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/ /, . . C2H2 -; H:C C:H -; H:C: : :C:H . -. , . 3 - C-H; C-C; C-H. C =>sp-. 2p C - . 2 . C-C 0,120 . 3- - -. . -: I. . , , 3- . 1. (. H2) C2H2+H2>C2H4; C2H4+H2>C2H6 HCCH+H-H>H2C=CH2; H2CCH2+H-H>H3C-CH3 2.: C2H2+2Cl2>C2H2Cl4 3. ( ) C3H4+2HBr>C3H6Br2; HC=C-CH3HBr>H2C=C-CH3; 4 2--1Br 4.. (. ) O C2H2+H2O>CH3-C H II.. 1. C2H2+3O2>2CO2+H2O+Q 2. -. ). - KMnO4 CHHC+4O>HOOC-HOOC ). III.. ( -) - - Ag CHCH+Ag2O>CAgCAg+H2O IV.. . C2H2 3C2H2>C6H6 : 1).2CH4>C2H2+2H2 2). CaC2+2H2O>C2H2+Ca(OH)2 - =O H . Ÿ ࠠ (H-C=O) H R-; - . . . : - R-CH2-O-H+O>R-C=O+H2O H - : CH4+O2>H-C=O+H2O 8 H - , . 2CH3OH+O2>2H-C=O+H2O (- ) H-CC-H+H2O>CH3-C=O H - . -, -. : : R-C=O+Ag2O>R-C=O+2Ag H OH , . . : R-C=O+2CH(OH)2>R-C=O+2CuOH+H2O H OH - -, . . H-C=O+HH>H3C-OH H : , . , . CH3-CH2-C=O+Br2>CH3-CH-C=O+HBr H Br H - CH2OC+C6H5OH>. a - 2CH2-CH2+O2>2[CH2=CH-OH]>2CH3-C=O H : /-. / 3 H H C2H4-; C=C - - H H H:C::C:H - - / H H 1. CnH2n ࠠ C=C - () H H H H 2. CnH2n-2 /⠠ C=C-C=C - () H H H H 3. CnH2n-2 H-C=C-H () , -. 3 - (C-C; C-H; C-H), sp2 , 1200, . 0,134 . 4p-. , . . -, .. . 1p- (p- -.). 2- . , .. p-. / / - CnH2n 2- , / . . CnH2n -. -. C2H4 CH2=CH2 , C2H6 CH2=CH-CH3 , C4H8 CH2=CH-CH2-CH3 , C5H10 CH2=CH-CH2-CH2-CH3 , C6H12 CH2=CH-CH2-CH2-CH2-CH3 , . -: 2-4 , ; C5-C18 ; C19- - -, / H2O . - /: I. : C2H4+3O2>2CO2+2H2O+Q II. . ). : C2H4+H2>C2H6; CH2=CH2+H-H>CH3-CH3 ). : C3H6+Br2>C3H6Br2; CH2=CH-CH3+Br-Br>CH2-CH-CH3 Br Br 1,2- ).: C2H4+H2O>C2H2OH; CH2=CH2+HOH>CH3-CH2-OH ).. ( . ). H2 . C 2- , . C. C3H6+HCl>C3H7Cl; CH2=CH-CH3+HCl>CH3-CH-CH3 Cl 2- III. . , . nCH3=CH2>(-CH2-CH2-)n, n- , (-CH2-CH2-) IV. . - / ). . - KMnO4: CH2=CH2+O+H2O>CH2-CH2- OH OH ). . Br2: CH2=CH2+Br2>CH2-CH2 1,2- Br Br . / . /, . . CH -ࠠ CH CH . - C6H6- CH CH . - ࠠ CH I. . : 1).2C6H6+15O2>12CO2+6H2O+Q 2). ., -, . . ( ). O 5 C6H5-CH3+3O>C6H5-C +H2O OH II.. . 3). C6H6+Br2>C6H5Br+HBr 4). C6H6+HONO2>C6H5NO2+H2O III. . ; 5). C6H6+3H2>C6H12 6). C6H6+3Cl2>C6H6Cl6 . . . / -. . , . /, . . , .. - . . . : . , . . 1. 2. 3. 4. / 5. . , . 6. 7. . . - / . , . /. R-OH R-- 65 . - . , . : . . : C6H6>C6H5Cl>C6H5OH 7 : . - , t=40,90. , t=700C . . : . -: 2C6H6OH+2Na>2C6H5ONa+H2 : . .:C6H5OH+NaOH C6H5ONa+H2O , .. . (3). . . : 1. 7. 2. . 8. * 3. 9. * 4. 10. *. 5. 11. 6. . 12. - (- * ) - (=O,-H) . Ÿ ࠠ (H-C(=O,H) R-; - . . . : - R-CH2-O-H+O>R-C=O+H2O H - : 8 CH4+O2>H-C=O+H2O H - , . 2CH3OH+O2>2H-C=O+H2O (- ) H-CC-H+H2O>CH3-C=O H - . -, -. : : R-C=O+Ag2O>R-C=O+2Ag H OH , . . : R-C=O+2CH(OH)2>R-C=O+2CuOH+H2O H OH - -, . . H-C=O+HH>H3C-OH H : , . , . CH3-CH2-C=O+Br2>CH3-CH-C=O+HBr H Br H - CH2OC+C6H5OH>. a - 2CH2-CH2+O2>2[CH2=CH-OH]>2CH3-C=O H : /-. . . . . - , . / H2. O: O R : C R-C =R-COO-+H+ . . - :O : H OH , . , . - H2 . O (- -). R-C O-H - HCOOH- -, . , . 2- - ; - . 3- . 4- : I. : 5- 2R-C=O ONa+H2SO4>Na2SO4+2R-C(=O,-OH); 2CH3-(CH2)16- 6- -C(=O,-Na)+H2SO4>Na2S04+2CH3-(CH2)16-C(=O,-OH) 9 18- II. - /: 1. 2CH3+3O2>4CH3-C(=O,-OH)+2H2O 2. 2C4H10+5O2>4CH3-C(=O,-OH)+2H2O III. : R-CH3O+[O2]>R-C(=O,-OH)+H2O IV. : 2R-C(=O,-H)+O2>2R-C(=O,-OH) V. . : 1. R-OH+CO>R-C(=O,-OH) 2. CO+NaOH>HCOONa; HCOONa+H2SO4>HCOOH+NaHSO4 . -: . . , . H2O. - - . - CH3-(CH2)7-COOH . - , . H2O. . - 1. - ( H2) 2C(=O,-OH)=H+R-CO(=O) 2. . 2R-C(=O,-OH)+Mg>(R-COO)2Mg+H2 R-COO-+2H++Mg0>2CH3COO-+Mg2++H20; 2H++Mg0>Mg2++H20 3. . 2R-COOH-MgO>(RCOO)2Mg+H2O 4. . - 2R-COOH+CaCO3>(R-COO)2Ca+H2CO3(-H2O,-CO3) 5. CH3-COOH CH3-C(=O,-O) CH3-COOH> CH3-C(=O,O) +H2O - 6. . CH3-COOH+HO-C2H11>H2SO4CH3-C(=O,-O-C3H4)+H2O . 7. CH3-COOH+Cl2>Cl-CH2-C(=O,-OH)+HCl - . - -. . . . . -. (. . ). HCOOH+Ag2O>H2OHOC(=O,-OH)+2Ag HOCOOH=H2O+CO2. . H2SO4, H2O . (II): HC(=O,-OH)>H2SO4, t H2O+CO2 H O H>C>C H O-H . ). HCOOH; 1. . - - -; 2. ; 3. 1,25% - ). CH3COOH; 1. ; 2. ; 3. ; 4. ; 5. . ; 6. . 13 ( ) :NH2 C : NH2 HC CH 1. C6H5-NH2 2. HC CH 3. CH . NH2 . , / , , - . - , -. . H2, . Fe+2HCl>FeCl2+2H C6H5-NO2+6H>C6H5-NH2+2H2O . . : R-CH-COOH; R-H,CH3; HO-CH2; . NH2 - a . : . (C, H, O, N) : (Fe, S, P, .) : , , , . ( 19) ()- . O H O H O H2N-CH2-C +N-CH-C + N-CH-C> 16 OH H CH3 OH H CH2 H 5H O H O H O >H2N-CH2-C + N-CH3 +C-N-CH2-C+H2O OH H CH2 H 5H : . ( ). - . . - . ) - +HNO3> . ) - +- NaOH+- CHSO4> . , , , , . - - . : 1. 2. 3. : 1. . - 2. : /, . - . - : 1. - 2. 3. -. 4. 5. /: 1. : , , . /, . : ( ..) :1. 20 2. > 3. 堠 2.. / (, , ) , . - , , , , . (40-2000-),(450-2500-) (180-3100-)(190-3500-)... 3.- 12., : (C6H10O5)n- 1. . 2. : -20%,-80%. a- . a- . : , , , , . : 1. - I2. (C6H10O5)n+I2-> . 2. - H2O ( ) (C6H10O5)n+ nH2O-H2SO4>nC6H12O6 1811. . : (C6H10O5)n->(C6H10O5)m->xC12H22O11->nC6H12O6-> . 3.- . 12 6CO2+6H2O->6H12O6+ 6O2 n6H12O6->(C6H10O5)n +nH2O : 1. , -, . : (C6H10O5)n- . . b- , . : - , , , , , , , . (2) , . . -. 1. : (C6H10O5)n+ nH2O-H2SO4>nC6H12O6 2..: (6H7O2)-3OH +2nHONO2-H2SO4>(C6H7O2 ) O-NO2 O-NO2 + 2nH2O n OH n 3. 4. , 4 5. , . , , , -, . : 1. - , , , -. 15 15. . : nCH2=CH2-t,p>(- CH2-CH2-)n- - - . . - (). - . : (- CH2-CH2-)n . t, t (IV), t , . >Mr . 18. -. 18 - . . s-s-;s-p- . . 1. . : )CH3-CH2-CH2-CH2-CH3 ) CH3-CH-CH2-CH3 2- 17 CH3 ) CH3 CH3--CH3 2,2- CH3 2. 3 C4H6- )CH3-CH2-=H 1- ) CH3-C=-CH3 2- 3. . 37O2N NH2- CH2-CH2-C(=O,-OH) 3- CH2-CH-(=,-)2- 4., . 1733O- - ) H H C C CH3(H2)7 CH3(H2)7-COOH ) CH3-(H2)7 ͠ =Ѡ - ͠ (H2)7-Π - - , . . - . . . .: C17H35COOH C15H31COOH . . . . . . C17H33COOH-, C17H31COOH- C17H29COOH. CH2-O-C(=O,-R1) CH-O-C(=O,-R2) CH2-O-C(=O,-R3) , , . . . . -: , ( ). -, . . ( ). . -. 1. R-C(=O,-O-R1)+H2O>R-C(=O,-OH+R1OH) 2.. C17H35-C(=O,-O-CH2) C17H35-C(=O,-O-Na) CH2-OH C17H33-C(=O,-O-CH) +3NaOH>t C17H33-C(=O,-O-Na) + CH-OH C17H31-C(=O,-O-CH2) C17H31-C(=O,-O-Na) CH2-OH 10 3.. . . C17H33(=O,-O-CH2) C17H35-C(=O,-O-CH2) C17H31(=O,-O-CH) +6H>t, p, Ni C17H35-C(=O,-O-CH) C17H29(=O,-O-CH2) C17H35-C(=O,-O-CH2) : - : )., ).; . : 2CH3(CH2)34CH3+502>2H2O+4CH3(CH2)16-C(=O,-OH) - C17H35COOH+NaOH>C17H35COONaOH+H2O ). C17H35COOH+KOH>t C17H35COOK+H2O 2C17H35COOH+K2CO3>t 2C17H35COOK+H2O+CO2 ). (): H2SO4. R-CH2-OH-K2-O-SO2-OH>R-CH2-O-SO2-OH-H2O R-CH2-O-SO2-OH-NaOH>R-CH2-O-SO2-ONa-H2O . . . : , , , . . -: - , , . . C6H12O6 1. - +Cu(OH)2> - => OH-=> 2.- +Cu(OH)2>t =>. C(=O,-H) => CH2-CH-CH-CH-CH-C(=O,-H) 11 OH OH OH OH OH . CH2COH CH-OH O CH-O CH C > CH CH OH CH-CH H OH CH-CH OH OH OH OH OH C-C , . 6-, 5- C. 6- , . O2. , - . 2 . :. Oh C1 2: - 1 2, b- . -(34%)> (2%)>- (64%) . -. 1. - (II) H-C-CH-CH-CH-CH-CH2 +HO >H-C-CH-CH-CH-CH-CH2 +2H2O O OH OH OH OH OH HO Cu > O OH OH OH O O Cu H-C-CH-CH-CH-CH-CH2 >H2SO4, t CH2-CH-CH-CH-CH-CH-C-H O OH OH OH OH OH O O O O O O O + COOH COOH COOH COOH COOH C C C C C C CH3 CH3 CH3 CH3 CH3 CH3 O CH3 O CH3 O CH3 O CH3 O CH3 O + -ࠠ . 2. Cu2-(CHOH)4-C(=O,-H)+2Ag2O>t CH2(-OH)-(CHOH)4-C(=O,-OH)+2Ag Cu2-(CHOH)4-C(=O,-H)+Cu(OH)2>t CH2-(CHOH)4-C(=O,-OH)+Cu2O+2H2O - 3..: CH2-(CHOH)4-C(=O,-H)+H2>t, Ni CH2-(CHOH)4-CH2 C6H12O6>t 2C2H5OH+2CO2 C6H12O6>t 2CH3-CH( OH)-COOH - .1. (. ) C6H12O6+6O2>6CO2+H2O+Q 2. 3. - 4. - 5. 1. 1 頠 4- 2. 蠠 3. ࠠ -- 4. . 1861.- 蠠 1. - , 24Br2-4-  H H -. H-C-C-H 2. ⠠ H H , () IV 38- CH3-CH2-CH3 3.- - . 4. . - - -. CH3COOH -ࠠ CH2(-Cl)COOH- - 100 . : , . - - . -, . 5. . . 6. . , - , - - . : , . H H H 14 1.H-N-CH2-C(=O,-OH)+H-N-CH2-C(=O,-OH)>H2N-CH2-C(=O)-N-CH2--C(=O,-OH)+H2O CnH2n+2 R-OH R-(OH)n 19 CnH2n, . / CnH2n+1OH 11,12 R-C(=O,-H) 13,14 4 6 R-C(=O,-OH) 8 9 CnH2n-2 -. / . / 17,18 3 27,28 R-C(=O,-O-R) R-C(=O,-O-R1) 7 CnH2n-2 - / 19,20 2 R-NH2 R NH R- N-R2 R1- R1- 25,26 15,16 CnH2n, - 1 23,24 21,22 -C-C(=O,-OH) NH2 10 5 1. +NONO2>H2SO4, t +H2O; +6H> +2H2O 2. +Cl2>FeCl3 +HCl; +NaOH>t,p +NaCl 3.2CH4+3O2>.2H-C(=O,-OH)+2H2O 4.CH4+O2>t, .H-C(=O,-H)+H2O 5.CH4+Cl2>CH3Cl+HCl; CH3Cl+KOH>tCH3OH+KCl 6.C2H2+KOH>HgSO4CH3-C(=O,-H) 7.3C2H2>t, C C6H6 8.CH3-CH2OH+CuO>t CH3-C(=O,-H)+Cu+2H2O 9.CH3-C(=O,-H)+Ag2O>t CH3-C(=O,-OH)+2Ag 10.CH3-C(=O,-O-CH3)+HOH=t, H2SO4 CH3-C(=O,-OH)+CH3OH CH3-C(=O,-OH)+Cl2>CH2-C(=O,-OH)+HCl Cl CH2-C(=O,-OH)+NH3>CH2-C(=O,-OH)+HCl Cl NH2 11.CH3-CH3>Ni, t CH2=CH2+H2 12.CH2=CH2+H2>Ni CH3-CH3 13.2CH4>t C2H2+3H2 14.C2H2+2H2>Ni, t C2H6 15.C3H8+2Cl2> C3H6Cl2+2HCl CH2 CH2 CH2 CH2 +Zn>t CH2 CH2 +ZnCl2 Cl Cl 16. CH2 +H2>Ni CH3 CH2 CH2 17.CH2=CH2>Ni, t CH=CH+H2 18.CHCH2+H2>Ni, t CH2=CH2 19.CH2=CH-CH2-CH3>t, MgO CH2=CH-CH=CH2 20.CH2=CH-CH=CH2+H2>Ni CH3-CH=CH-CH3 21.CH2=CH-CH=CH2+H2>Ni CH3-CH=CH-CH3 CH3-CH=CH-CH3+HOH>H2SO4, t CH3-CH( -OH)-CH2-CH3 22.2CH3-CH2-OH>t, Al2O3 CH2=CH-CH=CH2+2H2O+H2 23.CH3=CH-CH2+HOH>H2SO4, t CH3-CH(-OH)-CH3 24.CH3-CH( OH)-CH3>H2SO4, t CH2=CH-CH3 25. CH2 CH2 CH2 >Pt, t 3H2 CH2 CH2 CH2 26. +3H2>Ni, t 27.CH3-C(=O,-OH)+C2H5OH>t CH3-C(=O,-OC2H5) 28.CH3-C(=O,-OC2H5)+HOH>t CH3-C(=O,-OH)+C2H5OH : Cn+H2n+1OH : - , , 6 OH. () 2H6O H H H H H CC>O<H H-C-O-C-H H H ߠ H H -, . . -: 1. , -. 2. : 2CH3-CH2-OH+2Na>2CH3-CH2-Ona+H2| 렠 CH3-CH2-Ona+HOH= CH3-CH2-OH+NaOH 3. H2SO4 : CH3-OH+H-CL>H2SO4CH3CL+H2O 렠 4. t /: H3C-CH2-OH>t>140CH2SO4H2C=CH2+H2O t :( ) 5. : H H H-C-C-O-H+CuO>CH3-C-H=O+Cu+H2O : 6. 7. . . .-.1-11- P t .12-. Mr . :1. 2. -,. 3. .4. :1. , , , . : Cn+H2n+1OH : - , , 6 OH. () 2H6O H H H H H CC>O<H H-C-O-C-H H H ߠ H H -, . . -: 1. , -. 2. : 2CH3-CH2-OH+2Na>2CH3-CH2-Ona+H2| 렠 CH3-CH2-Ona+HOH= CH3-CH2-OH+NaOH 3. H2SO4 : CH3-OH+H-CL>H2SO4CH3CL+H2O 렠 4. t /: H3C-CH2-OH>t>140CH2SO4H2C=CH2+H2O t :( ) 5. : H H H-C-C-O-H+CuO>CH3-C-H=O+Cu+H2O : 6. 7. . . .-.1-11- P t .12-. Mr . :1. 2. -,. 3. .4. :1. , , , .

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