כימיה אורגנית ופולימרים

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כל חומר הקורס כימיה אורגנית ופולימרים להנדסת מכונות במכללת אורט בראודה

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<p> ' 11</p> <p> ? . , , , . . </p> <p>2</p> <p> ? . , , , . .</p> <p>3</p> <p> ( ) 02 .</p> <p>4</p> <p> DNA V 5</p> <p> TNT 6</p> <p> C-C - C-H . 4 , . , ( ). 5.2, (, , ), (). </p> <p>7</p> <p> " . , "".8</p> <p> : . , . . .9</p> <p> . . 901. . .</p> <p>01</p> <p> : 4CH : : 05.901</p> <p>11</p> <p> : 4C2H : : 0021</p> <p>21</p> <p> : 2C2H : : 0081</p> <p>31</p> <p> : 6C3H</p> <p> 21C6H</p> <p>41</p> <p> "": 8C8H</p> <p>51</p> <p> , . : , , "" .R , .</p> <p>61</p> <p> R , . , , .</p> <p>71</p> <p> . : ) - CnH2n+2 :(Alkanes ( ). ) - CnH2n :(Alkenes . ) CnH2n-2 :(Alkynes . ) CnH2n :(cycloalkanes .81</p> <p> C C</p> <p> : )(Alkenes</p> <p>C</p> <p>C</p> <p> : )(Alkynes91</p> <p> -OH : )(AlcoholsO R H</p> <p>R-OH : ( = R ))</p> <p>-O : ):(EthersO R 'R</p> <p>R-O-R</p> <p> :02</p> <p> )(X = F , Cl , Br , I -X</p> <p> : Alkyl halides R-X :</p> <p> ):(Amines , 3.NH : 2R-NH : R-NH-R :</p> <p>12</p> <p>'R N R ''R</p> <p> --CO . -. </p> <p>C</p> <p>O</p> <p> .22</p> <p> ):-CHO (Aldehydes RCHO OR C H</p> <p> ):CO- (Ketones O R C 'R</p> <p>32</p> <p> ):-COOH (Carboxylic acidsO R C OH</p> <p>O R C 'OR</p> <p> ):COO- (Esters </p> <p>42</p> <p> ):CONH- (Amides O 'R C NH R</p> <p>52</p> <p> 2</p> <p> . : ) - CnH2n+2 :(Alkanes ( ). ) - CnH2n :(Alkenes . ) CnH2n-2 :(Alkynes . ) CnH2n :(cycloalkanes .Molecular models</p> <p> Alkanes . :2+CnH2n : : ane : 4Methane - CH </p> <p> 4CH </p> <p>- </p> <p> , ) (</p> <p> ), (</p> <p> ) (</p> <p> Alkanes . :2+CnH2n : : ane 4Methane - CH 3Ethane - CH3CH </p> <p>(C1 C10 ( Methane - CH4 Ethane - CH3CH3 Propane - CH3CH2CH3 Butane - CH3CH2CH2CH3 Pentane - CH3CH2CH2CH2CH3 Hexane - CH3CH2CH2CH2CH2CH3 Heptane - CH3CH2CH2CH2CH2CH2CH3 Octane - CH3CH2CH2CH2CH2CH2CH2CH3 Nonane - CH3CH2CH2CH2CH2CH2CH2CH2CH3 Decane - CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3</p> <p> 01C4H</p> <p>3CH3CH2CH2CH</p> <p> 01? C4H</p> <p>H H3C C CH3 CH3</p> <p>H3C</p> <p>CH2</p> <p>CH2</p> <p>CH3</p> <p>Isobutane</p> <p>n-butane (normal)</p> <p>. </p> <p> : , . : 01C4HH H3C C 3CH Isobutane 3CH</p> <p>H3C</p> <p>2CH</p> <p>2CH</p> <p>3CH</p> <p>n-butane )(normal</p> <p> ()</p> <p> 4CH 6C2H 8 C3 H 01C4H 21C5H 41C6H 61C7H 22C10H 24C20H</p> <p> 1 1 1 2 3 5 9 57</p> <p> 4CH 6C2H 8 C3 H 01C4H 21C5H 41C6H 61C7H 22C10H 24C20H</p> <p> 1 1 1 2 3 5 9 57 913,663</p> <p> : 21C5H 41C6H 1. 2.</p> <p> , 2+CnH2n</p> <p>: : 5.2 : 1.2 C-C H-C . . , --..</p> <p> MW 4CH 01C4H 61C7H H2O 61 85 001 81 )bp (C 7.161- 5.0- 4.89 001 )mp (C 5.281- 5.831- 6.09- 0 )d(g/ml 664.0 106.0 486.0 00.1</p> <p> 2+CnH2n1= n 4= - n . 5= n 81= - n 81&gt;n</p> <p> 261- 004 003 002 001( ) ' </p> <p> 4CH 6C2H 01C4H 21C5H 41C6H 61C7H</p> <p>24- 5.0- 63 96</p> <p>0</p> <p>001- 002-</p> <p>0</p> <p>001</p> <p>002 </p> <p>003</p> <p>89</p> <p> : , . : . .</p> <p> 01C4H bp )(C 5.0- 7.11- mp )(C 3.831- 4.951- d )(g/ml 106.0 755.0</p> <p> , . . : . .</p> <p> 21C5H bp )(C mp )(C d )(g/ml</p> <p>1.639.72 4.9</p> <p>8.921-9.951- 8.61-</p> <p>626.0026.0 095.0</p> <p> , "" . , .</p> <p>() IUPACInternational Union of Pure and Applied Chemistry</p> <p> . . . . .</p> <p> CH3 Methyl CH3 CH2 Ethyl CH3 CH2 CH2 Propyl CH3 CH CH3 Isopropyl (1-Methylethyl) CH3 CH2 CH2 CH2 Butyl CH3 CH CH2 CH3 Isobutyl (2-Methylpropyl) CH3 CH3 CH2 CH CH3 sec-Butyl (1-Methylpropyl) CH3 C CH3 tert-Butyl (1,1-Dimethylethyl)</p> <p> IUPAC ?1 2 3</p> <p>3CH3CHCH 3CH</p> <p>1. . 3 - .</p> <p>2. / / : 3 - CH. 3. . 2 2-methylpropane : 2-</p> <p>() IUPAC , .</p> <p> IUPAC3CH3CH2CH2CH2CH(CH2CH3)CH(CH3)CH2CH</p> <p> ?1</p> <p>2 7 6 5 4 3 8</p> <p>8 : : : , . 4-ethyl-3-methyloctane</p> <p>() IUPAC . , - , - , -, ' , .</p> <p>IUPAC ? </p> <p>2,3-dimethylpentane</p> <p>CH3CH2CH2C(CH3)2CH(CH3)CH2CH33,4,4-trimethylheptane</p> <p>IUPAC 4</p> <p>12</p> <p>. </p> <p>4-tert-butyloctane 4-(1,1-dimethylethyl)octane</p> <p> 1,1,1,3,3,3-hexachloropropane 1,1,1,3,3,3-2</p> <p>3Cl3C-CH2-CCl</p> <p>BrH2C7</p> <p>1 3 5 2 1</p> <p>5-(2-bromoethyl)-2-methyloctane 5-(2-)-2-</p> <p>8 6</p> <p>4</p> <p> 3</p> <p> :. : (). . , , .</p> <p> :</p> <p> ((Naphtenes</p> <p> )(Paraffines</p> <p> )(Aromatics</p> <p> (") 4-1 11 - 5 31 - 7 61 - 01 52 - 51 07 - 02 07</p> <p>)Tb (oC - 03 021 - 03 002 - 001 052 - 051 053 - 052 005 - 053 005</p> <p> , , </p> <p> () . "" : " " . : () </p> <p> Cracking . . . : . .</p> <p> ,9000C . :2CH3)CH2)10CH3 CH3(CH2)8CH3 + CH2=CH</p> <p> , , . : .</p> <p> () - , 4500C .5500C :61CH3)CH2)12CH3 CH3(CH2)4CH=CH2 + C7H : . " " , . .</p> <p> : ( ):X-Y X + Y</p> <p> , , :X-Y -:X+ + Y</p> <p> : C-C ( C-H )</p> <p> C-C: C-C .D 3CH3CH2CH2CH</p> <p> 122 CH3CH</p> <p>D</p> <p> 23CH3CH2CH2 + CH</p> <p>3CH3CH2CH2CH</p> <p>CH3CH2CH2CH3</p> <p>D</p> <p>I CH3CH2</p> <p>II</p> <p>III</p> <p>+ CH3CH2CH2 + CH3</p> <p>: CH3CH2CH2CH2CH2CH3</p> <p>II +II I +II</p> <p>CH3CH2CH2CH2CH3CH3CH2CH3 CH3CH3</p> <p>I +III III +III</p> <p> ( H- C ): C-H . R 13R + CH3CH2CH2CH + R 2RH + CH3CH2CH2CH</p> <p> 23CH3CH2CH2CH + RH 3CH3CH2CHCH</p> <p> , . .</p> <p> ( ).2R + CH3CH2CH + RH</p> <p> ] 2[CH3CHCH</p> <p>2CH3CH=CH</p> <p> .</p> <p> () ) - (Combustion . - , ( ).: .)2C4H10 (g) + 13O2 (g) 8CO2 (g) + 10H2O (g H = -2879kJ/mol</p> <p> () , . : ().</p> <p>: - .)2CH4 (g) + 3O2 (g) 2CO (g) + 4H2O (g )CH4 (g) + O2 (g) C (s) + 2H2O (g</p> <p> 4</p> <p> () </p> <p> Substitution Reaction : A-B + C-D A-C + B-D</p> <p> , . :H C H H H Methane + Cl-Cl Light H C H H Cl Chloromethane + H-Cl</p> <p>CnH2n+2 + X2 CnH2n+1X + HXhn H3C-CH3 + Cl2 H3C-CH2Cl + HCl (1) . hn X=Cl, Br, I</p> <p>(2) .(3) , . : 4CH 2Cl hn 4CH3Cl + CH2Cl2 + CHCl3 + CCl</p> <p> : . . : () (, ) ()</p> <p> hn X2 2 X</p> <p> () ()</p> <p>CnH2n+2 + X HX + CnH2n+1 CnH2n+1 + X2 CnH2n+1X + X</p> <p> () : 1. </p> <p>+ R + R</p> <p>R</p> <p>R-R RH + R-CH=CH-R</p> <p>2. .</p> <p> R-CH2-CH-R</p> <p> : - ( ).</p> <p> , . : . ?2CH3CH2CH2CH3 Cl CH3CH2CH2CH2 Cl Light and 3CH3CHCH2CH Cl </p> <p>%06 %04</p> <p> () .</p> <p> , .2CH3CH2CH2CH3 Cl CH3CH2CH2CH2 Cl Light and 3CH3CHCH2CH Cl </p> <p>%54</p> <p>%55</p> <p> .</p> <p> 2H3C &lt; H3C-CH2-CH 01</p> <p> 3&lt; H3C-CH-CH 02</p> <p> &lt; (H3C)3C 03</p> <p> , , .</p> <p> :2Cl2 &gt; Br . 2 I ( ). 2 F ( ). , .</p> <p>2CH3CH2CH3 Cl CH3CH2CH2 Cl Light and 3CH3CHCH Cl</p> <p>%04</p> <p>%06</p> <p>: .</p> <p>3CH3CH2CH</p> <p>2Br CH3CH2CH2 Br Light and 3CH3CHCH Br</p> <p>%3 %79</p> <p> ?</p> <p>&gt;=</p> <p>1) ) : -2 () -2,4 -2,2,3 ) ? ) , ?</p> <p>2) .</p> <p>CnH2n</p> <p>cyclopropane cyclobutane</p> <p>cyclopentane cyclohexane</p> <p>cycloheptane</p> <p>cyclooctane</p> <p>06</p> <p>09</p> <p>801</p> <p> :</p> <p>901</p> <p>03</p> <p>) Strain energy (kcal mol</p> <p>3</p> <p>1-</p> <p>4</p> <p>52 02 51 01 5 0 2 4 6</p> <p>9 7 5 68 01 21</p> <p>41 21</p> <p>61</p> <p>41</p> <p>61</p> <p>81</p> <p>n</p> <p> , "" ).(cyclo , , .</p> <p>CH3</p> <p>CH3</p> <p>1,3-Dimethylcyclohexane</p> <p> : () , . : .</p> <p> 5</p> <p> - - . / : ( - 1) ( - 2)</p> <p> Alkenes CnH2n </p> <p>C</p> <p>C</p> <p> ( ) ( .) ) (Olefines .</p> <p>Alkenes C2H4 C3H6 C4H8 C5H10 C6H12 ethene (ethylene) propene (propylene) butene (butylene) pentene hexene</p> <p> , .ene , . . .</p> <p>H C H C</p> <p>H H</p> <p>CH2=CH2</p> <p>H C H C</p> <p>CH3 H</p> <p>CH3CH=CH2</p> <p>? CH2=CHCH2CH3 1-butene</p> <p>CH3CH=CHCH3</p> <p>2-butene</p> <p> : . , .: 8?C4H 01?C5H</p> <p>? 2-butene </p> <p>H</p> <p>CH3</p> <p>CH3 C H C</p> <p>CH3 H</p> <p>C C H CH3 trans-2-butenem.p. -1050C b.p. 10C</p> <p>cis-2-butenem.p. -1390C b.p. 3.70C</p> <p> . . . , .</p> <p>3-heptene :1 CH3CH2CH=CHCH2CH2CH3</p> <p>CH3CH2 C C H</p> <p>H CH2CH2CH3</p> <p>CH3CH2 C C H</p> <p>CH2CH2CH3 H</p> <p>trans-3-heptene</p> <p>cis-3-heptene</p> <p>4-ethyl-3-heptene :2 CH3CH2CH=CCH2CH2CH3 CH2CH3</p> <p>CH3CH2</p> <p>CH2CH3</p> <p>CH3CH2</p> <p>CH2CH2CH3</p> <p>CH</p> <p>CCH2CH2CH3</p> <p>CH</p> <p>CCH2CH3</p> <p>trans-4-ethyl-3-heptene</p> <p>cis-4-ethyl-3-heptene</p> <p>3-ethyl-3-hexene :3 CH3CH2CH=CCH2CH3 CH2CH3</p> <p>CH3CH2</p> <p>CH2CH3</p> <p>CH</p> <p>CCH2CH3</p> <p>.3 </p> <p> .: RCH=CHR RCH=CHR RRC=CRR</p> <p> . . . . 4 . - 5 81 . - 91 . . </p> <p> : )(additionC C + X-Y C C X Y</p> <p> , , .</p> <p> 2 Cl 2Br</p> <p>C</p> <p>C</p> <p>+ Cl-Cl</p> <p>C C Cl Cl</p> <p>CH3CH CHCH3 + Cl2 CH3CH CH CH3 Cl Cl2-butene 2,3-dichlorobutane</p> <p> - </p> <p> )(hydrogenationC C + H-H C C H H</p> <p> (). : , , . : .</p> <p> . . . , .1.</p> <p>2.</p> <p>3.</p> <p>4.</p> <p>Pt</p> <p>CH2=CHCH2CH2CH3 + H2 CH3CH2CH2CH2CH31-Pentene n-Pentane</p> <p> - . .RT . .RT</p> <p> HBr( HX )HCl</p> <p>C</p> <p>C</p> <p>+ H-Br</p> <p>C C H Br</p> <p> : </p> <p> HBr HCl</p> <p> HBr HCl : + H , . ).(carbocation ( ) .1.</p> <p>2.</p> <p> (9681) : . .</p> <p>: / .</p> <p> ?</p> <p>: / .</p> <p> .+H</p> <p>C</p> <p>C</p> <p>+</p> <p>H2O</p> <p>C C H OH</p> <p> : .</p> <p>H+</p> <p>CH2=CHCH2CH2CH3 + H2O 1-Pentene</p> <p>CH3CHCH2CH2CH3 + CH2CH2CH2CH2CH3 OH2-Pentanol</p> <p>OH1-Pentanol? </p> <p> - Alkynes : 2-CnH2n . </p> <p>C</p> <p>C</p> <p> ( ) ( .) : 1.21 1.34 : 1.54 :</p> <p>C2H2 C3H4 C4H6 C5H8 C6H10 ethyne (acetylene) propyne (methylacetylene) butyne pentyne hexyne</p> <p> , .yne , . . .</p> <p>H C</p> <p>C</p> <p>H</p> <p>ethyne (acetylene)propyne (methylacetylene) 1-butyne (ethylacetylene)</p> <p>H CH CCH3 C</p> <p>CCC</p> <p>CH3CH2CH3CH3</p> <p>2-butyne (dimethylacetylene)</p> <p>. </p> <p> : )(additionY C C + X-Y X C C</p> <p> .trans , .</p> <p>: H H C C H + Br2 Br C C H Br</p> <p>ethyne</p> <p>trans-1,2-dibromoethene</p> <p>H C Br C</p> <p>Br + Br2 H H</p> <p>Br Br C C H Br Br 1,1,2,2-tetrabromoethane</p> <p> 6</p> <p> Alcohols : R-OH ,HOH .R</p> <p>O R H</p> <p> : - HO ).(hydroxyl</p> <p> methanol CH3OH</p> <p>ethanol CH3CH2OH</p> <p> 3 , .1- CH3CH2CH2OH 1-propanol3CH3CHCH OH</p> <p>2- 2-propanol</p> <p> OH . OH . OH .</p> <p> "" ) (ol . .</p> <p> - ( ).:</p> <p>HOCH2CH2OH</p> <p> ( :(antifreeze</p> <p> .b.p )(0C 461- 56 6.88- 5.87 .m.p )(0C 5.381- 89- 381- 711- </p> <p> , , .</p> <p> ( 3= )n . , , .</p> <p> g/100g (200C) 7.9 2.7 0.59</p> <p>b.p.(0C)65 78.5 97 117.7 137.9 155.8</p> <p>CH3OH CH3CH2OH</p> <p>methanol ethanol</p> <p>CH3(CH2)2OH 1-propanol CH3(CH2)3OH CH3(CH2)4OH CH3(CH2)5OH 1-butanol 1-pentanol 1-hexanol</p> <p>: . , , . .</p> <p> .</p> <p> CH3OH . : . , . </p> <p> - .CO + 2H2 CH3OH : : 300-4000C : 200 atm : 3Cr2O ZnO</p> <p> CH3CH2OH . . 2C6H12O6 2 CH3CH2OH + 2 CO . %51 . %59 ( ). </p> <p> , CH2=CH2 + H2O CH3CH2OH : : 3000C : 68 atm : 4H3PO</p> <p> (). . . </p> <p> () , , . .</p> <p> , : CH3CH2CH2-Cl + NaOH CH3CH2CH2-OH + NaCl</p> <p> () .2CH3CH2OH CH2=CH+H+</p> <p>H2 O</p> <p> . CH3CH2OH + HCl CH3CH2Cl + H2O . .</p> <p> 7</p> <p> Ethers : R-O-R ,HOH .R .</p> <p>O R 'R .</p> <p> 3CH3-O-CH3CH3CH2-O-CH2CH 3CH3-O-CH2CH</p> <p> .</p> <p> .b.p )(0C 42- 56 6.43 5.87 .m.p )(0C 041- 89- 611- 711- M )(g/mol 64 23 47 64 </p> <p> , , . : . , , .</p> <p> :2 CH3CH2OH CH3CH2-O-CH2CH3 + H2O 4 H2SO, .1400C</p> <p> :</p> <p>R C H O</p> <p> :</p> <p>C</p> <p>O</p> <p> .</p> <p> . -. , :</p> <p> () HCOH</p> <p> () CH3CHO</p> <p> () 3CH3COCH</p> <p> ( ) 3CH3CH2COCHO 2CH3CH 3C CH</p> <p> . , .</p> <p> -. - . ) (Oxidation / . ) (Reduction- / . .</p> <p> . , </p> <p> ()</p> <p> 2- -2- ()</p> <p> R C H O RCH2OH</p> <p> OH C O 'RCHR</p> <p>R 'R</p> <p> Carboxylic acidsO R C OHO C OH</p> <p> :</p> <p> :</p> <p> . , - -COOH -CO2H</p> <p> :O C R OH R O C O++ H</p> <p> : 3HCl, H2SO4, HNO</p> <p> HCOOH CH3COOH CH3CH2COOH CH3(CH2)2COOH CH3(CH2)3COOH CH3(CH2)4COOH () () () () () ()</p> <p> : O-H </p> <p> .b.p )(0C 101 56 811 5.87 .m.p )(0C 4.8 89- 6.61 711- </p> <p> .</p> <p> )g/100g (200C 79.4 79.0</p> <p>.b.p)(0C101 811 141 461 681 502</p> <p>HCOOH CH3COOH CH3CH2COOH</p> <p> CH3(CH2)2COOH CH3(CH2)3COOH CH3(CH2)4COOH</p> <p> ( 4= )n . , , .</p> <p> O C R OH ][R R O C H ][R H OH C R H </p> <p> O + NaOH C OH R R O C +O- Na + H2O</p> <p> . : CH3(CH2)16COOH</p> <p> : SC_SOAP.gif</p> <p> O R C X</p> <p> :</p> <p> .</p> <p>X -OR -NRR -Cl</p> <p> 8</p> <p> O R C X</p> <p> :</p> <p> .</p> <p>X -OR -NRR -Cl</p> <p>O 'R C OR :O R C OH + R'OH O R C OR' + H2O</p> <p> :</p> <p> : ( ).</p> <p> :O 'R C OH + H-O-R+H</p> <p>O R C OR' + H2O </p> <p> . . , .</p> <p>O 2CH3CH2CH 3C OH + H-O-CH +H O 2CH3CH2CH 3C OCH + H2O</p> <p> . : . , , . . , .</p> <p> 3CH3(CH2)2-CO-O-CH 3CH3(CH2)2-CO-O-CH2CH 3CH3(CH2)2-CO-O-(CH2)4CH 3CH3-CO-O-(CH2)4CH 3CH3-CO-O-(CH2)7CH </p> <p> :</p> <p>O "R C NR'R .</p> <p>R N ''R - .H R N ''R +R' + H R N ''R ''R</p> <p>'R</p> <p> :</p> <p> :R-Cl + NH3 R-NH2 + HCl : CH3CH2CH2-Cl + NH3 CH3CH2CH2-NH2 + HCl</p> <p> , O R C OH + H N ''R 'R</p> <p>O R C NR'R" + H2O</p> <p> . .</p> <p> O 2CH3CH2CH 3C OH + H-NH-CH</p> <p>O 2CH3CH2CH C NHCH3 + H2O</p> <p>-N-</p> <p> . 22 . . : </p> <p> :H2N-CHR-COOH</p> <p> H2NCH2COOHH2NCHCOOH CH3</p> <p>glycine alanine </p> <p>) (O H2NCH2COOH + H2NCHCOOH CH3 CH3</p> <p>H2NCH2CNHCHCOOH + H2O</p> <p> Aromaticity : . : , . .</p> <p> Benzene : 6C6H - ( ): 4 : 3 ( ) - . 93.1 45.1 43.1 </p> <p> . 0021. : </p> <p> , :H H H H H H</p> <p> .</p> <p> () :3CH OH 2NH</p> <p> Toluene</p> <p> Phenol</p> <p> Aniline</p> <p>NO2NO2</p> <p>CH3 NO2</p> <p>Nitrobenzene </p> <p>NO26,4,2- 2,4,6-trinitrotoluene (TNT)</p> <p>O C</p> <p>OH</p> <p>O C</p> <p>OH OCCH3 O</p> <p>Benzoic acid </p> <p> Acetylsalicylic acid (Aspirin)</p> <p>Biphenyl 6 </p> <p>Naphthalene 5 </p> <p> . , , , . , . , . </p> <p> Br 2+ Br + HBr</p> <p> : 1.</p> <p>.</p> <p>.</p> <p>2. : . 23 C18H. 8C10H ?</p> <p>3. / , / :CH2=CH2 + Br2 CH3CH2CH3 + Cl2 CH3iii)</p> <p>i)</p> <p>ii)</p> <p>+ Cl2 </p> <p>iv)</p> <p>CH3CH2CH2OH + CH3COOH </p> <p>OCCH3v)</p> <p>O</p> <p>+ H2O </p> <p>vi)</p> <p>(CH3)2CHNH2 + CH3CH2CH2COOH </p> <p>Ovii)</p> <p>H2NCH2C NHCHCOOH CH3</p> <p>+ H2O </p> <p>viii)</p> <p>CH3CH2OH + CH3CHCH3 OH[O]</p> <p>ix)</p> <p>CH3CH2CH2OH </p> <p>4. :O CH2OH OH C 3OCCH O OH</p> <p>:E-A / C (C4H11N)NH3</p> <p>.5</p> <p>A (C4H8)</p> <p>HBr</p> <p>B (C4H9Br) </p> <p>OH</p> <p>D (C4H10O)</p> <p>O</p> <p>O</p> <p>C+E</p> <p>CH3CH2C-NH-C-CH3CH3</p> <p>D+E</p> <p>CH3CH2C-O-C-CH3CH3</p> <p> ' - 9</p> <p> )(Polymers - , . - . . : , , ' : , , '. , . </p> <p> - . . , . , .</p> <p> - . </p> <p> - . </p> <p> , . .</p> <p> - 03 - 91. Charles Goodyear . - 91 , , - .celluloid - 1907 - - . - 1912 ' - ,glyptal -, .</p> <p>0391 - - Du-Pont , , . 8391 - - Dow . 9391 - - ( ICI) . 0591 - Ziegler - Natta - , , .</p> <p>0791-0691 - high performance . " . () ?...</p>