CO2 + H2O + 2Ag 10. O 3 2Ck H2 k+1 C + Mg OH O 1. m CkH2 k+1 C 0,56 (Ck H2k+1 COO)2Mg + H2 O n=(14k+46) /2 =(28k+92) = M CkH2k + C OH OH V(H2) = Vm n = 22,4 / 1 = 22,4 0,56 3 2Ck H 2k+1COOH + Mg (CkH2k+1COO)2Mg + H 2 22,4 (28k+92) 2. 3 0,56 = ; 15,68k + 51,52 = 67,2; k = 1 28k+92 22,4 O CH3C O . : CH3C OH OH 47

48. 11. I. 1) 2CH3COOH + 2Na 2CH3COOHa + H 2 2) 2CH3COOH + Na2 2CH3COONa + H 2O 3) CH3COOH + Na CH3COONa + H2 4) 2CH3COOH + Na23 2CH3COONa + H2 + II. . P CH3COOH + Br2 CH2BrCOOH + HBr III. . CH3COOH + C2H5OH CO 2 O H2SO4 CH3C OC2H5 + H2O IV. . O 3CH3COOH + PCl3 3CH3C + H3PO3 Cl 12. . O CH2 O + Br2 CH C CH2 CH C OH OH Br Br . 13. O H C OH + CH3OH H2SO4 O H C O CH3 14. + H2O O , : CH3 CH2 C O H O O 1) 2CH3 CH2 C + 2Na OH 48 2CH3CH2C + H2 ONa

49. O O 2) CH3CH2C + H2O ONa O Mg + H2O CH3CH2C O 2 O + H2O + CO2 2CH3CH2C ONa O + HCl CH3CH C OH Cl O + H2O CH3 CH2C O CH 3 O 3CH3 CH2C + H3PO3 CH3CH2C + NaOH OH O 3) 2CH3CH2C + MgO OH O 4) 2CH3CH2C OH + Na2CO3 O 5) 3CH2C CH OH P + Cl2 O 6) H CH C 3 2 OH 7) 3CH CH C 3 2 + CH3OH O OH + PCl3 Cl K : O O CH3 C H C O CH2 CH3 O CH3 : 1) CH3 C O O CH3 C + H2O OH O CH3 O O + H2O H C + CH3CH2OH H C OH O CH2 CH3 O 2) CH3 C + NaOH OCH3 O CH3 C + CH3OH ONa O + CH3CH2OH HC ONa O H C + CH3OH + NaOH O CH2 CH3 15. : O H C O CH3 49

50. O O + H2O H C + CH3OH H C O CH3 O H 16. O O ) CH3 C O ) O CH3 C C OH HO O Cl O ) H C C ) H C OH Cl O OH O O ) CH3 C C CH3 ) CH3 C O CH2 CH3 O Mg O O O ) CH2 ) H C CH C O CH2 CH3 OH 17. O O H C H C OH ( ) Cl O O C2H5 () H H C C Cl OH ( ) O C H O C OH ( ) O O C C H3C C O C2H5 () O Mg H3C C O 2 50 H C HO OH ( ) O H3C C O CH3 ()

51. 18. 1,12 3,2 Cn H 2 n +1COOH + NaHCO3 Cn H 2 n +1COONa + H 2O + CO 2 ( R + 45) 22,4 x 5 22, 4 100 CO 2 + Ca (OH) 2 CaCO3 + H 2O 22,4 (CO 2 ) - 100 (CaCO3 ) x (CO 2 ) - 5 (CaCO3 ) x = 1,12 (CO 2 ) 3,7 (-) 1,12 (CO2) (R+45) (-) 22,4 (CO2) 3,722,4=1,12(R+45); 74=R+45; R=29=C2H5 : C2H5COOH 1,12 CO2. 21. . 1. : R1OR2 O : R1 C O R2 , ( ), C O ; , . 2. , , . O O + H2O + R2 OH R1 C R1 C O R2 O H 3. 2 . O O H C = 4 1 + 2 12 = 60 / O CH3 : m(H) = 4 1 = 4 ; m(C) = 2 12 = 24; m(O) = 2 16 = 32 () = 0,0667 6,67%; () = 0,5333 53,33% () = 0,4 40% O CH3 M H C 51

52. O H C OH + CH3OH H2SO4 O H C O CH3 + H2O 3 + 22 = 22 22 O + CH3OH H C H C + H2O O CH3 O H O 4. , , , . . , . 5. : , . 6. 4 : CH2 CH CH2 O O CH2 O C C15H31 CH2 O C C15H31 O O CH O C C15H31 CH O C C17H35 O O CH2 O C C17H35 CH2 O C C15H31 O O O C C17 H35 O C C17 H35 CH2 CH2 O O CH O C C15 H31 CH O C C17H35 O O O C C17 H35 O C C15 H31 CH2 CH2 O CH2 OH O C C15 H31 O CH OH+2C H31COONa+ C17 H35 COONa 15 O C C15H31+ 3 NaOH O O C C17 H35 CH2 OH , , .. 3 , , 3 , . 7. CH2 CH CH2 52 O O O C C C O O R1 R2 + 3 H2O O R3 CH2 OH R1 CH OH + R2 CH2 OH R3 O OH O C OH O C OH C

53. CH2 OH CH2= CH CH OH O +2 H2O C H CH2 OH 8. 1 15H 31COOC16H33 + 47O2 32CO2 + 32H2O n(O2)=47 n(C15H31COOC16H33)=47 1 =47 V(O2)=Vm n(O2)=22,4 / 47 =1052,8 V (O2 ) 1052,8 V.= = =5013,33 5,013 3 0,21 0,21 n(CO2)=32 n(C15H31COOC16H33)=32 1 =32 m(CO2)=M(CO2) n(CO2)=44 / 32 =1408 n(H2O)=32 n(C15H31COOC16H33)=32 1 =32 m(H2O)=M(H2O) n(H2O)=18 / 32=576 : V.=5,013 3; m(CO2)=1,408 ; m(H2O)=0,576 9. C CnH2n+1 O O + O2 3 CO 2 + H2O Ck2k+1 n+k+1=3 , H C O OH n=0; k=2 , H C O O CH2 CH3 2H H C C O O 6 CO2 +6 H2O +7 O2 O C2H5 + H2O H O C 2H5 H C O OH +Ag2 O CO 2 + H 2 O +2 Ag C O + C 2H5OH OH 53

54. 10. O C C H3 O C H2 CH C H3 C H3 1 H2SO4 O CH3 C CH3C +CH3CHCH2OH +H2O OH OCH2CHCH3 CH3 O CH3 ( m CH3 C O )=M(CH3COOH) n=60 / 1 =60 OH m(CH3 CH CH2 OH )=M(C4H10O) n=74 / 1 =74 CH3 CH3 m (C O ) =M(C H 6 O CH2 CH CH3 12O2) n=116/ 1=116 CH3 60 1 1 = =0,517 (CH3COOH) = 116 60 116 1 = 74 1 =0,638 CH CH CH ( 3 = 2 116 74 116 OH) CH3 0,517 m(CH3COOH) = = 0,862 ; 0,6 m (CH3 CH CH2 OH) = 0,638 = 1,063 0,6 CH3 : m(CH3COOH)=0,862 ; m (CH3 CH CH2 OH)=1,063 CH3 11. (C)=48,649%; ()=43,243%; ()=8,108% HyOz; x:y:z= 48,649 : 8,108 : 43,243 =4,054:8,108:2,703=3:6:2 12 1 16 3H6O2 . : H C O O 54 CH2 CH3 CH3 C O O CH3

55. O CH3C O C H +H2O OCH3 + H2O O H OH CH3 C O C H + C2H5OH + CH3OH H2SO4 H +CH3OH OH O + C2H5OH OH O C2H5 O C O CH3C C + H2O O H2SO4 CH3 C2H5 O C OH O CH3 . CH3 CH2 O C + OH C 2C H3 CH2 + H2O CH2 OH CH2 CH2 O OH O CH2 + OH CH2 OH + H C2 OH CH2 O + H CH2 O OH O CH2 CH3 +H2O C O C2H5 +2 H2O O C C2H5 C 12. , , ,.. . 1. H + HCOOK + CnH2n+1OH nH2n+1 2. y k H y + C k H 2k+1 COOH + C m H 2 m+1 OH m H 2 m +1 1- 2-, m (KOH) = 0,1 168 = 16,8 .; ( + )56 = 16,8; + = 0,3 2 +2O+ Ag 2O C nH2n+1OH +CO 2 + 2 O + 2Ag nH 2n+1 m(Ag) 21, 6 2 = = = 0, 2 ; = 0,1 = 0,2 . : M(Ag) 108 (14n + 1 + 4,5)x + (14k + 4,5 + 14m + 1)y = 22,2; 14n 0,1 + 14n 0,2 + + 14m 0,2 = 22,2 - 4,6 9,2; n + 2k + 2m = 8, 4 = 6 ; n = 2; m = 1; k = 1. 14 0,1 : 2H5 3 H3 55

56. m (HCOOC2H5) = M = 0,1 74 = 7,4 . W (HCOOC2H5) = m = 7,4 = 0,333 33,3% ; W (H3COOCH3) = 66,7% m 22,2 : W (HCOOC2H5) =33,3%; W (H3COOCH3) = 66,7%. 22. , 1. , , , 2:1. Cn(H2O)m, , .. () . 2. , . , . , . , 2 . , . , . 3. , , - . , , , . 4. , ( ), , , (, ). , , . , , (1 = 4 ), , . , , , 80% . 5. m(C12H22O11)=0,21,5=0,3 . : m(C12H22O11)=300 . 6. m=100500=50000 =5000 ; m=0,2m=0,25000=1000 m 1000 = = 1003 (). : 1003 . m= w 0,997 56

57. 23. . . 1. , , , , , Cu(OH)2, , . , , . 2. H O HO C C C H O H C OH H C OH C H H C OH + 2[Ag(NH3)2]OH H C OH +2Ag + 4NH3 +H2O H C OH H C OH H C OH H C OH H H H O HO C O C H C OH H C H H OH H t C C H H C OH + Cu2O + 2 H2O H C OH + 2Cu(OH) H C OH H C OH H C OH H C OH 2 H H H O O H C C O C H C OH H C O HO C H H C O H C OH H C O H C OH H C O C H C OH H C O C H +5CH3COOH CH3 O C CH3 O C CH3 +5H2O O O CH3 CH3 H 57

58. 3. H OH O C H C H H C OH HO C H Ni H C OH H C OH HO C H H C OH + H2 H C OH H C OH H C OH H C OH H H . 4. , , . 5. H H H H C C C C C OH OH OH OH O H CH2OH , , .. 5 , . 6. , .. , . 7. O H C H C OH HO C H H C OH H C OH H C OH H 58 2H3CH2OH 2CO2

59. H O C HO H C OH HO C H H C OH H C OH H C O OH C 2H C OH CH3 H 8. , .. . , , . 9. 144 x C6H12O6 2 CH3CHCOOH OH 180 2*90 180 (C6H12O6) 290 (-) 144 (C6H12O6) x (-) x=144 ; = 120 = 0,833 83,3%. : 83,3%. 144 10. x 3 200 .. 6CO 2 + 6H 2O C6 H12O6 + 644 3 6O 2 622,4103 3 3 644 (CO2) - 622,410 (O2) 200 . (CO2) x 3 (O2) x= 14 3 200 109 22,4 103 = 1,02 1014 3 . : 1,0210 44 11. x 20,88 180 232 C6H12O6 + Ag2O C6H12O7 + 2Ag ; 180 20,88 x= = 16,2 232 C6H12O6 + Ag2O C6H12O7 + 2Ag n(C6H12O6)=1,5 ; m(C6H12O6)=1,5180=270 : ) 16,2 ; ) 270 . 59

60. 24. . 1. 120 + nH O x 2 (C6H12O5 )n nC6H12O6 162 180 m((C6H12O6)n)=2000,6=120 ; 162 - 180 x = 120 180 = 21600 = 133,3 ; 120 - x 162 162 = 72 = 0,54 54%. : 54%. 133,3 2. x y 8 162 363 297 (C6H10O5 )n +3nHNO3 (C6H 7O 2 (NO 2 )3 )n 162 ((C6H10O5 )n ) 297 () x ((C6H10O5 )n ) - 8 () m 4,36 m. = = = 4,96 0,88 x = 4,36 3 63 (HNO3 ) - 297 () = 5,09 x (HNO3 ) - 8 () m. = m = 5,09 = 5,79 ; : m(HNO3)=5,79 ; m()=4,96 . 0,88 3. x + nH O 144 2 (C6 H10O5 )n nC6 H12O6 2nC2 H 5OH + 2nCO 2 246 162 m(C2H5OH)=0,96150=144 162 () 92 (C2H5OH) x () 144 (C2H5OH) x=253,56 . : m=253,56 . 4. 1000 + nH O x 2 (C6 H10O5 )n nC6 H12O6 2nC2 H 5OH + 2nCO 2 246 162 m()=0,25=1 =1000 162 - 92 x = 567,9 1000 - x m=4500,8=360 ; m(C2H5OH)=0,95360=342 ; = 5. n + H 2O n 2 ) (C6H10O5 )n C12H22O11 2 60 342 = 0,60 567,9

61. C12H22O11+H2OC6H12O6+C6H12O6; C6H12O6 2C2H5OH+2CO2 CH3COOH+C2H5OHCH3COOC2H5+H2O CH3COOC2H5+NaOHCH3COONa+C2H5OH 2O ) (6H10O5)n + nH nC6H12O6; C6H12O6 2C2H5OH+2CO2 Zn /A l2 O 3 CH2 CH CH CH2 + 2H2O + H2 2C2H5OH t n CH2 CH2 CH CH ( CH2 CH CH CH2)n ) 6nCO2+5nH2O(C6H10O5)n+6nO2 2O (C6H10O5)n + nH nC6H12O6; C2H5OH + CuO CH3 C t CH3C O + Ag 2O H C6H12O62C2H5OH+2CO2 O + Cu + H2O H t CH3COOH + 2Ag (C6H10O5)n+3nCH3COOH[C6H7O2(OCOCH3)3]n+3nH2O 61

62. 6. 25. 1 : CH3-NH2 ; CH3-CH2-NH2 CH3-CH2-CH2-NH2 : CH3-NH-CH3 ; CH3-NH-CH2-CH3 CH3-CH2-NH-CH2-CH3 : N CH3 CH3 CH3 CH3 N CH2 CH3 CH3 CH3 CH2 N CH2 CH3 CH3 2. CH2 CH2 CH3 NH : N H2 CH2 CH2 CH2 N H2 CH2 CH2 CH CH2 CH3 CH3 CH3 3- CH2 CH3 N H2 CH2 N H2 CH CH CH2 CH3 CH2 CH2 CH3 2- CH3 2- CH3 CH CH CH3 N H2 CH3 2--3- CH3 CH3 N H2 CH2 C CH3 62 CH3 1--2,2-

63. CH3 N H2 C CH3 2--2- CH2 CH3 CH3 CH2 CH3 CH2 CH CH2 CH2 NH NH CH3 CH3 CH3 CH3 CH CH3 CH2 CH3 CH CH3 CH3 N CH2 NH NH CH2 CH3 - CH3 CH3 CH2 CH3 CH3 N CH2 CH3 CH3 CH2 CH3 CH3 N CH CH3 CH3 3. , . 4. 11,2 H2SO4+ 2CH - NH 2 (CH3NH3)2SO4 3 V(CH3NH2)=Vm n=22,4/ 2 =44,8 m(H2SO4)=M(H2SO4) n=98 / 1 =98 11,2 98 44,8 H 2SO4 + 2CH3- NH 2 (CH3NH3)2SO4 11,2 ; 98 11,2 = 24,5 (H2SO4) = = 98 44,8 44,8 63

64. m-= m(H 2SO 4 ) 24,5 = 125 = (H 2SO 4 ) 0,196 : m- = 125 . 5. CH2=CH2 CH3-CH2-NH-CH2-CH3 1) CH2=CH2+HBr CH3-CH2-Br 2) CH2-CH2-Br+NH3 [CH3-CH2-NH3]Br [CH3CH2-NH3]Br+NaOH CH3CH2NH2+NaBr+H2O 3) CH3CH2NH2+CH3-CH2-Br [(CH3CH2)2NH2]Br [(CH3CH2)2NH2]Br+NaOH CH3-CH2-NH-CH2-CH3+NaBr+H2O 6. H N H CH3 H N CH3 CH3 +I , . , , . NH2 7. Br NH2 NH2 +3 Br2 +3HBr Br Br , , , . 8. x 51,8 NH2 + HCl 93 93 - 129 x - 51,8 64 [ NH3 129 x = 37,34 ] Cl

65. 19,9 x OH OH Br + 3Br2 Br + 3HBr Br 92 92 - 331 x - 19,9 331 x = 5,53 ; m(C6H6)=100-5,53-37,34=57,13 (); (6H5NH2)= 37,34 100% = 37,34% ; 100 (6H5OH)=5,53%; (6H6)=57,13% 9. x z CH3 NH 2 + HBr 3NH3Br . 3NH2 (7-) 2. (7-) 2 (5-) Br. M = ( 7 ) 44 + ( 5 ) 81 = 1,942 29 ; = 3 . 7 +5 : W(CH3NH2)= 3 100% = 42,9% ; 7 W(CO2)=100% - 42,9%=57,1%. : W(CH3NH2)=42,9%; W(CO2)=57,1% 10. CH3NH2+CH3BrCH3NHCH3+HBr (CH3)2NH+CH3Br(CH3)3N+HBr 26. 1. O O 1. 2NH2 CH2 CH2 C + H2SO4 OH ( NH3 CH2 CH2 C CH2 CH2 C O + H2O + NaOH NH2 CH2 CH2 C ONa OH 3. NH2 CH2 CH2 C OH O 2. NH2 )2 SO4 O +CH3OH OH H+ O NH2 CH2 CH2 C +H2O O CH3 65

66. 2. : , . O CH C NH2 OH R 3. , , , - . - (-). 4. , , , . 5. , : O CH3 CH2 CH3 CH3 CH C OH NH2 1. CH3 CH2 Ni CH = CH 2 H2O2 CH2Br CH3 + HBr t 2. CH2 = CH 3. CH2Br CH3 CH3 + KOH CH2 CH3 + H2 CH2 CH3 CH3 CH2OH + KBr CH2 O 4. CH3 CH2 2OH + CuO O 5. CH3CH2 6. CH3CH2 66 C CH3 CH2 C t CH3CH2 + 2 Cu(OH)2 H O P C + Cl2 CH3 CH OH Cl H + Cu + H2O O + Cu2O +2 H2O OH O C + HCl OH C

67. O O 7. CH3 CH C + 2NH3 OH Cl CH3 CH NH2 C + NH4Cl OH 6. R CH COOH NH2 14 (N) - 15,73% 74 ( - ) - x% x = 83,1% 100% : , . CH3 CH COOH NH2 : 14 (N) - 15,73% x = 100% : CH3 CH COOH 89 (N) - x% NH2 7. 3 + l ; 2NCH2COOH + HCl ClH3NCH2COOH; 22NCH2COOH + CaO (H2NCH2COO)2Ca + H2O; (l)= 5,38 = 0, 24 ; 22, 4 ()= 10,08/56 = 0,18 , 2NCH2COOH, . . 27. 1. , , . , , , . , , , ( ) . 2. . , 500 /. 67

68. , , , 10000 /. , , 10000-30000 /. , , 30000 /. 3. , : , . : 1. . 2. , , , , , , . 3. (). 4. : ) - . ) (II) - . 5. . : ) (); ) (); ) (); ) ( ); ) (); ) (); ) () 6. , . 7. , ( ), , , -, . , , , . , , , , . 68

69. , , : 1) ; 2) ; 3) , ..; 4) . 8. , . . 9. ( CH NH O )n+n H2O CO n NH2 CH R R 10. C2H6 1 C2H5OH 2 O C CH3 3 O CH3 C H 5 O CH2 NH2 1. C2H6 + Cl2 C C 6 OH CH3 ( OH NH CH2 CO CH2 4 OH CH2Cl C O 5 OH )n Cl +HCl CH3CH2Cl +NaOH CH3CH2OH +NaCl O t 2. C2H5OH +CuO +Cu + H2O CH3 C H O O +2Ag+4 NH3 + H2O CH3 C [ Ag(NH3)2]OH +2 3. CH3 C OH H O C 4. CH3 O + Cl2 OH CH2 Cl C + HCl OH O + 2 NH3 + NH4Cl NH2 CH2 C OH OH O C NH CH2 CO ) + n H2O n OH O 5. Cl CH2 6. n NH2 C CH2 ( 69

70. 28. 1. ) - : , , , ; : ) - - - ) 99% , ) - : , , , , , , , , , , , . , 2. ---------; --------- 3. : , ; : , ; : , . , . 4. , , . 5. , , ( ). 70

71. 6. : 1) , ; 2) , ; 3) , . 29. 1. , , , .. , , . 2. . . . 3. : 1) (1, 2, 6, 12, , ); 2) (, , D, ). 4. ) , , . , , . , , , . ) , , , . , , , . ) , , . . ) D , , 71

72. , . . . 5. , , .. , .. . . 6. . 7. , , , . : , , , . 30. 1. , . . 2. ( ), ( 1015 ). 3. , . 4. t=36oC 5. pH=6,8; pH=1,7. 6. 6 : ) ; ) ; ) ; ) ; ) ; ) , , . 72

73. 7. : , , , , , . 8. x 78 2C6 H12O6 + 3O 2 2C6 H8O7 + 4H 2O m(C6H12O6)=0,15520=78 () 78 (C6H12O6) x (C6H8O7) 2180 (C6H12O6) - 2192 (C6H8O7) x=83,2 (); m=m=0,6283,2=51,58 () : 51,58 . 9. 230 x C12 H 22O11 + 3O2 2C6 H8O7 + 3H 2O m(C12H22O11)=m=0,80,45640=230,4 342 () - 2192 (-) 230,4 () x (-) x=258,7 258,7 100% 75% = 194 . : m=194 . 10. 6126 + g2O C6H12O7 + 2Ag : 0,27 (6126) =1/2 (Ag) = = 0,00125 ; 108 V () = 5 + 5 = 10 = 0,01 ; V 0,00125 (6126) = = =0,0125/ ; 0,01 W1 = c / t = 0.125/30 = 4,17 10-3 / : V () =(4680 / 1,04) +500 (). 500/50 = 10 , 5 , . W2 = W1/5 = 8,33 10-4 / 122211 + 2= 6126 + 6126 ; ( ) = . ( 4680 0,171 = 1,17 342 (6126) = / V = 1,17 / 5 = 0,234 /; 0,234 =281. : t = 281 . t = c / W2 = 8,33 10-4 6 12 6 122211) = 0,5 73

74. 31. 1. . , , .. . 2. , (), , . 2O (C6H10O5)n + nH nC6H12O6 . 3. , , . , , . . 4. , . 5. , . . , . (C6H10O5)n+nH2O nC6H12O6; nC6H12O6 (C6H10O5)n+nH2O 7. : , . 74

75. 8. . , .. () , () . 9. I , ( OH ), C20H28O2. C II ( O C , , - C18H25O2. III ( C OH), , - C20H28O2. 10. , - , FeCl3 , , . 11. . 32. 1. , , ; , ; , . , , , - . 2. . , , . , , 3. . . . , . 4. CH2 CH CH2 ONO2 ONO2 ONO2 + 3 H2O CH2 CH CH2 OH OH + 3 HNO3 OH 75

76. CH2 CH CH2 + 3 HNO3 CH2 CH CH2 + 3 H2O ONO2 ONO2 ONO2 OH OH OH . 5. OH + NaOH COOH OH + H2O COONa OH + 2 NaOH COOH ONa + 2 H2O COONa 6. h CHCl3+Cl2 CCl4+HCl h Cl2 2Cl; Cl+CHCl3CCl3+HCl; CCl3+Cl2CCl4+Cl 7. , . , . . , . , , . , , . 8. OH + H2O COOC6H5 NaOH OH + COOH OH , , .. . 9. , . , . ( ), . 76

77. 10. : ( ) ( ). 11. , . : , . 12. : ( ), ( , , ). 13. , . , ( , , , , , ), , , . 14. , , , . . 15. , , . , . 77

78. 1. 1. : , . 44 . - CuO. , CuSO4 . , , a(OH)2. . , (II). , , (II), , . 12 CO2 +11 H2O +24Cu C12H22O 11 +24 CuO a(OH)2 + CO 2 aCO 3 + H2 O +5 H2O CuSO 4 . 5 H2O CuSO 4 : , .. , CuO . 2. : , , (II). . - , .. . 5CuO + 2CHCl3 = 3CuCl2 + 2CO 2 + H 2 O + 2Cu 2. 1. : . , . , . , 78

79. , .. . , . . Na2CO3 + CH4 CH3COONa + NaOH CH4 +2 O 2 CO 2 +2 H2O 2. : 2 , 1 , (III) . . . , , . , , , . 2 CO 2 +2 H2O CH2 = CH2 +3 O 2 CH2Br CH2Br CH2 = CH2 + Br2 2 MnO2 +3 CH2 CH2 +2KOH 3 CH2 = CH2 + 2 KMnO4 + 4 H2O OH : : C2H5 OH H 2 SO4 . : CH3 CH2Cl +KOH : CH2 CH2 +Zn Cl OH CH2 = CH2 + H2O CH2 = CH2 +KCl + H2O CH2 = CH2 + ZnCl2 Cl . 3. : 5-6 . 2 , 2 . , , , -, 79

80. , , . , , , , , , , , , . 3. 1. : 2 . 3 . , , , .. (0,8 /). . , , . 2. : 1 10%- (II) 10%- . Cu(OH)2. , . - , . Cu(OH)2 + Na2SO4 CuSO4 +2NaOH H CH2 2CH CH2 OH OH + Cu(OH)2 OH CH 2 CH CH2 O O Cu O OH O H H CH2 CH +2 H2O CH2 Cu(OH)2, .. . 3. : 2 5%- , 1 20% 0,5 , 80

81. . . . O K 2Cr2O 7 +3 C2H5OH +4 H2SO 4 Cr2(SO 4)3 + K 2SO 4 +3 CH3 C +7 H2O H , .. . 4. 1. : 1 . . . , .. . O O +2 Ag +4 NH3 + H2O H C +2 [ Ag(NH3)2 ]OH H C OH H 2. : 30 . . , . O O C C 2 + O2 2 H OH 3. - . . . . . . . O t CH3 C CH3 + Na2CO 3 2 CH3 C O Na O Na2CO3 + 2HCl 2NaCl + H2O + CO2 81

82. 5. 1. : 2 3 , . 2 - , , . . . . . . O O C C + O H +NaOH O Na H2O . 2. : 1 . . . O O Zn + H2 Zn + 2CH3 C CH3 C 2 OH O , , , . , , , . ( ) 3. : 2 , 2 - . . . , . O H 2SO 4 O CH3C + CH3CHCH2CH2OH CH3C OH CH3 O(CH2)2CHCH3+H2O CH3 , , . 82

83. 6. 1. : . . . H HO O O C C H C OH C H H C OH + 2Ag + 4 NH3 + H2O OH H C OH OH H C OH H C OH H C H H C OH H C H C +2 [Ag(NH3)2]OH H H . 2. (II) : ) - , 2 1 . (II), - . , , . CuSO4 +2NaOH Cu(OH)2 + Na2SO 4 H O H C C H C OH H C H 2 H H H C C C H O H H C OH C H OH + Cu(OH)2 H C O OH H C O H C OH OH H H O C H Cu H O C H +2H O 2 O C H HO C H HO C H CH 2OH 83

84. ) , . , . - . H O HO C O C H C H C OH H OH C HO H HO t H HO H C C H C O H C O H C OH H Cu HO C H H O C H +HO 2 O C H HO C H HO C H HO C H HO H C H +CuOH H C O H 2CuOH t Cu2O +H2O , O . C H - CuOH Cu2O, . 3. : ) . , , .. , . ) . . ( ). 2 . , . 84

85. H O CH2OH O H CH2OH C H O H H H 2 SO4 . H H H H H C + H2O OH O OH t CH2OH H OH H C H OH OH H H C OH C =O H C H H C OH + H C OH H C OH H C OH H C OH H C OH H . Na2SO4 +2 H2O H2SO4 +2NaOH H 4. : 20 , . . . . 7. . . 1. : - , . . . . . + NH2 +HCl + NH3 Cl NH3 Cl NH2 +NaOH +NaCl + H2O 85

86. 2. : - . . NH2 NH2 Br Br +3HBr +3 Br2 Br 3. : 2 (II). . . 2NH2 CH2 C O OH +CuO ( NH 2 CH2 C O O ) Cu + H O 2 2 4. : . . . , .. . 5. : CuSO4 . . (CH3COO)2Pb . . 6. ) . . . . . . ) . . - . 86

87. 8. I. . . . II. . . . III. . . . IV. , . . . V. . : 2 + 2[Ag(NH3)2]OH HCOOH + 2Ag + 4NH3 + H2O, . VI. . , . HO O H O C C H C C H H C OH H C H C H OH C H C OH H H C OH + 2Ag + 4NH3 + H2O OH H C OH OH H C OH +2[Ag( H3)2]OH N H H . VII. : 23 + Na2CO3 2CH3COONa + CO2 + H2O; 25 + Na2CO3. 87

88. VIII. . . OH OH Br Br +3HBr + 3 Br2 Br . IX. . . . 9. . 1. 1 1%- FeCl3. - , . 2. 2 , 10 . . 10-15 . , . , , , . 3. D 1 1 . - , D. 10. . 1. . 1. , 2-4 . , 10 . 2. 5 1 . 30 88

89. , . , 30 , . , . 3. 5 1 2 . (35-40 C). 30 1 , . , . , 35-40 oC ( ). 2. ( ) 1. ( ) 0,5%- . 1. 2 5 , 15 0,5%- . , . , . 3. , . 4. , (35-40 oC). , , , , (.. , ). 5. , ( ). 3. 1. 5 2 . 2. . . , . 3. . . 89

90. 4. . , .. , , ( ). 5. . , .. . 2H2O2 2H2O+O2 11. . 1. , O OH COOH O C CH3 COOH OH COOC6H5 1. . 0,1 . , . , . 2. 0,1 . , . . 3. 0,1 NaOH, . , .. , . OH + 2NaOH COOH ONa + COONa 2H2O O O C CH3 + 3NaOH COOH OH + 3NaOH COOC6 H5 90 ONa + CH3COONa + 2H2O COONa ONa + COONa ONa + 2H2 O

91. 4. 0,1 , , , FeCl3. , .. , FeCl3 2. , n-. OH NH C CH3 O OC2H5 NH C CH3 O 1. . 0,1 . . 2. 0,1 . . , . 3. 0,1 FeCl3. - , .. OH ) 91