أساسيات الكيمياء العضوية - نظري

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ ،‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬ .١ K‫א‬‫א‬ .٢ K‫א‬‫א‬‫א‬‫ א‬.٣ K‫א‬‫א‬CH2 = CHCH2CH3 .٤  W‫א‬‫א‬‫א‬  K٪٩٠‫א‬‫א‬‫א‬  W‫א‬‫א‬  K٤  W‫א‬‫א‬  KOverhead Projector .١ K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢ K .٣  W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬ - ٤١ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W١ J٣ ‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬  ‫א‬  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ E‫א‬‫א‬‫א‬‫א‬F‫א‬EAromatic) ‫א‬‫א‬  ، JOCH3 ‫א‬ ‫א‬‫א‬  JC6H5‫א‬‫א‬ J J J J JCOOCH3، JCOOH ، JC6H5‫א‬‫א‬‫א‬ EF‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬  W‫א‬٢ J٣ ‫א‬‫א‬‫א‬‫א‬‫א‬C6H6‫א‬  ‫א‬  ،   ‫א‬K ‫א‬ ‫א‬‫א‬ ‫א‬    ‫א‬  ‫א‬K ‫א‬sp2‫א‬‫א‬،‫א‬‫א‬‫א‬ C=C‫א‬‫א‬‫א‬، (A˚١٣٩F‫א‬‫א‬– ‫א‬‫א‬KE١٥٤A˚)C-C‫א‬‫א‬‫א‬،E١٣٢A˚)  WKekule ‫א‬‫א‬  II  I ‫א‬Hybrid‫א‬‫א‬KII،I‫א‬  ‫א‬‫א‬‫א‬‫א‬KII،I  Delocaized - ٤٢ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬٣ J٣  W‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ K١ FP‫א‬‫א‬‫א‬EF KE‫א‬ K‫א‬ K٢ K‫א‬‫א‬‫א‬ K٣ ‫א‬‫א‬‫א‬EHuckels ruleF K٤ En = 0,1,2,3KKKKKKKFE4n+2)‫א‬‫א‬π‫א‬‫א‬ ‫א‬Eπ‫א‬F‫א‬‫א‬ WE٦F‫א‬‫א‬E١Fn‫א‬   (4x1+2) = 6 E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬   W‫א‬     Anthracene  Benzen Naphthalene n =3  n =1 n =2    N.. ..  N Pyridine Pyrole - ٤٣ - n =1

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  Phenanthrene n =1 4(1)+2=6 πes + n=3 4(1)+2=6 πes  4(3)+2=14 πes  - n =1 + 4(1)+2=6 πes    n = 0  n =1 4(0)+2=2 πes 4(1)+2=6 πes  W‫א‬‫א‬‫א‬  -+  W‫א‬‫א‬‫א‬٤ J٣ ‫א‬‫א‬º٨٠K‫א‬،‫א‬‫א‬  ‫א‬‫א‬ ‫א‬‫א‬º٤{٥ ‫א‬   Kπ‫א‬‫א‬  W‫א‬٥ J٣  ‫א‬‫א‬‫א‬‫א‬   W‫א‬ W‫א‬‫א‬‫א‬‫א‬‫א‬ K١  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ - ٤٤ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ Br I  CH2CH3    Bromobenzene Iodobenzene Ethylbenzene NO2   W‫א‬ Nitrobenzene CH=CH2 CH3_ CH_ CH3 CHO CH3     Toluene Benzaldehyde Styrene  Cumene OH NH2 COOH O C_ CH3    Phenol Benzoic acid   Aniline Acetopnenone SO3H OCH3   Benzenesulfonic acid Anisole - ٤٥ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ ‫א‬،‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬‫א‬phenyl CH3CHCH2CH3 CH2CH2OH    2-Phenylbutane 2-Phenylethanol Benzyl‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬،Benzal‫א‬‫א‬  KBenzo   CH2Cl CHCl2 CCl3    Benzylchloride  Benzalchloride  Benzotrichloride ‫א‬ K٢ ortho EOF‫א‬‫א‬‫א‬K‫א‬‫א‬ ‫א‬  meta EmF ‫א‬ ‫א‬    ‫א‬ ‫א‬   ‫א‬   Kpara Ep F ‫א‬ ‫א‬   ‫א‬ Benzene.‫א‬K‫א‬‫א‬ W‫א‬‫א‬،‫א‬‫א‬،‫א‬ CI CH2CH3 F CI    CI  I  O-dichlorobenzene m-chloroethylbenzene p-fluoroiodobenzene - ٤٦ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ CH 3 COOH OH CI   NO 2  Br  m-nitrotoluene m-bromobenzoic acid o-chlorophenol  W‫א‬‫א‬CH3- CH3 CH3 CH3 CH 3    CH3   CH 3  o-xylene  m-xylene  p-xylene  ‫א‬‫א‬ CI 1NO2 CI 1 2 CI 62 3 53 64  F 4 CI  5    3-chloro-5-fluronitrobenzene  1,2,3-trichlorobenzene ‫א‬F  E١‫א‬     (1,2,6-trichlorobenzene)  OH NO26 1CH32NO2 Br Br 53   Br 4    NO2 2,4,6-tribromophenol  ‫א‬) 2,4,6-trinitrotoluene (TNT) E١‫א‬ ‫א‬F  E١‫א‬ - ٤٧ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬٦ J٣ ،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬ ‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬   ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬،  K‫א‬ Al2O3_CrO3/ 500ْ C CH3 Pt/ 400ْ C CH3(CH2)5CH3 + 3H2  Toluene K CH3 Al2O3_ Pt + 3H2 550 Cْ Benzene     W‫א‬‫א‬٧ J٣ ‫א‬‫א‬‫א‬،‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬   W‫א‬ - ٤٨ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  WHalogenation‫א‬ K ‫א‬، ‫א‬  ‫א‬‫א‬،‫א‬‫א‬E‫א‬‫א‬‫א‬F‫א‬ ،E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬، ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬   ‫א‬    K  ‫א‬   ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬ CH2Cl CHCl2 CCl3 Cl2 Cl2 Cl2 CH3 ‫ﺿﻮء‬ ‫ﺿﻮء‬ ‫ﺿﻮء‬ Benzoyl Benzoal Benzotrichloride chloride CH3 chloride CH3 Toluene Cl Cl 2/FeCl 3 +  o-chlorotoluene p-chlorotoluene  W‫א‬‫א‬ K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K   ‫א‬‫א‬‫א‬ ‫א‬  K  - ٤٩ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ CH3 COOH KMnO4 or K2Cr2O7  Benzoic acid CH2CH2CH3 COOH CH3 KMnO4 or COOH K2Cr2O7 + (CO2 + H2O) Phthalic acid   ( 1,2- benzenedicarboxylic acid) W‫א‬ .١ W‫א‬ -‫أ‬ ،‫א‬‫א‬‫א‬ EthylbenzeneK‫א‬،‫א‬‫א‬‫א‬  KCyclohexane  CH2CH3 Ni,Pt or Pd CH2CH3 + 3H2  Ethylbenzene Ethylcyclohexane  W‫א‬‫א‬‫א‬‫א‬ J ‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬  ، ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬ ،‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬، ، ‫א‬‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ - ٥٠ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ Alkylation E‫א‬–F  J١ + CH3Cl AlCl3 CH3 + HCl   AcylationE‫א‬–F  J٢ O O + CH3_ C _ Cl AlCl3 C _ CH3   Halogenation‫א‬  J٣  + Br2 FeBr3 Br  Nitroation‫א‬  J٤ + HNO3 H2SO4(conc.) NO2  ‫א‬  J٥ + H2SO4 SO3 SO3H Sulfonation - ٥١ - 

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬‫א‬٨ J٣ ، ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬ AnisoleK‫א‬‫א‬،‫א‬ Knitroanizole ‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬ OCH3 OCH3 OCH3 HNO3 NO2 H2SO4 +   NO2  ‫א‬‫א‬ ‫א‬‫א‬–‫א‬  K‫א‬ NO2 NO2 HNO3 NO2 H2SO4  =O،R+F‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬ ‫א‬EH+،Br+،NO2+،CH3C+ ‫א‬‫א‬‫א‬‫א‬،‫א‬  ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬  W‫א‬  ‫א‬–‫א‬ .١  W‫א‬‫א‬‫א‬‫א‬  -NH2(-NHR,-NR2) ,-OH >-OR,-NHCOCH3 > -C6H5 ,-R  K‫א‬ERF K‫א‬‫א‬–‫א‬ .٢ - ٥٢ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  E-F,-Cl, - Br) W‫א‬‫א‬K‫א‬ .٣  K-NO2, -N+(R)3,-C=N,COOH( -COOR ),-SO3H,-CHO,-COR    W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬،‫א‬   K‫א‬‫א‬‫א‬ NO2 NO2 HNO3 Br2,Fe H2SO4 Br m-bromonitobenzene Br Br Br Br2,Fe HNO3 NO2 H2SO4 + NO2 o-bromonitro p-bromonitro   benzene (38%) benzene (62%)  W‫א‬‫א‬‫א‬٩ J٣ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬K‫א‬ ‫א‬K‫א‬،‫א‬‫א‬،EF ‫א‬‫א‬KE‫א‬F‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬، K‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ - ٥٣ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬    W‫א‬‫א‬‫א‬W١  CH = CH 2 COOH CH3 a) Br b) c) NO2 CH3 CH3 COOH CI d) e) II NO 2   W‫א‬‫א‬‫א‬‫א‬‫א‬W٢ a) 1,3,5-trichloro benzen b) m-bromotoluene c) p-bromonitro benzene d) lsopropyl benzene e) 4-bromo-2,3-dinitrotoluene f) m-chloro benzoic acid   W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W٣  CH(CH 3)2 - KMnO 4 / OH   CH 3 Br 2 /hv - ٥٤ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ NO 2 AICI 3 Br2 FeBr 3 OC2H5 + CH3CH2CI CI AICI 3 O + CH 3 C - CI CH 3 H2O3 HNO 3 + CH3 CHCI CH 3 AICI 3 CN Br 2 FeBr 3          - ٥٥ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  ٣ J٨  W١ CH3 O-Bromostyrene  J‫א‬ 3,5- Diiodo toluene J   W٢  Br  CH (CH3)2    W٣ CH(CH 3)2 COOH CH (CH3)2 KMnO4/OH-    NO2 NO2  Br 2 Br  CH3 FeBr3 CH3 CH3 HNO 3 NO2 H2SO4 +  NO2 + CH3 CHCI CH3 AICI3  - ٥٦ -



 ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬ ٤



 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬  W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬ .١ K‫א‬‫א‬‫א‬‫א‬‫א‬ .٢ K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣  W‫א‬‫א‬‫א‬  K٪٨٠‫א‬‫א‬‫א‬  W‫א‬‫א‬  K  W‫א‬‫א‬  KOverhead Projector .١ K‫א‬‫א‬ .٢ K .٣  W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬ - ٥٧ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  W١ J٤ ،  ‫א‬‫א‬‫א‬‫א‬  R،R - X‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬،X،  K‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬  W‫א‬‫א‬‫א‬٢ J٤ ،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K‫א‬‫א‬‫א‬‫א‬W‫א‬‫א‬ ‫א‬F‫א‬Alkyl‫א‬‫א‬‫א‬ ‫א‬‫א‬E F‫א‬IUPAC‫א‬‫א‬،E  W‫א‬‫א‬   CH3Cl CH3CH2CH2Br 1˚ halides  (Methyl chloride) (n – propyl bromide) Chloromethane ‫א‬ 1 - Bromopropane  CI I CH3 - CH - CH3 (Cyclopentyl chloride) 2ºhalides EIsopropyl iodide) ‫א‬ 2- Iodopropane Chlorocyclopentane CH3 CH3 CH3 - CH2 - CH2 - C - CH = CH2 CH3 - C - CH3 3º h alides Br Br ‫א‬ 3-Bromo-3-methyl-1-hexene (tert-Butyl bromide)  W‫א‬‫א‬‫א‬‫א‬ - ٥٨ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ CH2 = CH_ CH2 CH2 = CH CH2X Benzylhalide X X Allylhalide Vinylhalide   W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  CCl4 CHCl3 CH2Cl2 (Carbontetrachloride) (Chloroform) (Methylene chloride) Tetrachloromethane Trichloromethane Dichloromethane CHBr3 CHI3 Br (Bromoform) (Iodoform) CH3 - C - CH2CH3 Br 2,2-Dibromobutane  W‫א‬‫א‬‫א‬٣ J٤ ‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬ ‫א‬‫א‬F‫א‬‫א‬‫א‬K‫א‬  K‫א‬E‫א‬  W‫א‬‫א‬‫א‬٤ J٤ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   W - ٥٩ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F‫א‬‫א‬‫א‬‫א‬‫ א‬.١ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬ CH3CH3 Cl2 CH3CH2CI + HCI + ... UV or heat ‫ﺿﻮ او ﺣﺮارة‬ CH3 - CH = CH2 Br2 CH2 - CH = CH2 + HBr UV or Br  ‫א‬‫א‬‫א‬‫א‬ .٢ ‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬   W‫א‬‫א‬ CH3 - CH = CH2 HCl CH3 - CH - CH3 CCl4 Cl ‫א‬‫א‬  W‫א‬‫א‬ HBr CH3CH2CH2 Br CH3-CH = CH2 R-O-O-R   ‫א‬  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W CH CH HCl CH2 = CH HCl CH3CHCl2 CCl4 Cl CCl4 - ٦٠ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F‫א‬‫א‬‫א‬‫ א‬.٣ ‫א‬HX‫א‬‫א‬‫א‬‫א‬‫א‬   W‫א‬EPCl5 , PCl3 , PBr3F‫א‬‫א‬SOCl2‫א‬  CH3(CH2)5 CH2OH HCl CH3(CH2)5 CH2 +H2O ZnCl2 / 150ْ Cl CH3CH2OH + SOCl2 NR3 CH3CH2Cl + SO2 + HCl CH3CH2OH +PBr3 CH3CH2Br + P (OH)3   W‫א‬‫א‬٥ J٤ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬KE‫א‬F‫א‬‫א‬ KE‫א‬F‫א‬  KKKK‫א‬‫א‬  Nucleophilic substitution reactions‫א‬‫א‬‫א‬ K١   ‫א‬‫א‬‫א‬‫א‬      E ‫א‬ ‫א‬‫א‬F  ‫א‬ ‫א‬   ‫א‬‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ R3Cδ+χδ- R3C-Nu + χ –  W‫א‬‫א‬‫א‬‫א‬ - ٦١ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ S- R S-H O - - , , CH3NH2 , NH3 , - O - C - R , OR ,OH .. CN - ,R - C = C - N (CH3)3 , HN (CH3)2 ,  ‫א‬،‫א‬‫א‬ ‫א‬‫א‬   W‫א‬ ‫א‬  CH3CH2CH2Br KOH CH3CH2CH2OH H2O Elemination reactionsEEFE‫א‬‫א‬F‫א‬ K٢ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬E‫א‬‫א‬‫א‬‫א‬F‫א‬ _ KOH (Or) CH3CH2O - Na+CH3 EtOH / CH3CH CH3 - CH = CH2 Br -4‫א‬‫א‬ K٣ Grignard formation K  K‫א‬‫א‬‫א‬‫א‬‫א‬  CH3CH2CH2Br + Mg ether CH3CH2CH2MgBr  ‫א‬ ‫א‬             K،‫א‬‫א‬‫א‬‫א‬‫א‬  - ٦٢ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  ‫א‬ K W‫א‬‫א‬ CH3CH2CH2Br + 2Li CH3CH2CH2-Li++ LiBr  K‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬٦ J٤ ‫א‬‫א‬‫א‬‫א‬‫א‬   KD.D.T.‫א‬ H Cl C Cl CCl3   D.D.T  ‫א‬‫א‬‫א‬–[CF2–CF2]nTeflonW‫א‬  ‫א‬–[H2–CCl2]n–‫א‬‫א‬‫א‬‫א‬‫א‬ K ‫א‬‫א‬‫א‬‫א‬–[CH2 – CHCl2-]n–PVC K‫א‬ CCl3FCCl2F2‫א‬CF3CHClBr‫א‬HCX3haloform‫א‬ ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬  Antifungus‫א‬Antibiotics‫א‬‫א‬‫א‬  - ٦٣ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬    EIUPAC F‫א‬‫א‬‫א‬‫א‬W١  Br E CH3CH_CH_ CH3   Br CH3 E  NO2  E CH3_ CH2_ CH=CH 2 E  CH _ CH3  Cl Cl    CH2 = CH CH2Cl E    E3◦ 2◦1◦F‫א‬‫א‬‫א‬W٢  CH3 E Cl CH3 Br E CH3 C CH3  Cl  E    K‫א‬‫א‬‫א‬‫א‬W٣  CH3 HCl E CH3CHOH ZnCl2 CH3 HBr E E  Br2 hv CH3 CH3CHCH3 CH2CH3 Cl2  hv  OH SOCl2 E - ٦٤ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬ CH3CH2CH_ CH3 Na+O-CH2CH3 E CH3CH2OH  Br  Br E KOH E CH3 C CH2 EtOH CH3 CH3CH2CH2Cl NH2CH3 CH2CH2Br CH3C C-Na+ CH3CH_ CH3 KOH E EtOH / Br E CH3CH2CH2Br + Mg ether  OH-  W‫א‬‫א‬‫א‬‫א‬W٤ CH3CHBrCH 3 ethanol  OH-  E١ CH3CHBrCH 3 H2O  E٢ (CH3)3CBr CN -  E٣ ethanol  E٤ (CH3)3CBr H2O             - ٦٥ -

 ‫א‬‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬‫א‬‫א‬  ‫א‬‫א‬ ‫א‬  ‫א‬   W١ 2-Bromo-3-methyl butane – ‫أ‬ 1-Bromo-2-Nitro cyclohexane -‫ب‬ 1-chloro-1-butene - ‫ﺟـ‬   W٢ 3◦ E 2◦ E  1◦ E   W٣ CH3 HCl CH3 E CH3CHOH ZnCl2 CH3CHCl + H2O E CH3 Br2 CH3 E CH3CHCH3 hv E CH3 C CH3 Br  CH3CH2CH2Cl NH2CH3 CH3CH2CH2NHCH3 KOH CH3CH_ CH3 EtOH / CH3CH=CH 2 + HBr Br  W٤ ‫א‬‫א‬ J١ ‫א‬‫א‬ J٢ ‫א‬‫א‬ J٤   - ٦٦ -



‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬ ٥



‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬   W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬ .١  K‫א‬‫א‬‫א‬‫א‬ .٢ K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٣   W‫א‬‫א‬‫א‬  K٪80‫א‬‫א‬‫א‬  W‫א‬‫א‬  K   W‫א‬‫א‬  KOverhead Projector .١  K‫א‬‫א‬‫א‬ .٢ K .٣   W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬ - ٦٧ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W١ J٥  JOH‫א‬‫א‬  ‫א‬‫א‬‫א‬،ArOH‫א‬‫א‬،ROH‫א‬‫א‬‫א‬  Ar  ‫א‬R ،ArR‫א‬‫א‬ ،SP3‫א‬‫א‬ ‫א‬،   KSP2       ‫א‬ ‫א‬    ‫א‬‫א‬‫א‬، ‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬K‫א‬ ‫א‬K‫א‬‫א‬  K‫א‬  W‫א‬٢ J٥ ‫א‬ ‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬     Tertiary 3O Secondary 2O Primary 1O R H H R C OH R C OH R C OH R R H  ‫א‬ ‫א‬   ‫א‬ ‫א‬   ‫א‬ ‫א‬     JOH    JOH    JOH   ‫א‬             K‫א‬ KR‫א‬ K‫א‬ - ٦٨ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬٣ J٥ ‫א‬KIUPAC‫א‬‫א‬‫א‬‫א‬،  K‫א‬‫א‬‫א‬‫א‬  W‫א‬‫ א‬K١  W‫א‬‫א‬‫א‬‫א‬   CH3 OH  CH3CH2OH CH2=CH-CH2OH  Methyl alcohl  Ethyl alcohol Allyl alcohol CH3 CH3 CH CH3 OH CH3 c CH3 Tert-Butyl alcohol OH CH2OH Isopropyl alcohol OH Cyclopentyl alcohol Benzyl alcohol  WE‫א‬FW‫א‬‫ א‬K٢  JOH‫א‬‫א‬ K١ EeF‫א‬‫א‬‫א‬‫א‬ ‫א‬ CH3OHCH3CH2OHWK Jol  MethanolEthanol  - ٦٩ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ -OH‫א‬‫א‬‫א‬‫א‬ K٢ ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬E١F‫א‬‫א‬‫א‬ CH3CH2CH2OH CH3CH2CH2CH CH3 1-Propanol OH OH 2-Pentanol C2H5 CH3CH2CHCH2CHCH3 Cyclohexanol OH 4-Ethyl-2-hexanol CH2CH2Br CH3CH2CH2CHCH2 OH 2-(2-Bromoethyl)-1-Pentanol  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣ ‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬ CH2 CH CH CH CH3 CH3CH CH2CH3 OH CH3 C CH2 4-Methyl-1-Penten-3-ol OH CH C CH CH3 3-Ethyl-3-buten-2-ol OH OH CH3 3-Butyn-2-ol 4-Methyl-2-cyclohexenol - ٧٠ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  -ol  ‫א‬tetra,tri ,di‫א‬‫א‬‫א‬ K٤  KK‫א‬   CH2 CH2 CH2 CH CH2   OH OH OH OH OH  1,2-Ethanediol 1,2,3-Propantriol  Ethylene glycol Glycerol or Glycerene  W‫א‬   ‫א‬  ‫א‬     ‫א‬     ،     ‫א‬  -OH     ،  ،‫א‬‫א‬‫א‬  W‫א‬‫א‬ OH OH OH Phenol Br NH2 OH m-Bromophenol p-Aminophenol COOH OH o-Hydroxybenzoic OH acid ( Salicylic acid) Hydroquinone - ٧١ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬‫א‬‫א‬٤ J٥ ‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬ ‫א‬  ‫א‬ ‫א‬     ‫א‬    ‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬  K‫א‬‫א‬،EF‫א‬‫א‬ O R Ar Ar RH O O O H H H   ‫א‬ ‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬ Ethanol Propane ‫א‬‫א‬  L٤٦  °٧٨ L٤٤  °٤٢ ‫א‬ ،‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬  K‫א‬ o HR RH oo HH   ‫א‬ - ٧٢ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬٥ J٥  W‫א‬ K ،‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬ OH CH3CH = CH2 + H2O H+ CH3 CH CH3 Propene  2-Propanol ‫א‬،Ethanol ‫א‬Methanol‫א‬‫א‬  W   water gas‫א‬‫א‬‫א‬‫א‬W‫א‬ K  KE‫א‬‫א‬F O C +H2O 1300 C CO + H2 ‫א‬‫א‬Water gas  K300 atm300c‫א‬‫א‬ CO + H2 + H2 Zn + Cr 2 O3 as Cat. CH3OH Water gas  WNatural gas‫א‬‫א‬ K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K900 Co CH4 + H2O Ni as Cat. CO + 3H2O  K‫א‬‫א‬‫א‬Synthesis‫א‬‫א‬‫א‬ CO + H2O ZnO + Cr2 O3 as Cat. CH3OH O 300C , 300 atm.  - ٧٣ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬         ‫א‬  K : Ethyl hydrogen sulphate٨٠Co‫א‬ CH2 CH2 + H2SO4 CH3 CH2 O SO2 OH  K‫א‬ CH3 CH2 O SO2 OH + H2O CH3 CH2 OH + H2SO4  ‫א‬ ‫א‬ ‫א‬   ‫א‬ ‫א‬  K Phosphoric F‫א‬‫א‬ Co‫א‬E‫א‬‫א‬acid on silca  K70 atm٣٠٠  W‫א‬ K ‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬ SO3H O- N+a OH NaOH HCl Benzene sulfonic acid Sodium phenoxide Phenol  W‫א‬‫א‬ ،Propene ‫א‬‫א‬‫א‬‫א‬ ،Cumene‫א‬ E١ AlCl3‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬  K‫א‬‫א‬ + CH3 CH CH2 CH CH3 CH3 Cumene - ٧٤ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬‫א‬Hydroperoxide ‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬‫א‬ CH3 OH CH CH3 C CH3 +H+ ( CH3)2 C O O OH CH3 + O2 Phenol Acetone   K‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ E٢ Cl - N+a + OH Cl2 O H o NaOH 40 C o Chlorobezene 330 C Benzene Sodium phenoxide Phenol  W‫א‬‫א‬٦ J٥  W‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬-١ ‫א‬،‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬،‫א‬ 2CH3CH2OH H2SO4 (CH3CH2) 2 + H2O O 140 C Ethanol Diethyl ether CH3CH2OH H2SO4 CH2 CH2 + H2O O 180 C  Ethylene  K‫א‬‫א‬‫א‬‫א‬‫א‬  WOxidation‫א‬ ،‫א‬‫א‬‫א‬E1F‫א‬‫א‬ ‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬،‫א‬ - ٧٥ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ Cu/ CH3CHO Acetaldehyde CH3CH2OH CrO3 or Pyridine O Ethanol (1) CH3CH2OH H2Cr2O7 CH3COOH + 3+ Cr Acetic acid OH O CH3CHCH3 H2Cr2O7 CH3 C CH3 o or Cu / Ketone Alcohol ( 2 )  OH Oxid Agent CH3 C CH3    CH3 W‫א‬‫ א‬-٢ ‫א‬‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬  K‫א‬ CH3 OH + Na CH3 - N+a + 1 H2 O 2 Methanol Sodium Methoxide OH - N+a O + Na + 1 H2 2 Phenol - ٧٦ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ -٣ K‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬  K‫א‬ H+‫א‬ O + (Ar)R OH + RCOOH H (Ar)RO C R + H2O Alcohol or Phenol Ester + CH3COOH+ CH3CH2OH H CH3COOCH2CH3 + H2O Acetic acid Ethyl alcohol Ethyl acetate  - ٧٧ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F E١  WE3FE2FE1F‫א‬‫א‬‫א‬‫א‬ (A CH3 CH2 CH2 OH (B CH2CH3 CH3 CH2 C OH Br (D CH3  CH2CH3 (C CH3 CH CH2  H2C C CH2 OH OH  W‫א‬‫א‬ E٢ OH (A CH2O H (B OH (c OH (D CH3 CH3 Br OH  E٣  CH3   NH2  OH  W‫א‬‫א‬ CH3 CH CH2CH3 (A   OH CH3 C CH2CH3 O O (B   CH3 CH2 C OH + CH3OH   CH3 CH2 CH2 OH Cu , + H OH + K2Cr2O7  ? (C H2SO4 ? (D OH (E  - ٧٨ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬‫א‬‫ א‬E٤ 1) 2,4-Dimethyl-2-Octanol. 2) Cyclopentane-1,4-diol.  3) 2,2,2-Trichloroethanol.  4) 2-Butene-1,4-diol.  5) 3-Bromo-2-nonanol.  6) O- Bromophenol.  7) 2,4,6-Trichlorophenol  8) p-Hydroxybenzyl alcohol.            - ٧٩ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F  WE1F‫א‬‫א‬  K3o،  1,1-Diethyl propanol EA .2o، 1-Bromo-2-propanol (D  WE2F‫א‬‫א‬  4-Amino-5-bromo phenol EA 2,4,6-Trimethyl phenol EC  WE3F‫א‬‫א‬ KMnO 4 (A  H2O (B O (C  CH3 CH2 C O CH3  WE4F‫א‬‫א‬ O  CH3 CH2 C H CH3 (1 CH3-CH2-CH2-CH2-C-CH2-CH-CH3 CH3 OH  CCl3-CH2-OH (3 (5 CH3-CH2-CH2-CH2-CH2-CH2-CH-CH-CH3 (7   Br OH OH Cl Cl  Cl  - ٨٠ -



‫א‬‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ٦