Acid carboxylic beo va dan chat
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1. The document provides the names and chemical structures of various carboxylic acids and related compounds. 2. Steps are given for synthesizing carboxylic acids from alcohols, alkyl halides, nitriles, and other precursors through reactions such as halogenation, nucleophilic substitution, hydrolysis, and oxidation. 3. Specific syntheses are outlined for derivatives of toluene, benzoic acid, p-toluidine, and other aromatic compounds. Reactions include halogenation, nitrile formation, hydrolysis, acetylation, and oxidation.
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Acid carboxylic beo va dan chat
- 1. 1 ACID CARBOXYLIC BEÙO VAØ DAÃN CHAÁT
- 2. 2 1.Goïi teân CH3 (CH2)2 COOH CH2 COOHHOOC HOOC (CH2)3 COOH Acid butyric butanoic Acid malonic propandioic Acid glutaric 1,5-pentandioic (CH2)2HOOC COOH COOHHOOC CHCH CH2(CH3)2C CH COOH CH2ClCH2 COCl (CH3)2CH COOC2H5 CH3 CH2 CO N(CH3)2 (CH3)2CH C N O O O O O O Acid succinic butandioic Acid butendioic 4-methyl-3-pentenoic Acid 2-chloropropanoylchlorid Acid β-chloropropionylchlorid Ethylisobutyrat ethylisobutanoat N,N-dimethylpropionamid N,N-dimethylpropanamid Isopropylcyanid Isobutyronitril isobutanonitril Anhydrid phthalic Anhydridsuccinic
- 3. 3 COOH NH CH2 Cl Cl C O CH2CH2COOH C3H7 C O CH2CH2COOH Acid 2-[2’(2”,6”-dichlorophenylamino)]phenylacetic Diclofenac 4-oxo-4-p-biphenylbutanoic Fenbuten 4(4’-propylphenyl)-4-oxo-butanoic Bufexamac
- 4. 4 (CH3)2CHCH2 CH CH3 COOH Acid 2-methyl-2-(4’-isobutylphenyl)acetic Acid 2-methyl-2-(3’-benzoylphenyl) acetic C O CH CH3 COOH Ibuprofen Ketoprofen Cl C O CH2CH2COOH 4(3’-chloro-4’-cyclohexylphenyl)-4-oxo-butanoic Acid butoxic
- 5. 5 2. Vieát coâng thöùc caùc hôïp chaát CH2 CH COOH CH3 O Br C CH3 C O N CH3 C2H5 CH2 CH C N acid propenoic acetylbromid N-methyl-N-ethylacetamid Acrylonitril C(CH3)2CH O Cl (CH3CH2CO)2O CH3CH2C O NHBr O O C N C Br isobutyrylclorid Anhydrid propionic N-bromopropionamid N-bromosuccinimid (CF3CO)2O CH COOH(CH3)2CH NH2 CH2 CH COOHHS NH2 Anhydrid trifluoroacetic Acid -aminoisovaleric Acid -amino--thiolpropionic
- 6. 6 CH2CH3 C CH3 CH3 COOH COOH COOH H H OH OH CH2CH2 NH2 CH CH2 CH NH2 COOH OH Acid ,-dimethylbutyric Acid mesotartric Acid ,-diamino--hydroxycaproic CH2 CHO COOH CH2 COOH COOH CH3 COOHCH OH Acid citric Acid lactic CH2HO CH COOH NH2 CH2 COOH(CH3)2CH Acid -amino--(p-hydroxyphenyl)propionic Acid isovaleric
- 7. 7 3. Ñieàu cheá caùc acid töø alcol 4 carbon (hay ít hôn) vaø ester malonic hoaëc pp khaùc: CH2CH3 CH2 OHCH2 PCl5 CH3CH2CH2CH2Cl KCN CH3CH2CH2CH2CN H2O/H + CH3(CH2)3COOH CH3CH2CH2OH CH3CH2CH2Cl PCl5 CH2 CH COOC2H5 COOC2H5 C2H5O COOC2H5 COOC2H5 CH3CH2CH2CH(COOC2H5)2 H2O/H + CH3CH2CH2CH(COOH)2 t o CH3CH2CH2CH2COOH CO2 a. Acid valeric Acid valeric Hoaëc:
- 8. 8 b. Töông töï vôùi acid isovaleric CH2 COOH(CH3)2CH (CH3)2CH OHCH2 KCN H2O/H + PCl5 CH2 COOH(CH3)2CH (CH3)2CH OH H2O/H + PCl5 C2H5O t oCH2 COOC2H5 COOC2H5 CO2 (CH3)2CHCH2COOH c.Acid -methylbutyric CH3 CH3 CH2 H2O/H + PCl5CH3 CH2 CH OH CH CN CH3 KCNCl CH3 CH2 CH CH3 CH3CH2CHCOOH CH3 Hoaëc: Acid -methylbutyric
- 9. 9 d. CH3OH I2 / P CH3I (CH3)2CH CH3 PCl5 CH ClCH3 CH2 OH CH2 C2H5O CH COOC2H5 COOC2H5 CH2 COOC2H5 COOC2H5 (CH3)2CH ClCH2 (CH3)2CHCH2CH(COOC2H5)2 CH3 CH3IC2H5O (CH3)2CHCH2C(COOC2H5) (CH3)2CHCH2C(COOC2H5)2 H2O/H + CH3CH3 t o CO2 (CH3)2CHCH2C(COOH)2 (CH3)2CHCH2CHCOOH Acid 2,4-dimethylpentanoic
- 10. 10 OH PCl5 CH3 CH3 CH CH3 (CH3)3C Cl CH COOC2H5 COOC2H5 CH2 COOC2H5 COOC2H5 C2H5O (CH3)3C Cl (CH3)3CCH(COOC2H5)2 H2O/H + (CH3)3CCH(COOH)2(CH3)3CCH2COOH t o CO2 e. Acid ,-dimethylbutyric
- 11. 11 4. Ñieàu cheá acid acrylic töø etylen COOHKCNCH2 CH2 Cl2 200 600O C CH2 CH2CHCH CH2 CHCl CN H2O/H + CH2 CH2 HBr CH3CH2Br Mg/ete khan CH3CH2MgBr CO2 CH3CH2COOMgBr H2O/H + CH3CH2COOH Br2/P CH3CHBrCOOH KOH/alcol COOHCH2 CH hoaëc:
- 12. 12
- 13. 13
- 14. 14 7. Hoaøn thaønh chuoãi p/öù: C3H7COOH Ca(OH)2 C3H7 C3H7C O (C3H7COO)2Ca to HCN OH CN C3H7 C3H7 C COOH OHC3H7 C3H7 C H2O/H + a. b. CH2CHCH2 CH2CHCH3 Cl2 to cao Cl HBr Br CH2CH2CH2 Cl CH2 CN H2O/H + CH2 COOHCH2Cl KCN(1 mol) CH2CH2CH2 Cl 2 NaOH dd HOCH2CH2CH2COONa H + HOCH2CH2CH2COOH
- 15. 15 c. (CH3)2CH COOH Br2 / P C CH3 CH3 Br COOH C2H5OH/H2SO4 Br C CH3 CH3 COOC2H5 Cl ONa Cl O C CH3 CH3 COOC2H5 Clofibrate d. COOH CH2OH [H] PCl5 KCN CH2Cl CH2CN CH2CN Br2 CH CNBr C6H6 AlCl3 C6H5 CH CN H2O/H + (C6H5)2CHCOOH NaNH2 CH3I 1. 2. CHCH3 CN CH COOH H2O/H + CH3
- 16. 16 8. Ñieàu cheá acid pantothenic C KCNH3C H CH3 CHO HCHO (CH3)2C CH2OH CHO (CH3)2C CH2OH CHOH CN H2O/H + CH2OH CHOH COOHC CH3 H3C Acid 3,3-dimethyl-2,4-dihydroxybutyric COOHCOOH COOH[H] Cl CH2 CH2CH2 CH2 KCN N C H2N -alanin COOHH3C CH2OH CHOH CH2 CH2C CH2OH CHOH COOHC CH3 H3C COOHCH2 CH2H2N+ CH3 CO NH Acid pantothenic
- 18. 18 1. Goïi teân COOH Cl NH2 COCl Br COONa COOC2H5 NH2 COOH COCH3 Acid 2-cloro-4-aminobenzoic p-bromobenzoylclorid natribenzoat Ethyl p-aminobenzoat p-acetylbenzoic COOH OH COOH COOH HO OH OH COOH Acid o-hydroxybenzoic Acid salicylic Acid phthalic Acid 2,4,6-trihydroxybenzoic Acid gallic NH O O Phthalimid
- 19. 19 COOH O H2NO2S N 1 2 3 6 4 5 Acid 4-phenoxy-3-(pyrolidin-1-yl)-5-sulfonylaminobenzoic 1 2 3 4 CH3O CH3O CH COCH3 COOH Acid 2-acetyl-2(3’,4’-dimethoxyphenyl)acetic Acid 3-oxo-2-(3’,4’-dimethoxyphenyl)butanoic N H COOH O Acid 1,4-dihydro-4-oxo-quinolin-3-carboxylic
- 20. 20 COOH I I I NH CH3NHC O H3C C O Acid 3,5-diacetamido-2,4,6-triiodobenzoic CH3 1 2 3 6 4 5 O I I I NH CH3 NH C O H3C C O N C CH CHO (CHOH)3 CH2OH 3-(N-methylacetamido)-5-acetamido-N-(1’-formyl- 2,3,4,5tetrahydroxy)penthyl-2,4,6-triiodobenzamid (Metrizamid) Acid iotalamid
- 21. 21 2. Vieát coâng thöùc O O O COOH CH3 COOH COOH C N Anhydrid phthalic Acid m-toluic Acid terephthalic Benzonitril Cl COONH4 COOCH2C6H5 H3C CH2CH2COOH C O Br Amoni p-chlorobenzoat benzylbenzoat Acid 3-(p-tolyl)propionic benzoylbromid
- 22. 22 3. Töø toluen ñieàu cheá CH3 KMnO4/H + COOH a. b. c. Cl COOHCH3 Cl2/Fe CH3 KMnO4/H + Cl CH3 Cl2 / aùs CH2Cl KCN CH2CN H2O/H + CH2COOH
- 23. 23 e. f. COOH H2O/H + CH3CH3 Br2/Fe Br Mg/ete khan MgBr CO2 COOMgBr CH3CH3 CH3 COOH Cl2/FeKMnO4/H + Cl CH3 COOH d. CH3CH3 Cl2 / aùs CH2Cl KCN CH2CN H2O/H + CH2COOH Br2/Fe Br Br BrBr 3.
- 24. 24 4. Töø benzen ñieàu cheá
- 25. 25 5. Töø p-acetylbenzen ñ/c Cl2 / aùs COCH3 CH2CH3 I2 NaOH+ COOH H2O/H + CH2CH3 CH2CH3 COONa diacetylbenzen Acid p-ethylbenzoic NaOH dd COCH3 COCH3 COCH3 COCH3CHClCH3 CHOHCH3 [O]
- 26. 26 6. Thöïc hieän p/öù Acid acetylsalicylic (aspirin) CO2NaOH dd OH OHONa t o p, COOH H +COONa OH CH3COCl pyridin OCOCH3 COOH COOH KMnO4/H + CH3 CH3 COOH CHO CH(OC2H5)2 C2H5OH2 CHOCH(OC2H5)2 H2O a. b. hoaëc H2O/H + CHO CH3 CHO CCl3 Cl2/aùs3 COOH CHO p-carboxylbenzaldehyd
- 27. 27 7. Töø p-toluidin ñ/c KMnO4/H + CH3CH3 COOH H2O H2N H2N (CH3CO)2O CH3CONH CH3CONH C2H5OH/H + COOC2H5COOC2H5 CH3CONH anesthesin KMnO4/H + CH3CH3 COOH H2O H2N (CH3CO)2O CH3CONH CH3CONH HOCH2CH2N(C2H5)2 CH3CONH COOCH2CH2N(C2H5)2 COOCH2CH2N(C2H5)2H2N Novocain
- 28. 28 CH3CH3CO C O O HO OHCO O C O O O O O C 8. Giaûi thích aspirin thuûy phaân nhanh gaáp 4-8 laàn caùc este thoâng thöôøng Caáu truùc anhydrid Anhydrid thuûy phaân nhanh hôn este
- 29. 29 9. Hoaøn thaønh caùc chuyeån hoùa CH3 Br Mg ether khan CO2 MgBr CH3 CH3 COOMgBr HCl CH3 COOH [O] COOH COOH NH3NH O CC O OO O C C a.
- 30. 30 b. CH3 H2SO4 ñp para ñp ortho CH3 CH3 CH3 COOH NaOH NaCN SO3H SO3Na CN CH3 CH3 H2O/H + 2 C2H5OH COOC2H5 [O] COOH COOH CH3 SO3H COOH SO3H NaOH NaOH 300O C ONa CH3COCl OCOCH3 9.
- 31. 31 c. COOHCOOH O H2SO4 Br + HS R S R R HO H2O C S RC S BrMgO CH2 (CH2)2 NN R R (CH2)2 CH2MgBrNN RC S CH2 (CH2)2 NN R H2O HO 9.
- 32. 32 CH2Cl C6H5CHO CH2MgCl Mg ether khan CH OMgBr CH2C6H5 H2O/H + CH CH2C6H5 OH H2SO4 C6H5 CH CH C6H5 C6H5 CH Br CH Br C6H5 Br2 KOH/alcol C6H5 C C C6H5 d. d. 9.
- 33. 33 O H2O 2O C O O C C O C OHHO C6H5OH O NaOH C HO COONa pH = 9 e. f. Phenolphtalein Maøu hoàng C6H5COOH PCl5 C6H5COCl NH3 C6H5CONH2 P2O5 C6H5C N H2/Ni C6H5CH2NH2 Cl C O ClC6H5CH2NH NHCH2C6H5C O 9.
- 34. 34 10. Hoaøn thaønh chuoãi phaûn öùng COOHHO OH CH3I2 COOHCH3O OCH3 CH3O OCH3 COCl SOCl2 COCH3 OCH3 CH3O CH3ZnBr OCH3 CH3O COCH2Br (CH3)3C NH2Br2 CH3O OCH3 COCH2NH C(CH3)3 NaBH4 CH3O OCH3 CH CH2 NH C(CH3)3 OH H2O/H + 2 HO OH CH CH2 NH C(CH3)3 OH a. terbutalin
- 35. 35 b. COOHCH3 ClSO2OH SO2Cl CH3 (C3H7)2NH SO2 N(C3H7)2 CH3 KMnO4 SO2 N C3H7 C3H7 COOHCH3 COOH ClSO2OHKMnO4 ClCl ClCl ClCl ClO2S NH3 COOH ClCl H2N SO2 COOH Cl H2N SO2 O NH CH2O NH2 Furosemid Probenecid c. 10.
- 36. 36 d. CH3 HNO3/H + O2N CH3 KMnO4 O2N COOH O2N O C Cl SO2Cl H2NCH2CH2N(C2H5)2 O2N C NHCH2CH2N(C2H5)2 O H2N [H] C NHCH2CH2N(C2H5)2 O Procainamid
- 37. 37 e. O C NH C O CH3 COOH H2N H3C NH H3C NH C O CH3 H3C O C CH3 C OH N H N Methaqualon H3C O CH3 H2O N N 10.