10
M()C L()C Lai n6i dati 3 Chuang 13. HQp chat nitrJ 13.1. H<;1pchat nitrozo 13.1.1. Phuong phap t6ng h<;1p 13.1.2. Tfnh chat 13.2. H<;1pchat nitro 13.2.1. Phuong phap t6ng h<;1p 13.2.2. Tfnh chat 13.3. H<;1pchat isoxyanat ya diisoxyanat 13.3.1 Phuong phap Mng h<;1p 13.3.2. Tfnh chat 1. Tac dvng YClinuClc 2. Tac dvng YCliancol 3. Tac dvng YCliamin 13.4. H<;1pchat azit 13.4.1. Phuong phap t6ng h<;1p 13.4.2. Tinh chat cua azit 1. Phan ling khti azit 2. Phan ling phan huy cae ankylazit 3. Phan ling phan huy cae axylazit 13.5. H<;1pchat diazo 13.5.1. Phuong phap t6ng h<;1p 13.5.2. Tinh chat cua h<;1pchat diazo 1. Tac dvng YCliaxit 2. Tac dvng YClicloruaaxit hay anhidrit axit 3. Tac dvng YClixeton 4. Phan ling phan My h<;1pchat diazo 5. Tac dvug YClian ken 13.6. Amin 13.6.1. Danh phap 13.6.2. Phuong phap t6ng h<;1p 1. Ankyl h6a trl,ic tier amoniac hay amin 2. Phan ling Gabriel (phan ling ankyl h6a gian tier) 3. Phan ling thoai ph an Hofmann 4. Phan ling khti . a) Khti h<;1pchat nitro 16 16 16 17 18 18 24 24 24 25 25 26 26 26 27 27 27 28 29 29 30 30 30 31 31 31 32 32 34 34 35 35 36 36

Cơ sở hoá học hữu cơ : Tập III

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Page 1: Cơ sở hoá học hữu cơ : Tập III

M()C L()C

Lai n6i dati 3

Chuang 13. HQp chat nitrJ

13.1. H<;1pchat nitrozo13.1.1. Phuong phap t6ng h<;1p13.1.2. Tfnh chat

13.2. H<;1pchat nitro13.2.1. Phuong phap t6ng h<;1p13.2.2. Tfnh chat

13.3. H<;1pchat isoxyanat ya diisoxyanat13.3.1 Phuong phap Mng h<;1p13.3.2. Tfnh chat

1. Tac dvng YClinuClc2. Tac dvng YCliancol3. Tac dvng YCliamin

13.4. H<;1pchat azit13.4.1. Phuong phap t6ng h<;1p13.4.2. Tinh chat cua azit

1. Phan ling khti azit2. Phan ling phan huy cae ankylazit3. Phan ling phan huy cae axylazit

13.5. H<;1pchat diazo13.5.1. Phuong phap t6ng h<;1p

13.5.2. Tinh chat cua h<;1pchat diazo1. Tac dvng YCliaxit2. Tac dvng YClicloruaaxit hay anhidrit axit3. Tac dvng YClixeton4. Phan ling phan My h<;1pchat diazo5. Tac dvug YClian ken

13.6. Amin

13.6.1. Danh phap

13.6.2. Phuong phap t6ng h<;1p1. Ankyl h6a trl,ic tier amoniac hay amin2. Phan ling Gabriel (phan ling ankyl h6a gian tier)3. Phan ling thoai ph an Hofmann4. Phan ling khti .

a) Khti h<;1pchat nitro

16161617181824242425252626262727272829293030303131313232343435353636

Page 2: Cơ sở hoá học hữu cơ : Tập III

b) Khit h<;1pch~t mtrinc) Khit oximd) Khit amite) Khit imin

13.6.3. Tfnh chat v~t ly13.6.4. Cau trUc cua amiD

13.6.5. Tfnh chat hoa hQC1. Tfnh bazd

2. S1,1t~o muoi3. Pha.n ungcua hidro cua N- H4. Phan ung t~o thanh isonitrin

5. Tac d\mg voi SOClz6. Halogen hoa amiD

7. Tac d\mg voi SF48. Tac d\lng voi axit nitrd9. Phan ung oxi hoa10. Phan ung the VIlOnhan benzen cua amiD thdm

a) Phan ung halogen hOab) Phan ung nitro hoac) Phan ung axyl hoad) Phan ung Vilsmeiere) Phan ung sunfo hoaf) Phlm ung sunfoclo hoa

11. Phan ung dliic trung xac dinh amiD13.7. H<;1pchat amoni b~c bOn

13.7.1. Phlm ung tach cua h<;1pchat amoni b~c bon13.7.2. Xuc tac chuyen pha

13.8. Muoi diazoni13.8.1. Cau trUc cua cation diazoni

13.8.2. Can b~mg axit - bazd cua ion diazoni13.8.3. Tfnh chat cua muoi diazoni

1. Phlm ung tach Nza) Phan ung t~o thanh phenolb) Phan ung t~o thanh Ar- I

, c) Phan ung t~o thanh thiophenol Ar-SHd) Phan ung t~o thanh Ar-F (phan ung Schiemann)

e) Phan ung t~o thanh Ar- NOz (phan ung Gatterman)f) Phan ung Sandmeyer

g) Phan ung the Nz bang Hh) Phan ung aryl hoa (phan ung Gomberg- Bachmann)

2. Phan ung tier vi azoa) Phanung voi anilinb) Phan ung voi phenol va ddn xuat

13.9. Amin khong no - enamin va azometyl

3738383941

43444449505151525252545656575858596061

6263666768697070707171727273747678788181

Page 3: Cơ sở hoá học hữu cơ : Tập III

13.10. Diamin

13.10.1. PhuC1ng phap t6ng hIJp13.10.2. Tinh chat

13.11. Chat mau

13.11.1. Quan ni~m va cau truc chat mau13.11.2. Chat mau t\j nhien13.11.3. Phalli nhui)m

13.12. T6ng hIJp hfiu cC113.12.1. Cau truc bi) khung ml;tch cacbon

a) Tang mi)t cacbonb) Tang hai cacbonc) Tang ml;tch cacbond) Tang ml;tch cacbon chua n6i bae) Tang ml;tch cacbon chua n6i d6i

13.12.2. Nh6m chuc

a) Dua nh6m chuc vao phan titb) Lol;ti bO nh6mchucc) Chuyen h6a nhOm chuc

13.12.3. Kiem chung ve h6a h<;>cl~p the

a) Phlm ung the SN2b) Hidro hOa xuc tac ankyl

c) Khit bang Na trong NH3d) Oxi h6a anken bang tetroxit osmie) Ci)ng halogen vao ankenf) Tach luang phan titg) Hidro bo h6ah) Epoxy hOa ankeni) Md yang epoxitk) Ci)ng cacben

13.12.4. Nh6m baa v~

13.12.5. L~p sC1do t6ng hIJp

Chuang 14. Hqp chat dj vong

858586888890929696969697979797979798989898989898999999999999

100

14.1. HIJp chat d! yang khOng thC1m14.1.1. Danh phap14.1.2. PhuC1ng phap Mng hIJp14.1.3. Tinh chat cua d! yang khOng thC1m

14.2. HIJp chat d! yang thC1m14.2..1. D! yang Ham Cl;tnh

1. PhuC1ng phap t6ng hIJp2. Tinh chat v~t If3. Cau truc cua furan, pyrol va thiophen4. Tinh chat h6a h<;>c

a) Tinh axit

103103105106107107108109110113113

Page 4: Cơ sở hoá học hữu cơ : Tập III

b) Tinh bazo

c) Phan dng the electrophin SEd) Phan dng khli

e) Phan dng thuy phan0 Phan dng chuyen hoa giUa cac dj tog) Phan dng c(>ng

14.2.2. HCJpchat dj yang nam c~nh ngung t\l

1. Danb pbap va eau true2. Phuong phap t6ng hCJp3. Tinh chat

14.2.3. HCJp chat dj yang nam c~nh hai dj to - azol

1. Phuong phap t6ng hCJpa) HCJpcMit 1,2- oxazol duCJcdieu che tit ph an dng cua hidrazin

hay hidroxylamin vai 1,3- dicacbonylb) HCJp chat 1,2- oxazol duCJc dieu che tit phan dng yang hoa cua

nitrinoxit vai axetylenc) HCJPchat 1,3- azol duCJc t6ng hCJpMng cach lo~i nuac cua

1,4- dicacbonyl2. Tinh chat v~t ly3. Cau truc cua azol

4. Tinh chat hoa h9C

14.2.4. HCJpchat dj yang sau c~nh - pyridin1. Phuong phap t6ng hCJp2. Tinh chat v~t ly cua pyridin3. Cau truc cua pyridin4. Tinh chat hoa h9C

a) Tinh baw cua pyridinb) Phan dng the electrophinc) Phan dng the nucleophind) Phan dng khlie) Phfm dng oxi hoa0 Phfm dng cua goc ankyl cua ankylpyridin

14.2.5. HCJp chat dj yang sau c~nh ngung t\l1. Phuong phap t6ng hCJp

a) Phuong phap t6ng hCJpSkraupb) Phfm dng Dobner - Millerc) Phan dng Friedlanderd) Phfm dng Bischler - Napieralaki

2. Tinh chat hoa h9Ca) Phan dng the electrophinb) Phfm dng the nucleophinc) Phan dng khlid) Phan dng oxi hoa

114114118119119120121

121122123126126

126

127

128129130131133133134135136136136138140141141142142142143143144144145146146146

Page 5: Cơ sở hoá học hữu cơ : Tập III

14.2.6. HelP chat d~ yang sau c~nh hai di to1. Phuong phIlp t6ng helP2. Tinh chat bOa hQc

14.2.7. Tinh chat d~c trung cua helP chat d! yang

14.3. Pyron14.3.1. Phuong phIlp t6ng helP

1. T6ng helP a- pyron2. T6ng helP y- pyron

14.3.2. Tinh chat cua pyron14.4. Ancaloit

14.4.1. Ancaloit co d! yang nam c~nh, mi?t nito14.4.2. D! yang nam c~nh, hai nito14.4.3. Ancaloit d! yang sau c~nh, mi?t nito14.4.4. Ancaloit d! yang sau c~nh, ngung t',1 chung mi?t nitd14.4.5. Ancaloit d! yang naill, sau c~nh ngung t',1 mi?t d! to nito14.4.6. Ancaloit co hai d! yang mi?t nito14.4.7. Ancaloit ba d! yang ngung t',1 vdi ba nita

14.5. Chat khang sinh14.5.1. Penixylin14.5.2. Tetraxyclin

14.5.3. Levomixetin (clomixitin)

14.5.4. Streptomixin

Chuang 15. Hidroxo va hidratcacbon

15.1. Hidroxo

15.1.1. Phuong phIlp t6ng helP hidroxo1. Phan ling ngung t',1 andol2. Phan ling ngung t',1 axyloin3. Ph an ling ngung t',1 benzoin4. Khti tung phan diandehit hay dixeton ho~c oxi hoa tung phan dial

15.1.2. Tinh chat bOa hQc

1. Phan ling 100;linudc (dehidrat boa)2. Phan ling phan cat m~ch3. Phan ling yang bOa

15.2. Hidratcacbon15.2.1. Monosaccarit

1. Cau hlnh d~ng hd cua monosaccarit2. Cau hlnh d~ng yang ctla monosaccarit3. Cau d~ng cua monosaccal'it4. S1j chuyen hoa anome5. Cau d~ng cua furanozo6. Tlnh chat hoa hQc cua monosaccarit

. a) Phan ling ete bOa

146148149151152152152153153156156156

156157157158

158158159

159159

160

161161

161162163

163163163165165167168168174181185189190190

Page 6: Cơ sở hoá học hữu cơ : Tập III

b) Phan ung este h6ac) Phan ung t~o thanh axetal va xetal vangd) Phan ung t~o thanh phenylhidrazon va ozazone) Phan ung oxi hOa0 Phan ung khitg) Phan ung tang m~ch cacbonh) Phan ung rut ngan m~ch

15.2.2. Oligosaccarit1. Mantozo2. 8accarozo3. Lactozo4. Xenlobiozo5. Raffinozo

6. Chat duang photphat7. Phuong phap xac djnh cac hIJp chat duang

15.2.3. Polysaccarit1. Xenlulozo2. Tinh bqt

a) Amylozob) Amylopectinc) Xyclodextrin

15.3. Quang t6ng hIJp cac chat duang

15.4. Qua trinh chuyen hOa cua gluxit

Chuang 16. Aminoaxit - protit

16.1. Aminoaxit

16.1.1. Danh phap16.1.2. Phuong phap t6ng hIJp

1. Amin h6a cac halogenua axit2. Phuong phap este phtalimidomalonic cua Gabriel3. Phuong phap xyanhidrin4. Phuong phap Miscellaneous5. Khit cac hIJp chat nitro, oxim hay hidrazon cua a- andehit axit hay

a- xetoaxit

6. Tac d1,mgeste axetoaxetic the vClimu6i phenyldiazoni7. Cqng amoniac vao axit chua no8. 81,(phan giai cae hIJp chat aminoaxit quang ho~t

16.1.3. Cau truc cua aminoaxit va tfnh chat v~t Ii16.1.4. Tfnh chat h6a hQC

1. Tfnh axit - bazo cua aminoaxit2. Tinh chat cua nh6m -COOH3. Tinh chat ciia nhOm amin

a) Axyl hOa nh6m amin thanh amit trong diEmki~n kiem

193194196199202202203204204206207209209210215215216221221223225226

227

231231234

234235237237

238238239239240241

241244245245

Page 7: Cơ sở hoá học hữu cơ : Tập III

b) Ankyl hOa nhom am in bang CH31 hay (CH3)z804 khi co kiem4. Tac dl,mg cua nhi~t5. Pha.n ung mau cua aminoaxit

a) Phan ung biuretb) Phan ung xangtoproteitc) Phan ung Milond) Phan ung v<'lininhidrin

6. Phan ung d~c trung cua aminoaxit16.2. Peptit

16.2.1. Phuong philp t6ng h<Jp peptit16.2.2. Cau truc cua pep tit16.2.3. Tfnh chat cua peptit16.2.4. Phuong philp xac dinh cau truc peptit

16.3. Protit

16.3.1. Phan lol;\i protit1. Protein2. Proteit

16.3.2. Cau truc cua protit1. Cau truc b~c nhat2. Cau truc b~c hai3. Cau truc b~c ba va cao hon

16.3.3. Ttnh chat cua protit1. Ttnh chat luong tinh2. Phan ung mau3. Tfnh tan

4. 81,ibien ttnh cua protit5. 81,iket tua protit6. Hol;\t tinh sinh 11

16.4. Nucleoproteit - Axit nucleic16.4.1. Nucleoproteit16.4.2. Nucleotit16.4.3. Nucleozit

..16.4.4. Axit nucleic16.4.5. Vai tro sinh hc;>ccua axit nucleic

16.5. Enzym - Coenzym16.6. Thuc an nhan tl;\O16.7. Vitamin

16.7.1. Vitamin C

16.7.2. Vitamin Bl16.7.3. Vitamin B1216.7.4. Vitamin E16.7.5. Vitamin K16.7.6. Vitamin D16.7.7. Vitamin A

245245246246246246246248250250255257258261261261263263263264266268268269269269269270273273275276276277281

284

285285286286286286288288

Page 8: Cơ sở hoá học hữu cơ : Tập III

16.7.8. Vitamin F16.7.9. Vitamin P

Chuang 17. Hqp chat cao phfm tic

17.1. Stj khac nhau giua h<;1pchat cao va thap phan tit

17.2. Danh phap polyme

17.3. Phan lo:;\i polyme17.3.1. Phv thuQc thanh phan17.3.2. Phv thuQc vao cau trUc m:;\ch phan tit17.3.3. PhV thuQc vao tfnh chat ly hQC

17.3.4. PhV thuQc vao thanh phan m:;\ch chlnh cua phan tit17.4. Phtl<1ng phap t6ng h<;1ppolyme

17.5. Monome - nguyen li~u dau cho t6ng h<;1ppolyme

17.6. Phlm ung trimg h<;1p17.6.1. Phan ung trimg h<;1pgoc

1. Cac giai do:;\n trimg h<;1pgoc2. Toc dQ phan ung trimg h<;1p3. Nhung nhan to anh huang tbi phan ung trimg h<;1p

a) Anh huang cua nhi~t dQb) A.nh huang cua chat klch thfchc) Anh huang cua Dong dQ maDamed) Anh huang cua ap suat

4. Cac phuong philp kfch thfch trung h<;1pa) Kfch thfch bang nhi~tb) Kfch thfch bang anh sangc) Kfch thfch buc x:;\

5. Phan ung chuyen m:;\cha) Chuyen m:;\ch qua maDameb) Chuyen m:;\ch qua chat kfch thfchc) Chuyen m:;\ch qua dung moid) Chuyen m:;\ch qua polyme

6. Chat dieu hba - Chat kim ham - Chat che't m:;\ch. 7. Cau truc maDame va kha Dang trung h<;1p

a) Phan ung trung h<;1pxay ra khi nhi~t trung h<;1pduongb) Toc dQ trung h<;1pphv thuQc vao hi~u ung electron cua nh6m

the

c) Toc dQ trung h<;1pphV thuQc vao cau truc l~p the cua monomed) Toc dQ trung h<;1pphv thuQc vao ban chat cua goc ttj doe) Cau truc cua mono me anh huang Ibn den cau truc cua m:;\ch

phan tit polyme17.6.2. Phan ung trung h<;1pcation17.6.3. Phan ung trung h<;1panion

17.6.4. Phan ung trung h<;1pdieu hba l~p the

288289

291

292

292292293293293294

294

297297298299300300300301301301301302302303303303304304304306306

306

307307

307308309310

Page 9: Cơ sở hoá học hữu cơ : Tập III

17.7. PMn ang dong trimg hqp17.7.1. Phan ang dong trimg hqp g6c17.7.2. Phan ang dong trimg hqp ion

17.8. PMn ang trimg hqp ph an b~c (hay doi chuyen)

17.9. PhuC1ng phIlp th\iC nghi~m tieD hi'mh trimg hqpa) Phuong phIlp trimg hqp khOib) PhuC1ng phIlp trimg hqp trong dung djchc) PhuC1ng phIlp trimg hqp nhii tuC1ngd) Phuong phIlp trimg hqp huyen phile) Phan ang trung hqp trong tu<1ng khff) Phan ang trung hqp trong tu<1ng ran

17.10. PMn ang trung ngung17.10.1. Phan ang trung ngung can bang17.10.2. Phan ang ph\! trong phan ang trung ngung17.10.3. PhuC1ng philp tieD hi'mh trung ngung can bang

a) Trung ngung Dong chayb) Trung ngung trong dung djchc) Trung ngung trong tu<1ng ran

17.10.4. Phan ang trilng ngung khOng can bang

17.11. Cali truc phan tii polyme17.11.1. Cali hinh cua phan tii polyme17.11.2. Cali d~ng polyme

17.11.3. Cali truc ngo~i vi ph an tii17.12. Tr~ng thai v~t If cua polyme

17.12.1. Tr~ng thai v~t If17.12.2. S\i bien d~ng cua polyme17.12.3. Duong cong co hQc

17.13. Tfnh chat cua polyme17.13.1. Tfnh tan

17.13.2. DQ nMt cua polyme

17.13.3. Kh6i luqng phan tii cua polyme17.13.4. DQ da ph an tii luqng1,,7.13.5. Tfnh chat cC1hQc cua polyme

17.13.6. S\i lao hoa cua polyme17.13.7. Phan ang chuyen hoa hoa hQc cua polyme

17.14. Elastome - Caosu

17.15. Chat cleo

1. Polyetylen (PE)2. Polystyren3. Polyvinylclorua4. Polytetrafloetylen5. Polyphenolfomandehit

17.16. TC1- sqi

313313316318

319319319320321322322322323325326326326326326328328329

330

332332332333334334334335335

336

336337

337

341341342342343343346

Page 10: Cơ sở hoá học hữu cơ : Tập III

1. SQi bOng2. Td tam

3. SQi len

4. SQi bien tfnh (hay sQi nhan t~o)5. Td tong hQp

17.17. Nh~a trao doi ion

346346347347348349

Chuang 18. Phuong phap pho trong hoa huu cO

18.1. Pho di~n tit

18.2. Quang pM electron18.2.1. S~ chuyen muc :re ~ :re"

18.2.2. S~ chuyen muc n ~ :re"

18.3. Pho hong ngo~i (IR)18.3.1. S~ dao dQng phan tit18.3.2. Pho IR cua cac lo~i hQp chat

1. Ankan2. Anken

3. Ankyn4. Halogenua ankyl5. Ancol va ete6. Andehit xeton

7. Axit cacboxylic va este18.4. Pho cQng huang tit h~t nhan

18.4.1. Ph6 cQng huang tit proton HNMR18.4.2. DQ chuyen dich hoa hQc18.4.3. Tudng tac spin- spin18.4.4. PM cQng huang tit cacbon CNMR

18.5. Quang pM khOi (MS)

353

355357359362362366366366367367367368370372372374376383388