أساسيات الكيمياء العضوية - نظري

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ CH3CH2 C N H2 / Pd or CH3 CH2 CH2 NH2 LiAlH4 / Ether CN H2 / Pd CH2 NH2 ‫א‬‫א‬Hofman degradation‫א‬W NaOBr‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬E‫א‬‫א‬‫א‬F O CH3(CH2)4 C NH2 + Br2 4NaOH CH3(CH2)4 NH2 + By Products H2O ‫א‬‫א‬‫א‬‫א‬، ‫א‬‫א‬  W  K‫א‬‫א‬‫א‬  J١ KNitroalkanes‫א‬‫א‬‫ א‬ J٢ ‫א‬‫א‬‫א‬‫א‬  J٣ ‫א‬Nitrobenzene‫א‬‫א‬‫א‬Phenylamine K‫א‬‫א‬‫א‬‫א‬‫א‬ - ١٢٤ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  W‫א‬٦ J٨  W‫א‬‫א‬  W‫א‬HCl‫א‬‫א‬‫ א‬ J١ CH3 CH2 NH2 + HCl CH3 CH2 N+ H3 _ Cl (CH3)3 N + HCl +_ (CH3)3 NHCl  WNitrous acid‫א‬‫ א‬ J٢ ‫א‬‫א‬–‫א‬‫א‬‫א‬‫א‬  J E٥ J F‫א‬‫א‬ NaNO2 K‫א‬‫א‬‫א‬Diazonium salts‫א‬ ‫א‬‫א‬،‫א‬‫א‬ ‫א‬ K‫א‬‫א‬‫א‬ Ph NH2 + HNO2 O + 0-5 C Ph N2 Diazonium ion   ‫א‬F‫א‬‫א‬‫א‬‫א‬‫א‬  J ‫א‬‫א‬‫א‬‫א‬‫א‬ENaNO2HCl ‫א‬‫א‬ ‫א‬‫א‬‫א‬،‫א‬  KEFNitrosoamine ‫א‬‫א‬‫א‬‫א‬  W‫א‬‫א‬ CH3 (CH 2)4 CH2 NH 2 HNO2 ‫א‬ + N2 o (1) amine - ١٢٥ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ CH3(CH2) NH HNO2 N=O + H2O o CH3 CH2-N-CH2 CH3 + H2O   2 amine  N-Nitrosodiethylamine  (CH3 CH2)3 N HNO2 No reactions.   W‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬  J٣  ‫א‬ J  ‫א‬ J ‫א‬ J  W‫א‬‫א‬ K١ ‫א‬‫א‬‫א‬‫א‬‫א‬  K NH2 NH2 Br2 / H2O Br Br Br Aniline 2,4,6-Tribromoaniline ‫א‬‫א‬‫א‬  K‫א‬‫א‬‫א‬‫א‬، NH2 NHCOCH3 NHCOCH3 NH2 (CH3CO)2O Br2 + H2O / H Aniline Acetanilide Br Br p-Bromoacetanilide p-Bromoaniline  W‫א‬‫א‬ K٢ ‫א‬‫א‬‫א‬‫א‬  ‫א‬‫א‬–N+H3‫א‬‫א‬ p- Nitroaniline ‫א‬‫א‬‫א‬  W‫א‬ - ١٢٦ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ NH2 NHCOCH 3 NHCOCH 3 NH2 (CH3CO)2O O + H2O/H H2SO4/15C H2O NO2 NO2  P-Nitroacetanilide P-Nitroaniline   W‫א‬‫א‬ K٣ –‫א‬‫א‬‫א‬‫א‬‫א‬  K NH2 +_ + NH3HSO4 NH3 H2SO4 O 180-200 C Aniline Anilinium hydrogen _ sulphate SO3 Sulphanilic acid  W‫א‬‫א‬‫א‬٧ J٨ ‫א‬، ، ‫א‬    ‫א‬H2N-(CH2)6-H2N\"1,6-hexamethylenediamine\" hexamethylenediamine  ٢٧٠‫א‬C6H12N4W‫א‬‫א‬‫א‬،urotropin ،EformaldehydeF‫א‬‫א‬Ko  o٩٥‫א‬E٪٢٧F‫א‬E٪٣٠F‫א‬ ‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬،octogen‫א‬hexogen‫א‬  C6H5-NH2 aniline‫א‬‫א‬ ‫א‬‫א‬‫א‬‫א‬K‫א‬ ‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ ، ‫א‬‫א‬،‫א‬‫א‬‫א‬‫א‬‫א‬،‫א‬‫א‬‫א‬ - ١٢٧ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  ،‫א‬‫א‬‫א‬‫א‬‫א‬ ‫א‬‫א‬‫א‬،EhydroquinoneF  KE‫א‬F‫א‬‫א‬‫א‬ ‫א‬‫א‬،‫א‬‫א‬  K،    - ١٢٨ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F  W‫א‬‫א‬‫ א‬K١ 1) CH3 CH2 N(CH3)2 2) CH3 CH2 CH CH3 NH2 3) +_ 4) CH3 CH CH2 CH2CH2 CH3 CH2 N(CH3)3I Br NH2 5) NH2 6) CH CH2 CH2 NH2 OH Br  W‫א‬‫א‬‫ א‬K٢ 1) Cyclopentylamine . 2) B-phenylethylamine . 3) 1,6-Hexamethylendiamine . 4) Benzylamine . 5) N,N-Dimethylamine . 6)tetra-n-Butylammonium iodide . 7) P-Aminobenzoic acid .  K‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٣ 1) CH3 CH2 CH NH2 +_ CH3 2) (CH3)3 NHNO3 4) (CH3CH2) C NH2 3) NH +_ 6) NCH3 5) N(CH3)2 Cl 7) N(CH3)2 8) (CH3)2 CH +N (CH3)3 _ Br  K‫؟‬‫א‬‫א‬‫א‬‫א‬‫א‬‫א‬ K٤  W‫א‬‫א‬ K٥ O2N ,NH2 CH3O ,NH2 NH2 (A    - ١٢٩ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬ , , ,  NH3 O (B  (CH3)2 NH (CH3)3 N  CH3-C-NH2  W‫א‬‫א‬ K٦ a) (CH3CH2)2 NH 1) CH3Cl ? 2) OH  Br Br ? b)  NO2 H2 / Pt NH2  c) CH3CH2CN ? O 4NaOH ? H2O d) CH3CH2 C NH2 + Br2   e) CH3NH2 + ? +_ CH3 NH3Cl  f) (CH3CH2)2 N CH3 HNO2 ? NH2 NH2 Br Br g) + ?  Br h) NH2 + CH3Cl  ?    - ١٣٠ -

 ‫א‬‫א‬  ١٥٣  ‫א‬  ‫א‬  ‫א‬‫א‬ ‫א‬  E‫א‬‫א‬F 1) Ethyl dimethyl amine .  WE1F‫א‬‫א‬ 5) O- bromo aniline . 4) 1-Amino-4-bromo pentane .  WE٢F‫א‬‫א‬ CH2NH2 (4   NH2 (1   +_  (CH3CH2CH2CH2)4 N I (6  WE٣F‫א‬‫א‬  KE3  KE2  KE6  KE4  WE٥F‫א‬‫א‬  P-methoxy aniline > Aniline > P-Nitro aniline .  WE٦F‫א‬‫א‬ CH3CH2CH2 NH2 (c (CH3CH2)2 N CH3 (a HCl (e  K (f   - ١٣١ -

‫א‬‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬  ‫א‬‫א‬  W‫א‬‫א‬‫א‬  ‫א‬W‫א‬،‫א‬‫א‬‫א‬K‫א‬‫א‬، K١   ١٩٨٩ ١٩٩٠‫א‬W‫א‬،‫א‬‫א‬K،‫א‬،‫ א‬K٢   ١٩٩٦،‫א‬،‫א‬،‫א‬‫א‬K،‫ א‬K٣    ١٩٩٨،‫א‬،‫א‬،‫א‬K‫א‬، K٤  ،‫א‬‫א‬‫א‬K،‫א‬‫א‬،‫א‬،‫ א‬K٥  ٢٠٠٠،‫א‬،‫א‬  W‫א‬‫א‬‫א‬W  1.Fessenden, Ralph J.and Fessenden, Joan S. Organic Chemistry ,2nd ed, PWS, Boston 1982. - ١٣٢ -

‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬  ‫א‬   J٢ J  K K K K K K K K K K K K K K K K K K K K K K K K K W١ J١   J٣ J  K K K K K K K K K K K K K K WFunctional Group‫א‬‫א‬٢ J١   J٥ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J١   J٨ J  K K K K K K K K K K K K K K K K K K K K K K K K K K K    J٩ J  K K K K K K K K K K K K K K K K K K K K K K K ١ J٤‫א‬‫א‬   J١١ J K K K K K K K K K K K K K K K K K K K K K K K K W‫א‬١ J٢   J١١ J K K K K K K K K K K K K K K K K K K K W‫א‬ J   J١١ J K K K K K K K K K K K K K K K K K K K K WAlkanes‫א‬٢ J٢   J١٣ J K K K K K K K K K K K K K K K KWAlkyl Group ER-F‫א‬   J١٤ J K K K K K K K K K K K K K K K WCycloalkanes ‫א‬‫א‬   J١٥ J K K K K K K K K K K K K K K KWIUPAC‫א‬‫א‬‫א‬   J٢٢ J K K K K K K K K K K K K K K K K K K K K KWalkenes‫א‬٣ J٢   J٢٨ J K K K K K K K K K K K K K K K K K KW‫א‬‫א‬W   J٣١ J K K K K K K K K K K K K K K K K K K K K WAlkynes‫א‬٤ J٢   J٣١ J K K K K K K K K K K K K K K K K K K K K W‫א‬١ J٤ J٢   J٣٤ J K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬‫א‬   J٣٨ J K K K K K K K K K K K K K K K K K K K K K K2-5   J٤٠ J K K K K K K K K K K K K K K K K K K K K K K٢ J٥‫א‬   J٤٢ J K K K K K K K K K K K K K K K K K K K K K K K K KW١ J٣   J٤٢ J K K K K K K K K K K K K K K K K K K K K K K W‫א‬٢ J٣   J٤٣ J K K K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬٣ J٣   J٤٤ J K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬٤ J٣   J٤٤ J K K K K K K K K K K K K K K K K K K K KW‫א‬٥ J٣   J٤٨ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٦ J٣

‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬   J٤٨ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٧ J٣   J٥١ J K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٨ J٣   J٥٣ J K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬٩ J٣   J٥٤ J K K K K K K K K K K K K K K K K K K K K K K K    J٥٦ J K K K K K K K K K K K K K K K K K K K K K K ٣ J٨   J٥٨ J K K K K K K K K K K K K K K K K K K K K K K K K K W١ J٤   J٥٨ J K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٢ J٤   J٥٩ J K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٤   J٥٩ J K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٤ J٤   J٦١ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٤   J٦٣ J K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٦ J٤   J٦٤ J K K K K K K K K K K K K K K K K K K K K K K K    J٦٦ J  K K K K K K K K K K K K K K K K K K K K K K ‫א‬   J٦٨ J  K K K K K K K K K K K K K K K K K K K K K K K KW١ J٥   J٦٩ J K K K K K K K K K K K K K K K K K K K K K KW‫א‬٣ J٥   J٧١ J K K K K K K K K K K K K K K K K K K K K K K K KW‫א‬   J٧٢ J K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٤ J٥   J٧٣ J K K K K K K K K K K K K K K K K K K KW‫א‬‫א‬٥ J٥   J٧٥ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٦ J٥   J٧٨ J K K K K K K K K K K K K K K K K K K K K K KE‫א‬‫א‬F   J٨٢ J K K K K K K K K K K K K K K K K K K K K K K K K KW١ J٦   J٨٢ J K K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٢ J٦   J٨٣ J K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬   J٨٤ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٦   J٨٥ J K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٤ J٦

‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬   J٨٦ J  K K K K K K K K K K K K K K K KW‫א‬‫א‬‫א‬W    J٨٦ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٦   J٨٧ J K K K K K K K K K K K K K K K K K K K K K KE‫א‬‫א‬F   J٨٩ J K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J٩١ J K K K K K K K K K K K K K K K K K K K K K K K K K W١ J٧   J٩١ J K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٢ J٧   J٩٣ J K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬‫א‬٣ J٧   J٩٤ J K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٤ J٧   J٩٥ J K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٥ J٧   J٩٨ J K K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J٩٩ J K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J١٠١ J  K K K K K K K K K K K K K K K K K K K K K K K KW١ J٨   J١٠١ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬٢ J٨   J١٠٣ J  K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٣ J٨   J١٠٤ J  K K K K K K K K K K K K K W‫א‬‫א‬‫א‬‫א‬٣ J٨   J١٠٤ J  K K K K K K K K K K K K K K K K K K W‫א‬‫א‬٤ J٨   J١٠٦ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬٥ J٨   J١٠٧ J  K K K K K K K K K K K K K K K K KW‫א‬‫א‬٦ J٨   J١٠٨ J  K K K K K K K K K K K K K K K K KW‫א‬‫א‬٧ J٨   J١٠٩ J  K K K K K K K K K K K K K K‫א‬‫א‬١ J٧ J٨   J١١٢ J  K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J١١٤ J  K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J١١٧ J  K K K K K K K K K K K K K K K K K K K K K K K K W١ J٨   J١١٧ J  K K K K K K K K K K K K K K K K K KW‫א‬٢ J٨   J١٢٠ J  K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬٣ J٨

‫א‬ ١٥٣ ‫א‬ ‫א‬‫א‬ ‫א‬   J١٢١ J  K K K K K K K K K K K K K K K K K K K K KW‫א‬٤ J٨   J١٢٥ J  K K K K K K K K K K K K K K K K K K K K W‫א‬٦ J٨   J١٢٩ J  K K K K K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J١٣١ J  K K K K K K K K K K K K K K K K K E‫א‬‫א‬F   J١٣٢ J  K K K K K K K K K K K K K K K K K K K K K K K K K K‫א‬‫א‬   J١٣٢ J  K K K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬    J١٣٢ J  K K K K K K K K K K K K K K K K K K K K W‫א‬‫א‬‫א‬W 

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