أساسيات الكيمياء العضوية - نظري

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬ .١ K‫א‬‫א‬‫א‬‫א‬ .٢   W‫א‬‫א‬‫א‬  K٪80‫א‬‫א‬‫א‬   W‫א‬‫א‬  K   W‫א‬‫א‬  KOverhead Projector .١ K .٢   W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬  - ٨١ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W١ J٦  R/RR-O-R/‫א‬‫א‬‫א‬‫א‬   WK ‫א‬‫א‬‫א‬،R/R‫א‬‫א‬  K‫א‬  W‫א‬‫א‬٢ J٦ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   ‫א‬ ‫א‬ ‫א‬،Ether  K‫א‬ CH3OCH2CH3 CH3CH2OCH2CH3 CH3OCH3 Ethyl methyl ether Ethyl ether Methyl ether o CH3 o Methyl phenyl ether Phenyl ether ( Anizole ) -O-R، IUPAC ‫א‬‫א‬‫א‬‫א‬  ‫א‬، ‫א‬REAlkoxy)‫א‬  W‫א‬‫א‬R(Aryloxy) Br oCH2CH3 CH3CH2CHCH3 p-Bromophenoxy ethane oCH3 2-Methoxy butane oCH2CH3   Ethoxy cyclohexane  ‫א‬‫א‬‫א‬oxa‫א‬  W‫א‬‫א‬‫א‬‫א‬K‫א‬ - ٨٢ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ 1 2 34 56 7 8 9 CH2 O CH2CH2 O CH2CH2 O CH3 Cl 1-Chloro-2,5,8 -trioxanonane   W‫א‬‫א‬ O o o O 1,4-Di oxane Oxlane Oxane or or or Tet rahydr ofuran Tetrahydropyran 1,4-Dioxa cyclohexane ( THF ) o CH2 CH2 o Oxiran e cepoxide Oxetane or or Trimethylene oxide   Ethylene oxide  W‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬ ، ‫א‬‫א‬  K ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬،‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬ K‫א‬‫א‬،‫א‬،‫א‬‫א‬‫א‬‫א‬  ‫א‬،‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ - ٨٣ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ R H O OR R HO  R  W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫ א‬‫א‬ ‫א‬‫ א‬‫א‬ ‫א‬  o78 46 Ethanol CH3CH2OH   o24 J 46 Methylether CH3OCH3   o42 J 44 Propane CH3CH2CH3  W‫א‬‫א‬‫א‬٣ J٦ ‫א‬‫א‬F‫א‬‫א‬‫א‬  ، ‫א‬‫א‬‫א‬ E‫א‬‫א‬‫א‬  K ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬EPeroxide)‫א‬(‫א‬‫א‬‫א‬F  K ‫א‬‫א‬‫א‬‫א‬  ،Fe+++‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬FeSO4  W‫א‬‫א‬‫א‬‫א‬ - ٨٤ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  Peroxide + Fe+++ - Fe(SCN)3 SCN    W‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬F‫א‬‫א‬ .١  KE‫א‬‫א‬ K‫א‬‫א‬‫ א‬.٢ K‫א‬‫א‬‫א‬‫א‬‫ א‬.٣  W‫א‬‫א‬٤ J٦  W‫א‬‫א‬‫א‬W  ‫א‬‫א‬‫א‬W‫א‬‫א‬‫א‬‫ א‬.١ ‫א‬ ‫א‬    ‫א‬ K  ‫א‬   ‫א‬ CH3CH2OH H2SO4  K‫א‬‫א‬ 140 CH3CH2OCH2CH3  W .٢ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  F‫א‬‫א‬،Ealkoxide ion‫א‬F‫א‬  K‫א‬‫א‬‫א‬Ephenoxide ion‫א‬ CH3 CH - Na+ + CH3CH2Br CH3 CH O CH2CH3 O CH3 CH3 Ethyl isopropyl ether  - ٨٥ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ - N+a O CH3 O + CH3Br Anizole  W‫א‬‫א‬‫א‬W  W‫א‬‫א‬‫א‬‫ א‬.١  K‫א‬‫א‬‫א‬‫א‬ W‫א‬Diethyl ether .٢   ‫א‬  ‫א‬    ‫א‬  ‫א‬   K‫א‬‫א‬  W‫א‬‫א‬٥ J٦ ، ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬ CH3 CH2 O CH2 CH3 + 2HI + H 2CH3 CH2-I + H 2O  Iodoethane        - ٨٦ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F C6H5CH2 O C3H7 E4  W‫א‬‫א‬ .١ CH3CH2CH2OCH2CH3E1 CH3 CH CH2 CH CH3 (5 (CH3CH2CH2CH2)2OE2 CH3 O CH2CH3 (6 CH3 O CH CH3 (3 CH3 OCH2 CH3  1) Diisopropyl ether.  W‫א‬‫א‬‫א‬‫ א‬.٢ 3) tert-Butyl methyl ether. 5) Phenyl ether. 2) Diallyl ether. 4) Benzyl ether. 6) 4-Ethoxy -2-Methylhexane.  W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣ CH3 (1) + (2) CH3 C O CH2 (1  CH3 O- (3) (2 (4)   CH3O + (CH3)3CBr (3 (5) (CH3)C O-  O + CH3I  (4 (CH3)2CHCH 2OC(CH 3)3 HI acid conc. with  - ٨٧ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  K‫א؟‬‫א‬‫א‬ .٤ CH3CH2CHCH2CH2CH3 (2   CH3CH2CH2CH2CH2CH2CH3 (1  OH    CH3CH2CH2 O CH2CH2CH3 (3                        - ٨٨ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F WE1F‫א‬‫א‬ Dibutyl ether (3 Ethyl propyl ether (1 Isopropyl methyl ether (5  WE2F‫א‬‫א‬ CH3 O C (CH3)3 (2 (CH3)2 CH O CH (CH 3)2 (1 CH3-CH-CH 2-CH2-CH-CH 3 (6 CH3 O C2H5  WE3F‫א‬‫א‬ (CH3)3 C O CH3 (2 (CH3)3 C O CH3 (3   - ٨٩ -



 ‫א‬‫א‬‫א‬ ‫א‬‫א‬  ‫א‬‫א‬‫א‬ ٧



 ‫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‫א‬  W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬ .١  K‫א‬‫א‬‫א‬‫ א‬.٢  K‫א‬‫א‬‫א‬‫א‬‫א‬ .٣  W‫א‬‫א‬‫א‬  K٪80‫א‬‫א‬‫א‬   W‫א‬‫א‬  K  W‫א‬‫א‬  Overhead Projector. .١  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ .٢  W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬     - ٩٠ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W١ J٧ ‫א‬K C=O ‫א‬‫א‬‫א‬‫א‬ O EArF،R R(Ar)-C-H W ‫א‬‫א‬ O  R , R  R C R W‫א‬‫א‬‫א‬K  K  W‫א‬‫א‬‫א‬٢ J٧  KIUPAC‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬  W‫א‬‫א‬  W‫א‬‫א‬ J   Jic acid‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬aldehydeE‫א‬‫א‬‫א‬F  K‫א‬  O  ‫א‬‫א‬ Formic acid HCH   Formaldehyde O CH3 C H  ‫א‬‫א‬  Acetic acid   Acetaldehyde  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  (C C C C O)  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ - ٩١ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ CH2CH3 O CH3 CH CH C H B   CH3 α,β -Dimethyl Valeraldehyde  W‫א‬ J F‫א‬‫א‬‫א‬ ‫א‬‫א‬   Wketone‫א‬E‫א‬‫א‬ OO CH3 C CH3 CH3 C CH( CH3)2 Dimethyl ketone   Methyl isopropyl ketone   ( acetone ) Phenyl ‫א‬‫א‬‫א‬phenone‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬E-oic acid F-ic acid OO C CH3 C   Acetophenone  Benzophenone  W‫א‬‫א‬  W‫א‬‫א‬ J  ، ‫א‬‫א‬ Jal‫א‬‫א‬‫א‬ Je ‫א‬‫א‬‫א‬ –KK ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬K‫א‬‫א‬‫א‬  W‫א‬‫א‬ - ٩٢ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ O CH3 O CH3 C H CH3 CH CH2 C H   Ethanal  3-Methyl butanal ‫א‬ ‫א‬‫א‬  K‫א‬ OO CH CH   Benzaldehyde CH3  p-tolualdehyde  W‫א‬– ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬ Je‫א‬E Jal F Jone ‫א‬،‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬ ‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬  K‫א‬‫א‬ OO O CH3 C CH3 CH2 CH C CH3  Propanone  Cyclopentanone  3-buten-2-one  W‫א‬‫א‬‫א‬‫א‬‫א‬٣ J٧  ‫א‬ ‫א‬‫א‬ ‫א‬      ‫א‬‫א‬ ‫א‬ ‫א‬  ‫א‬‫א‬‫א‬‫א‬ C+=O- ‫א‬ ‫א‬‫א‬‫א‬،‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ - ٩٣ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  ‫א‬     ‫א‬ ‫א‬ ‫א‬ ‫א‬‫א‬ ‫א‬ K    K‫א‬ CO O HH    ‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬ Formalin‫א‬،‫א‬‫א‬‫א‬‫א‬  ‫א‬K‫א‬‫א‬،E٪37F ، ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬ ‫א‬، ‫א‬‫א‬، 56  K‫א‬‫א‬  W‫א‬‫א‬‫א‬٤ J٧  W‫א‬‫א‬‫א‬‫א‬–   W‫א‬ K ، ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬K‫א‬ O CH3CH2CH2OH Cu / CH3CH2C H o Propanal +3   1-Propanol (1) O Cr OH CH3C CH3 + CH3CHCH 3 H2Cr2O7 Acetone o    2-Propanol (2)  - ٩٤ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ K ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬E  ‫א‬F‫א‬  W‫א‬‫א‬‫א‬ O O + CH3CH2C Cl AlCl3 C CH2CH3 + HCl   Ethyl phenyl ketone  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬ J  W‫א‬‫א‬‫א‬ K١ ‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ O (1 2CH3OH + O2 CuO-Ag 2H C H + 2H2O  O 500-650 C PdCl2 O (2 H2O CH3 C H CH2 CH2 + 1/2O2   W‫א‬‫א‬ K٢  K‫א‬500 CO‫א‬‫א‬2-propanol‫א‬‫א‬ O (CH3)2CHOH Cu as Cat. CH3 C CH3   2-Propanol O Acetone 500 C  W‫א‬‫א‬‫א‬٥ J٧ ،‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬K‫א‬ - ٩٥ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬EF‫א‬،‫א‬  W‫א‬‫א‬‫א‬‫א‬  (Cyanohydrine )KHCN‫א‬ .١ CH3 O OH CH3 C H - C H + HCN CN CN  Acetaldehyde cyanohydrine CH3  O - OH CN CH3 C CH3 C CH3 + HCN CN Acetone cyanohydrine  W‫א‬‫ א‬.٢ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  WG-NH2 O    NH Ar  OH  H = G   NH C NH2 ‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬ ‫א‬‫א‬K‫א‬‫א‬‫א‬ F ‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬E‫א‬ O NHNH 2 + CH 3 H C N NH CH3 C CH 3 + CH 3  Acetone Phenylhydrazene - ٩٦ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  WReduction‫א‬‫ א‬.٣ ‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬   KNaBH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ OH O H2/Pt CH3 CH CH3 CH3 C CH3 1)NaBH 4 2)H 2O CH3 CH CH3 OH   2-Propanol  WOxidation‫ א‬.٤ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬ O O ( O ) R C OH  R C H           - ٩٧ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F  W‫א‬‫א‬ .١ O O Cl (2   CH3CH2C H (1  OO C H (4  (CH3)2CHCCH(CH 3)2 (3   O   CH3CH2CH2CCH3 (5   W‫א‬‫א‬‫א‬‫ א‬.٢   Acetophenone (2 Benzaldehyde (1 Benzylphenyl ketone (4 Benzophenone (3 Butanal 3-Pentanone (6 (5  W‫א‬‫א‬ .٣  O Cl +? O H C 1) NaBH 4 C (1 +  ? (2 O 2) H3O ? (3 CH 3 CH 2 CH 2 C  O 1) NaBH 4 +  2) H3O O NH 2 OH  CH 3 C CH 3 Oxidation. ? (4 ? (5 O H 2 / Pt ? (6  CH 3 C H O  CH 3 CH 2 C H - ٩٨ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F  WE1F‫א‬‫א‬ . 2-Chlorocyclohexanone (2   . Propanol (1   . Methyl propyl ketone (3  WE2F‫א‬‫א‬‫א‬ O (4 CHO    CH3 CH2 CH2 C-H (1  O  CH3 CH2 CH2 C-CH3 (6  WE3F‫א‬‫א‬‫א‬ N-OH (4   CH3 CH2 CH2 CH2 OH (2    CH3 -C- CH3 OH (6   CH3 CH2 C CH3  - ٩٩ -



 ‫א‬‫א‬ ‫א‬‫א‬  ‫א‬‫א‬ ٨

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬‫א‬‫א‬   W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬‫א‬ .١  K‫א‬‫א‬‫א‬‫א‬ .٢   W‫א‬‫א‬‫א‬  K٪80‫א‬‫א‬‫א‬   W‫א‬‫א‬  K   W‫א‬‫א‬  Overhead Projector. .١  K .٢  W‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬   - ١٠٠ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W١ J٨ E JCOOH) ‫א‬ ‫א‬‫א‬  KE-OHF ‫א‬EC=OF‫א‬‫א‬K ،‫א‬ ‫א‬‫א‬  K‫א‬‫א‬  W‫א‬‫א‬٢ J٨  W‫א‬‫א‬ J ‫א‬ ‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬   KE8 J1FKW‫א‬‫א‬‫א‬‫א‬K  WE‫א‬‫א‬‫א‬E8 J1FF  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬،Formic HCOOH  Formic acid  K‫א‬  ‫א‬ Acetum  CH3COOH  Acetic acid ‫א‬،‫א‬‫א‬ ‫א‬‫א‬   K‫א‬  ‫א‬ ،Butyrum CH3(CH2)2COOH Butyric acid K‫א‬‫א‬‫א‬  K‫א‬  β،α‫א‬‫א‬، ‫א‬‫א‬  ‫א‬‫א‬α‫א‬‫א‬‫א‬‫א‬KKKγ،  K‫א‬‫א‬‫א‬‫א‬‫א‬   - ١٠١ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬‫א‬ α γ βα O ‫א‬‫א‬ C C C C C C OH 5 4 32 1   W CH3 CH3 CH3 CH CH COOH  2,3-Dimethylbutanoic acid     α،β -Dimethylbutyric acid  WIUPAC ‫א‬‫א‬W ‫א‬‫א‬‫א‬e‫א‬oic acid ‫א‬  ‫א‬‫א‬‫א‬K ‫א‬‫א‬‫א‬ ،‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬ O Br CH3 C OH CH3 CH COOH Ethanoic acid 2-Bromopropanoic acid (Acetic acid) COOH CH3 Cyclohexane CH3 C CHCOOH Carboxylic acid 3-Methyl-2-butenoic acid  WW  W‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.١ - ١٠٢ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ COOH OH CH3 COOH   Benzoic acid   Salicylic acid COOH  P-Toluic acid  K ‫א‬‫א‬ .٢  W COOH COOH COOH COOH COOH COOH CH2 CH2 (CH2)4 COOH COOH CH2 COOH COOH  Oxalic acid  Malonic acid  Succinic acid Adipic acid  Phthalic acid ‫א‬،Fatty acids‫א‬‫א‬ .٣ ‫א‬،2612‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬   CH3 (CH2)14 COOH CH3 (CH2)16 COOH Palmitic acid Stearic acid - ١٠٣ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬‫א‬‫א‬٣ J٨ ،‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬،‫א‬  W‫א‬‫א‬،‫א‬  KO 00،L46Z‫א‬‫ א‬HCOOH Formic acid  KO78،L46Z‫א‬‫ א‬C2H5OH Ethanol ‫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 _+ O OH RC +_ CR  O H O  E‫א‬‫א‬‫א‬F  W‫א‬‫א‬٤ J٨ ‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬   HCl H2O +_ H3O + Cl ‫א‬، ‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬ _+   RCOOH + H2O RCOO + H3O ‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬K‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬ - ١٠٤ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ _ O O R C_ O RC O RC _  O O  W‫א‬‫א‬‫א‬‫א‬‫א‬  WElectron-withdrawing group‫א‬‫ א‬.١ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬‫א‬K‫א‬‫א‬  W‫א‬   ....., -COOH , -SO3H , -CN , -NO2 , Br , Cl ,F Benzoic acid p-Nitro Benzoic acid‫א‬  KPara‫א‬‫א‬-NO2   :Electron-donating group‫א‬‫ א‬.٢ ،‫א‬‫א‬‫א‬‫א‬‫א‬  ،‫א‬‫א‬‫א‬ W -OH , -NH2 , -OCH3 , -CH3 ‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬ JCH3‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬EInductetive effectF ‫א‬EpKaF‫א‬ ‫א‬‫א‬  WEChlorobutyricF Cl Cl Cl CH3CH2CH2COOH CH3CH2CHCOOH CH3CHCH 2COOH CH2CH2CH2COOH  PKa = 4.52  PKa = 4.82  PKa = 2.85  PKa = 4.05 - ١٠٥ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ Z1  W92  W6   W2  ‫א‬  ‫א‬Ka‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬ pKa _+  [ RCOO ] [ H ] Ka = [ RCOOH ] _ log Ka = pKa  K‫א‬pKaKa‫א‬ ‫ ﺗﺰداد اﻟﺤﻤﻮﺿﺔ‬Ka ‫زﻳﺎدة‬   ‫ ﺗﻘﻞ اﻟﺤﻤﻮﺿﺔ‬pKa ‫زﻳﺎدة‬  W‫א‬‫א‬‫א‬‫א‬  ‫ א‬ pKa  Ka  ‫א‬  Ð Ð  3.74 Ð 1.77*10-4 HCOOH  Ð Ð 4.47 Ð 1.76*10-5 CH3COOH  Ð Ð 4.85 Ð 1.43*10-5 CH3CH2COOH  W‫א‬‫א‬٥ J٨ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬،‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬ .١ O   RCH2 OH OR R C H H2Cr2O7 RCOOH + +3 ( ‫) أﺧﻀ ﺮ اﻟﻠ ﻮن‬ Cr  W‫א‬ .٢ ‫א‬‫א‬(Ar)R-CNK‫א‬‫א‬   K‫א‬‫א‬‫א‬ - ١٠٦ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ _ R-X CN    RCN  K‫א‬‫א‬‫א‬   RCN + , + H3O RCOOH + NH4  W‫א‬ .٣  R COOH KMnO4 , C2H5 KMnO4 ,  Ethyl benzene Benzoic acid  W‫א‬‫א‬٦ J٨ ‫א‬ K‫א‬‫א‬‫א‬  K‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫ א‬.١ CH3COOH + NaOH _+ CH3COO Na + H2O   Acetic acid Sodium acetate Ph COOH + NaOH _+ Ph COO Na + H2O   Benzoic acid Sodium benzoate ،‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ - ١٠٧ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ _+ (Ar) R COO Na + H 2O + CO2   (Ar) R COOH + NaHCO 3  K‫א‬،‫א‬‫א‬‫א‬ RCON‫א‬ ‫א‬WRCOOR،‫א‬‫א‬‫א‬RCOCl‫א‬‫א‬‫א‬.٢ O  R-C-O-C-R ‫א‬  W‫א‬‫א‬٧ J٨ E-OHF‫א‬‫א‬‫א‬‫א‬ ‫א‬–NH2Cl-RCOO- JOR‫א‬   ‫א‬ ‫א‬  ‫א‬ ‫א‬  ‫א‬   ‫א‬  ‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬  ‫א‬‫א‬ O ‫א‬ O    CH3 C Cl Acetyl chloride R C X O O  CH3 C OC2H5 Ethyl acetate  R C OR O C NH2 ‫א‬ O O  Benzamide   R C NH2 O ‫א‬ O O CH3 C O C CH3 Acetanhydride RCO CR O _  ‫א‬ O _+  CH3 C O Na+ Sodium acetate R C O M - ١٠٨ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  ‫א‬‫א‬١ J٧ J٨  :Acid halides ‫א‬‫א‬W  ،-yl halide‫א‬‫א‬‫א‬ - ic acid‫א‬  W‫א‬‫א‬ OO CH3 C OH CH3 C Cl Acetic acid Acetyl chloride   :Esters ‫א‬‫א‬W ‫א‬  ‫א‬‫א‬،-ate‫א‬‫א‬‫א‬-ic acid‫א‬  WKE‫א‬‫א‬F‫א‬ ‫א‬‫א‬‫א‬ OO CH3 C OH CH3 C OC2H5   Acetic acid Ethyl acetate  WAmides‫א‬‫א‬W  WKamide‫א‬‫א‬‫א‬ JoicAcid‫א‬ O O CH3 CH2 C OH CH3 CH2 C NH2 Propanoic acid Propanamide   WAcid anhydrides‫א‬‫א‬W‫א‬  .Anhydrideacid‫א‬ - ١٠٩ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ O OO C O OH C OC Benzoic acid Benzoic anhydride   :Acid salts‫א‬W ‫א‬‫א‬  ‫א‬‫א‬،‫א‬‫א‬‫א‬  K‫א‬‫א‬ O O _+ CH3 C OH CH3 C O NH4   Acetic acid Ammonium acetate  W‫א‬‫א‬‫א‬‫א‬‫א‬٢ J٧ J٨ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬ K ‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ O .. _ O O R-C-NH2 , C .. + +  R-C = NH2 R NH2  ‫א‬‫א‬  ‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬ - ١١٠ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬٣ J٧ J٨  K‫א‬ O R C OR SCO1 2 in Benzene OO H2SO4 O ROH O R C OH H+ RC O C R R C OR Acid anhydride Acid Ester NH3 NaOH O O R C OR R C O- N+a   Amide Acid Acid salt    - ١١١ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F O 2)  W‫א‬‫א‬ K١ 1) CH3 CH CH C OH CO2H OH  OH NH2  NH2 O O CH3 CH2 C OCH3 _+  3) CH3 CH2 CH2 C O NH 4  4) OO O CH3 5) C O C CH3 6) HC N CH3   OO  7) CH3 CH2 C Cl  8) CH3 CH2 CH2 C NH2  W‫א‬‫א‬‫א‬‫א‬‫ א‬K٢ a) 2,3-dibromopentanoic acid. b) Methyl benzoate. c) Methyl formamide. d) m-nitrobenzoyl chloride. e) Potassium formate. f) N,N-diethylpropanamide. g) Benzoic formic anhydride. h) Ethyl 2-aminopropanoate.  ‫؟‬‫א‬‫א‬‫א‬ K٣  K‫א‬‫א‬ K  K‫א‬‫א‬ K  K‫א‬‫א‬ K  K‫א‬‫א‬ K  K‫א‬‫א‬ K - ١١٢ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ K٤ + ? ? 1) CN H2O / H ? ?  ? 2) CH3 CH2H5 KMnO 4  O 3) CH3CH2 C OH SOCl 2 Benzene O + H  4) CH3 C OH O 5) 2CH3 C CH3 H2SO4               - ١١٣ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F  WE1F‫א‬‫א‬  WE2F‫א‬‫א‬ 2) 4-Amino-2-hydroxy benzoic acid. 4) Methyl propanoate. 5) Acetic benzoic anhydride. 7) Propanoyl chloride. O (3 CH3-CH2-CH-CH-COOH (1 H-C-NHCH 3 Br Br O_ + (5 OO (7 H-C-O K -C-O-C-H  WE3F‫א‬‫א‬‫א‬  ‫א‬‫א‬‫א‬ K١ ‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬ O + O_   H-C-OH H + H-C-O  ‫א‬‫א‬‫א‬   +  KE H ‫א‬،‫א‬F O + O_ \" ‫\" اﻟﻘﺎﻋﺪة اﻟﻤﺮاﻓﻘﺔ‬ CH3-C-OH  H + CH3-C-O ?‫א‬?E  ‫א‬‫א‬CH3F   KEH+‫א‬F - ١١٤ -

 ‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬‫א‬ ‫א‬ ‫א‬،‫א‬‫א‬ K٢ ‫א‬‫א‬،‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬  WE4F‫א‬‫א‬‫א‬ O HOOC COOH (2 CH3-C-O C2H5 (4  - ١١٥ -



‫א‬  ‫א‬‫א‬ ‫א‬ ٩

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   K‫א‬‫א‬‫א‬   W‫א‬‫א‬  W‫א‬‫א‬‫א‬  K‫א‬ .١  K‫א‬‫א‬‫א‬ .٢  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬.٣   W‫א‬‫א‬‫א‬  K٪90‫א‬‫א‬‫א‬   W‫א‬‫א‬  K   W‫א‬‫א‬  KOverhead Projector  .١ K .٢   W‫א‬‫א‬ K‫א‬‫א‬‫א‬‫א‬ - ١١٦ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W١ J٨ EF‫א‬‫א‬  ‫א‬KEFEF‫א‬ ‫א‬‫א‬KEF‫א‬‫א‬‫א‬‫א‬  K‫א‬RR3N , R2NH , RNH2‫א‬‫א‬ ‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬  ‫א‬  ‫א‬ ‫א‬   ‫א‬ ‫א‬ ‫א‬  ‫א‬E‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬  W‫א‬٢ J٨  W‫א‬١ J٢ J٨  W‫א‬‫א‬‫א‬  3O 2O   1O   ‫א‬ ‫א‬ ‫ א‬‫ א‬ K‫א‬ K‫א‬ K (C2H5)3N (CH3)2NH CH3NH2    Triethylamine  Dimethylamine  Methylamine   N NHCH3 NH2   Pyridine  N-Methyl aniline  Aniline  - ١١٧ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬٢ J٢ J٨  W‫א‬‫א‬W  ‫א‬amine‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ CH3NH2 CH3 CH3 CH3 NH o CH3 N CH3 o o Methylamine (1) Trimethylamine (3) Dimethylamine (2) CH3 CH3 CH3CH2CHNH2 CH3CH2- N - CH3 o Ethyldimethylamine(3ْ) sec-Butylamine (1)  W‫א‬‫א‬‫א‬‫א‬ NH2 NH(CH3) Cl Cl NH2 NO2 Cl O-Nitroaniline 2,4,6-Trichloroaniline N-Methylaniline ‫א‬‫א‬‫א‬‫א‬‫א‬ CH3 NH2 p-Toluidine  KP- Toluidine‫א‬Toluidine‫א‬Aminotoluene ‫א‬،‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ - ١١٨ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ N N N N N H Pyridine H Pyrrolidine H Pyrrole Quinoline Pipyridine  W‫א‬‫א‬W ‫א‬‫א‬‫א‬IUPAC‫א‬‫א‬‫א‬  ‫א‬  ‫א‬       Amino ‫א‬‫א‬،‫א‬‫א‬‫א‬  W‫א‬ CH3 CH3 CH CH2 CH CH3 CH3 CH2 CH CH2 CH CH3 NH2 NH2 5-Methyl -3-aminohexane 2-Amino-4-phenylpentane H2N CH2 CH2 CH2 COOH CH3 CH NH CH2 CH3 4-Aminobutanoic acid CH2CH2CH2CH3 2-(N-Ethyl amino)hexane COOH NH2 P-Aminobenzoic acid  W‫א‬W EAmmoniumFEAmineF ‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬(Anilinium)EAnilineF‫א‬  W‫א‬ - ١١٩ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ CH3 +_ CH3-N-+CH 3 NH3 Br _ I CH3   Tetramethylammonium Anilinium bromide  W‫א‬‫א‬‫א‬٣ J٨ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬   (C2H5)2NH, (CH3)3N, (CH3)2NH, CH3NH2 WEF‫א‬‫א‬ E١١ J٤F‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬E11F  K‫א‬‫א‬‫א‬‫א‬ ،  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬K  ‫א‬‫א‬‫א‬‫א‬E‫א‬‫א‬F‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  KE8-1F‫א‬  K‫א‬‫א‬‫א‬‫א‬‫א‬E8-1F‫א‬ ‫א‬ ‫א‬ ‫א‬‫א‬   ‫א‬   - 42 44 Propane CH3CH2CH2    17 45 Ethylamine CH3CH2NH2   7.5 45 Dimethylamine CH3NHCH3   78 46 Ethyl alcohol CH3CH2OH   100.5 46 Formic acid HCOOH ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬،‫א‬‫א‬K‫א‬‫א‬‫א‬،  K‫א‬ - ١٢٠ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬٤ J٨ ،‫א‬‫א‬‫א‬‫א‬،‫א‬ ‫א‬‫א‬  ‫א‬  K‫א‬‫א‬  RNH2 + HX +_ [ RNH3 ] X  ‫א‬   ‫א‬ ، ‫א‬ ‫א‬    ‫א‬ ‫א‬ π‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬  W‫א‬‫א‬ . NH2 + + + ]  [ NH2 NH2 NH2 _ _ _ Resonance structures of aniline  E‫א‬‫א‬‫א‬F ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬–SO3H‫א‬–NO2‫א‬  ‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬، ‫א‬‫א‬–OCH3‫א‬  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ NH2 NH2 NH2 >> OCH3 NO2   ‫ﺗﻘﻞ اﻟﻘﺎﻋﺪﻳﺔ ﺑﺎﺗﺠﺎﻩ اﻟﺴﻬﻢ‬ - ١٢١ -

 ‫א‬‫א‬  ١٥٣  ‫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‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬Kb R NH2 + H2O +_ R NH3 + OH   Amine Alkylammonium ion Kb = [ R_ N+H3] [ _ ]  OH [ R _ NH2] ‫א‬KK‫א‬Kb  ‫א‬ pKb  Kb‫א‬‫א‬  W‫א‬‫א‬‫א‬pKb  NH2  NH3  CH3NH2  (CH3)2 NH  Kb= _10 K b = 1.8 * _5 _4 _4 4.2 * 10 10  K b= 4.4 * 10  K b= 5.1 * 10   pKb= 9.38  pKb= 4.74  pKb= 3.36  pKb= 3.29     (CH3)3 N      pKb= 4.26     Kb = 5.5 * 10_10   - ١٢٢ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬٥ J٨  W‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬W   W‫א‬‫א‬  W‫א‬‫א‬  J H3N + R X + _   Alkyl halide R NH3 X OH R NH2 + H2O + X o Primaryamine 1  W‫א‬‫א‬‫א‬  J CH3CH2NH2 1) CH3Cl CH3CH2NH 2) OH CH3 ‫أﻣﻴﻦ أوﻟﻲ‬ ‫أﻣﻴ ﻦ ﺛ ﺎﻧﻮي‬ oo   (1) (2)  ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬‫א‬‫א‬– ‫א‬‫א‬K‫א‬‫א‬‫א‬‫א‬‫ א‬K LIAIH4‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬ CH3 NO2 H2 / Pt CH3 NH2 Nitromethane Methylamine NO2 Fe / HCl +_ Na2CO3 NH2 NH3Cl  K‫א‬‫א‬‫א‬‫א‬‫א‬‫ א‬K ‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬LIAIH4‫א‬  K‫א‬ - ١٢٣ -