acid carboxylic và dẫn xuất

ACID CARBOXYLIC BÉO VÀ DẪN CHẤT 1.Gọi tên CH3 (CH2)2 COOH HOOC CH2 COOH HOOC (CH2)3 COOH HOOC (CH2)2 COOH HOOC CH CH COOH (CH3)2C CH CH2 COOH Acid butyric butanoic Acid succinic butandioic ClCH2 CH2 COCl Acid 2-chloropropanoylchlorid Acid β-chloropropionylchlorid Acid malonic propandioic Acid butendioic (CH3)2CH COOC2H5 Ethylisobutyrat ethylisobutanoat O (CH3)2CH C N Isopropylcyanid Isobutyronitril isobutanonitril O O Anhydrid phthalic Acid glutaric 1,5-pentandioic 4-methyl-3-pentenoic CH3 CH2 CO N(CH3)2 N,N-dimethylpropionamid N,N-dimethylpropanamid O O O Anhydridsuccinic Cl Diclofenac NH Cl CH2 COOH Acid 2-[2’(2”,6”-dichlorophenylamino)]phenylacetic C CH2CH2COOH O Fenbuten 4-oxo-4-p-biphenylbutanoic C3H7 C CH2CH2COOH Bufexamac O 4(4’-propylphenyl)-4-oxo-butanoic Cl C CH2CH2COOH Acid butoxic O 4(3’-chloro-4’-cyclohexylphenyl)-4-oxo-butanoic (CH3)2CHCH2 CH COOH CH3 Ibuprofen Acid 2-methyl-2-(4’-isobutylphenyl)acetic CH COOH C CH O Acid 2-methyl-2-(3’-benzoylphenyl) acetic Ketoprofen Viết công thức hợp chất CH C CH2 CH COOH CH C N O Br acetylbromid acid propenoic CH2 CH C N Acrylonitril CH3CH2C O (CH3)2CH C C NHBr O Cl N-bromopropionamid (CH3)2CH CH COOH NH2 Acid -aminoisovaleric C O N O C 2H N-methyl-N-ethylacetamid isobutyrylclorid O CH (CH3CH2CO)2O Anhydrid propionic (CF3CO)2O Br Anhydrid trifluoroacetic N-bromosuccinimid HS CH2 CH COOH NH2 Acid -amino--thiolpropionic HO CH CH COOH (CH3)2CH CH2 COOH NH Acid -amino--(p-hydroxyphenyl)propionic CH COOH H OH H OH CH C CH COOH CH COOH Acid ,-dimethylbutyric Acid mesotartric CH COOH HO C COOH CH COOH Acid citric Acid isovaleric CH2 CH2 CH CH2 CH COOH NH2 OH NH2 Acid ,-diamino--hydroxycaproic CH3 CH COOH OH Acid lactic Điều chế acid từ alcol carbon (hay hơn) ester malonic pp khác: a Acid valeric CH3 CH CH2 CH2 OH PCl5 CH 3CH2CH2CH2Cl KCN CH3(CH2)3COOH + H2O/H CH 3CH2CH2CH2CN Hoaëc: CH3CH2CH2OH CH2 COOC2H5 COOC2H5 PCl5 C2H5O CH3CH2CH2Cl CH COOC2H5 COOC2H5 CH3CH2CH2CH(COOC2H 5)2 + H2O/H CH 3CH 2CH 2CH(COOH)2 CO2 t o CH3CH2CH2CH2COOH Acid valeric b Tương tự với acid isovaleric (CH3)2CH CH2 OH PCl5 (CH3)2CH CH2 COOH KCN + H2O/H (CH3)2CH CH2 COOH Hoaëc: (CH 3)2CH OH PCl5 CH2 COOC2H5 COOC2H5 + H2O/H t o CO2 C2H5O (CH 3)2CHCH 2COOH c.Acid -methylbutyric CH3 CH2 CH OH CH3 PCl5 CH3 CH2 CH Cl CH3 KCN CH3 CH2 CH CN + CH3 H2O/H CH3CH2CHCOOH CH Acid -methylbutyric d CH3OH I2 / P CH3I CH3 CH CH2 OH PCl5 (CH3)2CH CH2 Cl CH3 CH COOC2H C2H5O COOC2H C2H5O CH COOC2H COOC2H (CH3)2CH CH2 Cl (CH 3)2CHCH 2C(COOC2H 5) CH3I (CH 3)2CHCH 2CH(COOC2H 5)2 (CH 3)2CHCH 2C(COOC2H 5)2 CH + H2O/H (CH 3)2CHCH 2C(COOH)2 CH t o CO2 (CH 3)2CHCH 2CHCOOH CH Acid 2,4-dimethylpentanoic e CH3 CH CH OH PCl5 (CH3)3C Cl CH3 CH2 COOC2H5 COOC2H5 C2H5O CH COOC2H5 COOC2H5 (CH3)3C Cl (CH3)3CCH(COOC2H5)2 + H2O/H (CH3)3CCH2COOH t o CO2 (CH3)3CCH(COOH)2 Acid ,-dimethylbutyric 10 Từ benzen điều chế 24 Từ p-acetylbenzen đ/c COCH Cl2 / s COCH3 COCH COCH [O] NaOH dd CHClCH CHOHCH COCH diacetylbenzen CH2CH3 COONa COOH + I2 + NaOH H2O/H CH2CH CH2CH Acid p-ethylbenzoic 25 Thực p/ứ a OH ONa OH CO2 NaOH dd OH COONa + H t ,p o COOH CH COCl OCOCH3 COOH pyridin Acid acetylsalicylic (aspirin) b CHO CH(OC2H5)2 + C2H5OH CH3 hoaëc CH(OC2H5)2 KMnO4/H H2O COOH CH3 CHO CHO COOH CHO + H2O/H Cl2/aù s CH CHO CCl3 COOH p-carboxylbenzaldehyd 26 Từ p-toluidin ñ/c H2N CH3 (CH3CO)2O CH 3CONH + KMnO4/H CH CH3CONH COOH + C2H5OH/H H2N COOC2H5 H2O CH3CONH COOC2H5 anesthesin H 2N CH3 HOCH2CH2N(C2H5)2 (CH3CO)2O CH3CONH CH3CONH CH3 + KMnO4/H CH3CONH COOH COOCH2CH2N(C2H 5)2 H2O H 2N COOCH 2CH2N(C2H5)2 Novocain 27 Giải thích aspirin thủy phân nhanh gấp 4-8 lần este thông thường O O C CH3 O HO O C CH3 C O C O O O OH C O O Cấu trúc anhydrid Anhydrid thủy phân nhanh este 28 Hoàn thành chuyển hóa a CH3 Br CH Mg ether khan MgBr CH CO2 COOMgBr CH HCl COOH [O] O C C O O NH NH3 C C O O COOH COOH 29 b CH3 CH3 ñp para CH3 NaOH SO3H H2SO4 CH ñp ortho SO 3H CH3 H2O/H+ NaCN SO3Na [O] CH3 CN COOH SO 3H CH3 C2H5OH COOH NaOH NaOH 300OC COOC2H5 COOH ONa CH3COCl COOH OCOCH 30 c COOH + Br R HS COOH HO S BrMgO R N R N (CH2)2 CH2MgBr H2SO4 H2O CH2 (CH2)2 N C R O C R S N R S HO H2O C CH2 (CH2)2 N R N R S 31 d CH2Cl CH2MgCl Mg ether khan H2SO4 OH CH CH2C6H5 OMgBr CH CH2C6H5 + C6H5CHO C6H5 CH CH C6H5d H2O/H Br2 C6H5 CH CH C6H5 Br KOH/alcol Br C6H5 C C C6H5 32 e HO C C OH O O O C6H5OH H2O C C O O HO NaOH pH = C COONa O Phenolphtalein Màu hồng f C6H 5COOH PCl5 C6H 5COCl NH3 C6H 5CONH O C6H 5CH 2NH C NHCH 2C6H P2O5 O Cl C Cl C 6H 5C N H2/Ni C6H 5CH 2NH 33 10 Hoàn thành chuỗi phản ứng a HO COOH CH3O CH3I OH CH 3O COOH OCH3 CH3O SOCl2 COCH 2Br Br2 COCl CH3ZnBr OCH3 CH 3O CH3O COCH3 OCH3 COCH 2NH C(CH 3)3 (CH3)3C NH2 OCH OCH NaBH4 OH OH HO CH 3O CH CH NH C(CH 3)3 2H2O/H+ OH CH CH NH C(CH 3)3 OCH terbutalin 34 10 CH3 b CH3 ClSO2OH CH3 COOH (C3H7)2NH SO2Cl KMnO4 SO2 N(C3H7)2 SO2 N C 3H C 3H Probenecid c Cl Cl CH3 NH3 Cl H2N SO2 KMnO4 Cl Cl COOH Cl COOH O NH2 ClSO2OH Cl ClO2S Cl H 2N SO Cl COOH NH CH O COOH Furosemid 35 d CH + HNO3/H O 2N CH3 KMnO4 O 2N COOH SO2Cl O 2N O C NHCH2CH2N(C2H5)2 H2NCH2CH2N(C2H5)2 O 2N O C Cl [H] H 2N O C NHCH2CH2N(C2H5)2 Procainamid 36 10 e NH C CH3 O COOH H2N H3C N C CH3 H OH C N O H3C NH C CH3 O C NH O H 3C N CH N O H2O H 3C Methaqualon 37 10 f O C C O O Cl O C COOH O C Cl ClSO2OH Cl COOH SO2NH2 NH4OH SO2Cl NH4OH O C Cl C NH SO 2NH O 38 ... 4-phenoxy- 3-( pyrolidin-1-yl )-5 -sulfonylaminobenzoic COOH COOH CH 3O CH COCH CH 3O O COOH Acid 2-acetyl-2(3’,4’-dimethoxyphenyl)acetic Acid 3-oxo- 2-( 3’,4’-dimethoxyphenyl)butanoic Acid 1,4-dihydro-4-oxo-quinolin-3-carboxylic... CH2CH2COOH O Fenbuten 4-oxo-4-p-biphenylbutanoic C3H7 C CH2CH2COOH Bufexamac O 4(4’-propylphenyl )-4 -oxo-butanoic Cl C CH2CH2COOH Acid butoxic O 4(3’-chloro-4’-cyclohexylphenyl )-4 -oxo-butanoic (CH3)2CHCH2... (Metrizamid) O 3-( N-methylacetamido )-5 -acetamido-N-(1’-formyl2,3,4,5tetrahydroxy)penthyl-2,4,6-triiodobenzamid 20 Viết công thức O COOH O CH3 O Anhydrid phthalic Cl Acid m-toluic COONH Amoni p-chlorobenzoat