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Húa Hc Hu C TS Phan Thanh Sn Nam B mụn K Thut Hu C Khoa K Thut Húa Hc Trng i Hc Bỏch Khoa TP HCM in thoi: 8647256 ext 5681 Email: ptsnam@hcmut.edu.vn http://hhud.tvu.edu.vn Ti liu tham kho [1] Paula Y Bruice, Organic chemistry, fifth edition, Pearson Prentice Hall, 2007 [2] Graham T.W Solomons, Craig B Fryhle, Organic chemistry, eighth edition, John Wiley & Sons, 2004 [3] Francis A Carey, Organic chemistry, fifth edition, McGrawHill, 2003 [4] Robert T Morrison, Robert N Boyd, Oragnic chemistry, sixth edition, Prentice Hall, 1992 [5] Trn Th Vit Hoa, Phan Thanh Sn Nam, Húa hu c, NXB i Hc Quc Gia HCM, 2007 [6] Trn Th Vit Hoa, Trn Vn Thnh, Bi hoỏ hu c, NXB i Hc Quc Gia HCM, 2004 [8] Thỏi Doón Tnh, C s lý thuyt hoỏ hu c, NXB Khoa Hc K Thut, 2000 [9] Trn Quc Sn, C s lý thuyt húa hu c, NXB Giỏo Dc, 1979 http://hhud.tvu.edu.vn NI DUNG CHNH ng phõn ca hp cht hu c Hiu ng hp cht hu c C ch cỏc phn ng ca hp cht hu c Alkane Alkene Alkyne Alkadiene Hp cht hydrocarbon thm Dn xut halogen Alcohol Phenol Aldehyde Ketone Carboxylic acid Amine Hp cht diazonium http://hhud.tvu.edu.vn Chng 1: NG PHN ng phõn: nhng hp cht hu c cú cụng thc phõn t ging nhau, cụng thc cu to khỏc ặ tớnh cht húa hc, vt lý, sinh hc khỏc Phõn loi: + ng phõn cu to (phng) + ng phõn lp th: ng phõn hỡnh hc (cis, trans), ng phõn quay (cu dng), ng phõn quang hc http://hhud.tvu.edu.vn I ng phõn cu to Do cú s sp xp khỏc ca cỏc nguyờn t mch C I.1 ng phõn mch C n-butane iso-butane C6H12 methyl cyclopentane cyclohexane http://hhud.tvu.edu.vn I.2 ng phõn v trớ cỏc liờn kt bi, nhúm chc butene-1 C4H8 OH butene-2 OH OH OH OH 1,2- 1,3- OH 1,4- dihydroxy benzene http://hhud.tvu.edu.vn I.3 ng phõn cú nhúm nh chc khỏc dimethyl ketone C3H6O propan-2-one O acetone CHO propionaldehyde propanal propionic aldehyde C3H6O2 COOH Propionic acid O O http://hhud.tvu.edu.vn methyl acetate I.4 ng phõn cú nhúm th khỏc liờn kt vi nhúm nh chc C4H10O diethyl ether O O methyl propyl ether http://hhud.tvu.edu.vn II ng phõn lp th II.1 ng phõn hỡnh hc II.1.1 iu kin xut hin ng phõn hỡnh hc Xut hin phõn t cú b phn cng nhc ặ cn tr s quay t ca cỏc nguyờn t ú nguyờn t liờn kt vi cựng nguyờn t ca b phn cng nhc phi khỏc http://hhud.tvu.edu.vn Thng xut hin cỏc hp cht cú cha: C=C, C=N, N=N, h liờn hp, vũng phng hay cnh abC=Ccd: a b, c d Cl H Cl H http://hhud.tvu.edu.vn 10 V.4 Phn ng vi HNO2 Thc t: NaNO2 + HCl hay H2SO4 a Phn ng ca amine bc Amine thm bc s cho mui diazonium NH2 N+ + NaNO2 + HCl 0-5 oC N Cl+ NaCl + 2H2O Amine bộo bc ặ mui diazonium khụng bn ặ phõn hy thnh alcohol R CH2NH2 + NaNO2 + HCl 0-5 oC http://hhud.tvu.edu.vn R-OH + N2 + H2 O 22 b Phn ng ca amine bc C amine bộo & amine thm u cho Nnitrosoamines CH3 N N O NHCH3 + NaNO2 + HCl 0-5 oC + NaCl + H2O N-nitroso-N-methylaniline R NHCH3 + NaNO2 + HCl 0-5 oC CH3 R N N O http://hhud.tvu.edu.vn + NaCl + H2O 23 c Phn ng ca amine bc Amine bộo bc khụng tham gia phn ng Amine thm bc s cho phn ng th ỏi in t N(CH3)2 + NaNO2 + HCl N(CH3)2 0-5 oC + NaCl + H2O N O p-nitroso-N,N-dimethylaniline http://hhud.tvu.edu.vn 24 VI Mui diazonium VI.1 iu ch mui diazonium HN N O NH2 + + N O chaọm chuyeồn vũ -H+ N N OH H+ N+ N + N N O H H H2O N+ N Cl Clhttp://hhud.tvu.edu.vn 25 VI.2 Phn ng th nhúm diazonium Phn ng th ỏi nhõn n phõn t, tỏch N2 C6H5-N+NCl- + y- ặ C6H5-y + N2 + ClC ch tng t SN1 thụng thng, giai on chm to carbocation C6H5+ a Phn ng vi H2O N+ N Cl OH + H2O H+ o 40-50 C http://hhud.tvu.edu.vn + N2 + HCl 26 b Phn ng vi alcohol Cú phn ng cnh tranh Phn ng th N+ N Cl OC2H5 + C2H5-OH + N2 + HCl Phn ng kh Xy cú mt alcohol khan, H3PO2, hay NaBH4 N+ N Cl + C2H5-OH khan + http://hhud.tvu.edu.vn CH3CHO + N2 + HCl 27 Phn ng kh cng tt nhõn thm cú cha nhúm th hỳt in t o-, p Alcohol mch cng di, cng u tiờn phn ng kh CH3OH ặ 90% SN1 CH3CH2OH ặ 60% SN1 CH3CH2CH2OH ặ 30% SN1 http://hhud.tvu.edu.vn 28 S dng cho cỏc trng hp khụng th tng hp bng ng trc tip CH3 CH3 CH3 NO2 HNO3 H2SO4 + l r NO2 Fe/HCl CH3 CH3 NaNO2 /HCl Br2/CS2 0-5 oC Br NH2 NH2 CH3 CH3 H3PO2 Br N2+Cl- http://hhud.tvu.edu.vn Br 29 c Phn ng vi KI C6H5-N2+Cl- + KI ặ C6H5-I + N2 + KCl Mun thu c dn xut ca Br, Cl ặ cn xỳc tỏc CuCl, CuBr (Sandmeyer), c ch gc t N+ N Cl Cl CuCl + http://hhud.tvu.edu.vn N2 30 NH2 CH3 NaNO2 / HCl N2+ClCH3 H2O 0-5 oC Cl 15-60 oC N2+HSO4- NH2 Cl NaNO2 / H2SO4 NH2 CH3COOH 30 oC CuCl + N2 HSO4 - 40-100 oC N2+Br- NH2 NaNO2 / HBr Cl H2O 0-10 oC CH3 CuCl Cl Br CuBr Cl http://hhud.tvu.edu.vn 100 oC Cl 31 Ar N N BF4- to Ar F + N2+BF4- NH2 HNO2 2.HBF4 CH3 NH2 N2 NaNO2 / HCl H2O CCH2CH3 O 2.HBF4 + BF3 F to CH3 CH3 N2+BF4- F to CCH2CH3 O http://hhud.tvu.edu.vn CCH2CH3 O 32 d Phn ng nitrile húa N+ N Cl C N + KCN to + KCl + N2 H+, H2O COOH http://hhud.tvu.edu.vn 33 Cú th nitrile húa bng CuCN NO2 NH2 N2+ Cl- HNO3 Fe NaNO2 H2SO4 HCl HCl CH3 CH3 CN CuCN CH3 CH3 COOH H2O H+ CH3 CH3 http://hhud.tvu.edu.vn 34 VI.2 Phn ng ghộp ụi diazonium Hp cht diazonium + arene cú nhúm tng hot ặ phm mu azo N2+ Cl- OH oC + N N pH = 8-9 OH p-(phenylazo)phenol N2+ Cl- N(CH3)2 + oC N N pH = 5-7 http://hhud.tvu.edu.vn N(CH3)2 35 N,N-dimethyl-p-(phenylazo)aniline Hp cht diazonium cha nhúm th hỳt in t cng mnh thỡ phn ng ghộp ụi xy cng d N2+ O2N N2+ NO2 NO2 > NO2 N2+ > NO2 http://hhud.tvu.edu.vn N2+ > NO2 36 [...]... phân cực: chỉ dao động trong 1 mặt phẳng nhất định Æ mặt phẳng phân cực •ASTN qua lăng kính Nicol sẽ trở thành ASPC http://hhud.tvu.edu.vn 35 II.3.2 chất hoạt động quang học • ASPC đi qua 1 số hợp chất hữu cơ làm mặt phẳng phân cực quay 1 góc Æ chất hoạt động quang học • Góc quay được xác định bằng phân cực kế http://hhud.tvu.edu.vn 36 ... CH3 http://hhud.tvu.edu.vnH 27 http://hhud.tvu.edu.vn 28 II.2.3 Cấu dạng của hợp chất vòng no •Vòng no 3,4 cạnh không có đồng phân cấu dạng • Sức căng bayer: do sự khác biệt của góc liên kết so với góc hóa trị bình thường (109o28’) α = ½ (109o28’ – góc liên kết của vòng) http://hhud.tvu.edu.vn 29 a Cyclohexane • Các C không cùng nằm trong 1 mặt phẳng để bảo đảm góc liên kêt ~ 109o28’ • Các nhóm thế có

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