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Chuyen de 3 Dan Xuat Halogen Ancol Phenol LTDH
Chuyen de 3 Dan Xuat Halogen Ancol Phenol LTDH
Chuyen de 3 Dan Xuat Halogen Ancol Phenol LTDH
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III. TNH CHT HA HC 1. Phn ng th nguyn t halogen bng nhm OH Phn ng vi H2O nng
Dn xut nhm 1 v 3 khng phn ng vi H2O mi nhit
Anlyl Clorua
t C6H5 CH2 Cl + H2O C6H5 CH2 OH
0
+ HCl
Dn xut nhm 1 v 2 tc dng c vi dung dch kim long nng. Trong nhm 2
phn ng d dng hn nhm 1.
t RX + NaOH ROH + NaX t CH3CH2Br + NaOH CH3CH2OH + NaBr t CH2 = CH CH2 Cl + NaOH CH2 = CH CH2 OH
0 0 0
+ NaCl
Dn xut nhm 3 khng phn ng th vi dung dch kim k c khi un nng 2. Phn ng tch hirohalogenua PTTQ: (i vi dn xut halogen no, n chc, mch h)
C2 H5OH CnH2n+1X + KOH CnH2n + t0
KX + H2O
Ch : Quy tc Zaixep: Khi tch HX ca dn xut halogen th u tin tch X vi nguyn t H C bn cnh bc cao hn lm sn phm chnh Khi tch HX ca dn xut halogen thu c 1 anken duy nht (khng tnh ng phn hnh hc) th dn xut halogen l no, bc 1 hoc i xng. 3. Phn ng vi kim loi Mg (mi trng ete khan)
t RX + Mg R Mg X
0
ANCOL
I. KHI NIM V PHN LOI 1. Khi nim Ancol l nhng hp cht hu c trong phn t c nhm OH lin kt trc tip vi nguyn t C no. CT chung: CnH2n + 2 - 2k - x(OH)x hoc R(OH)x (Trong k l s lk pi + s vng, x n )
- x(OH)x
- 2kOH
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CH3 CH2 CH2 CH2OH: CH3 CH2 CH(CH3) OH: CH3 C(CH3)2 OH: 2. Phn loi
ru l s ml ru nguyn cht c trong 100 ml dung dich ru. Ancol no, n chc, mch h (CnH2n+1OH): V d: CH3OH . . . Ancol khng no, n chc mch h: CH2 = CH CH2OH Ancol thm n chc: C6H5 CH2OH Ancol vng no, n chc: OH xiclohexan Ancol a chc: CH2OH-CH2OH (etilen glicol), CH2OH-CHOH-CH2OH (glixerol) 3. Mt s trng hp khng bn ca Ancol Ancol dng: R CH = CH OH (ancol bc 1 c OH lin kt vi C khng no) R CH = CH OH R CH2CHO (anehit) Ancol dng: R CH2 CH(OH)2 (ancol c 2 nhm OH lin kt vi 1 C ngoi cng) R CH2 CH(OH)2 R CH2 CHO (anehit) + H2O Ancol dng: R CH = C(OH) R (ancol bc 2 c OH lin kt vi C khng no pha trong) R CH = C(OH) R R CH2 CO R(xeton) Ancol dng: R CH2 C(OH)2 R (ancol c 2 nhm OH lin kt vi 1 C pha trong) R CH2 C(OH)2 R R CH2 CO R(xeton) + H2O Ancol dng: R CH2 CH(OH)3 (ancol c 3 nhm OH lin kt vi 1 C) R CH2 CH(OH)3 R CH2COOH (axit) + H2O II. NG PHN V DANH PHP 1. ng phn: Ch c ng phn cu to (gm ng phn mch C v ng phn v tr nhm OH). Th d C4H10O c 4 ng phn ancol CH3 CH2 CH2 CH2 OH; CH3 CH(CH3) CH2 OH CH3 CH2 CH(CH3) OH; 2. Danh php: Danh php thng: Ancol + tn gc + ic Danh php thay th (IUPAC): V tr nhnh + tn nhnh (nu c) + tn H.C tng ng + v tr OH + ol
4 3 2 1
Th d: C H 3 C H(CH 3 ) C H 2 C H 2OH (3-metylbutan-1-ol) III. TNH CHT 1. Tnh cht vt l Tan nhiu trong nc do to c lin kt H vi nc. tan trong nc gim dn khi s nguyn t C tng ln. Ancol c kh nng to lin kt hiro vi phn t ancol khc v vi H2O nn n c nhit si cao hn so vi hidrocacbon, dn xut halogen, ete, andehit, xeton v c este. 2. Tnh cht ha hc a. Phn ng vi kim loi kim 2R(OH)x + 2xNa 2R(ONa)x + xH2 Trang 3
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Mui R(ONa)x d phn ng vi H2O ti to li ancol R(ONa)x + xH2O R(OH)x + xNaOH b. Phn ng vi dung dch axit ( phn ng este ha) Phn ng vi axit v c C2H5 OH +
t H Br C2H5Br + H2O
0
Phn ng vi axit hu c
t R OH + R COOH R COO R + H2O
0
c. Phn ng tch nc Tch H2O ca 1 phn t ru no n chc 1700C xc tc H2SO4 c nng. to thnh anken:
H 2SO4 , 170 C CnH2n+1OH CnH2n + H2O
0
H2O
m gi '
2. iu ch
iu ch t anken tng ng:
H 2SO4 , t CnH2n + H2O CnH2n+1OH
0
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iu ch etilen glicol t etilen 3C2H4 + 2 KMnO4 + 4H2O 3C2H4(OH)2 + 2MnO2en +2KOH iu ch glixerol i t anken tng ng l CH2=CH CH3 hoc thy phn lipit
t CH2 = CH CH3 + Cl2 CH2 = CH CH2Cl
0
CH2 = CH CH2Cl + Cl2 + H2O CH2Cl CH(OH) CH2Cl + HCl CH2Cl CH(OH) CH2Cl + 2NaOH CH2(OH) CH(OH) CH2(OH) + 2NaCl Glixerol
t T CH4: 2CH4 + O2 2CH3OH , 200 atm , 400 C T CO: CO + 2H2 Zn CH3OH
o
m Ancol + m Na = m R 'n + m H 2
V d 1: Cho 1 lt cn 92o tc dng vi Na d. Cho khi lng ring ca ru etylic nguyn cht l 0,8 g/ml. th tch kh H2 c ktc l
A. 224,24 lt B. 224 lt C. 280 lt D. 228,98 lt
Li gii:
1 lt cn 92o cha 920 ml C2H5OH v 80 ml nc S mol C2H5OH l S mol H2O l PTP: C2H5OH + Na C2H5ONa + 16 mol H2O + Na 1 H 2 2 8 mol
920.0,8 = 16 mol 46
80 = 4,444 mol 18
NaOH
1 H 2 2 Trang 5
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4,444 mol
2,222 mol
p n D
V d 2: Cho 15,6 gam hn hp hai ancol (ru) n chc, k tip nhau trong dy ng ng tc dng ht vi 9,2 gam Na, thu c 24,5 gam cht rn. Hai ancol l
A. CH3OH v C2H5OH C. C2H5OH v C3H7OH B. C3H7OH v C4H9OH D. C3H5OH v C4H7OH
R OH + Na R ONa + 1/2 H2
BTKL mHiro = 24,5 (15,6 + 9,2) = 0,3 gam nHiro = 0,15 mol
15,6 = 52 R = 35 0,3
hai ancol l: C2H5OH (M = 46) v C3H7OH (M = 60) V d 3: Cho 18,0 g hn hp hai ancol gm mt ancol no n chc v mt ancol n chc c mt lin kt i trong phn t c s mol bng nhau tc dng ht vi Na thu c 4,48 lt H2 ktc. Xc nh CTCT hai ancol. Li gii: t CTPT chung ca hai ancol l R OH.
Ta c: 2 R OH + 2Na 2 R ONa + H2
4, 48 = 0, 4 mol 22, 4
Khi tch H2O ca Ancol 1700C xc tc H2SO4 thu c An ken Ancol no, n chc.
Nu ch thu c 1 anken duy nht Ancol no, n chc l Ancol bc 1 hoc i xng.
m Ancol = m Anken + m H 2O
H2O k(k + 1) 2
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V d 2: un nng 12,90 gam hn hp X gm 2 ancol no, n chc, bc 1, l ng ng k tip trong H2SO4 c 140oC thu c 10,65 gam hn hp Y gm 3 ete (h = 100%). Xc nh cng thc phn t ca hai ancol. Li gii:
t CT ca hai ancol l R OH
BTKL mnc = mancol - mete = 12,9 - 10,65 = 2,25 (gam) nnc = 0,125 mol 129 = 516 hai ancol l: C2H5OH v C3H7OH 025
ancol
V d 3: Cho hn hp hai anken ng ng k tip nhau tc dng vi nc (c H2SO4 lm xc tc) thu c hn hp Z gm hai ru (ancol) X v Y. t chy hon ton 1,06 gam hn hp Z sau hp th ton b sn phm chy vo 2 lt dung dch NaOH 0,1M thu c dung dch T trong nng ca NaOH bng 0,05M. Xc nh Cng thc cu to thu gn ca X v Y Li gii:
Ta c: nNaOH ban u = 0,2 mol; nNaOH d = 0,1 mol nNaOH p/ = 0,1 mol CO2 + 2 NaOH Na2CO3 + H2O 0,05
0,1
Ta c n Ancol =
14 n + 18
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mCuO mCu 16
V d: Cho m gam mt ancol (ru) no, n chc X qua bnh ng CuO (d), nung nng. Sau khi phn ng hon ton, khi lng cht rn trong bnh gim 0,32 gam. Hn hp hi thu c c t khi i vi hiro l 15,5. Gi tr ca m l A. 0,92 Li gii:
Gi CTPT ca ru CnH2n+1OH:
o
B. 0,46 x mol
C. 0,32
D. 0,64
20 .106 = 2. 105 gam 100 2.105 .n.2.46 = 113580. 24 g 162n 100.0,8.1000 .100 = 70% 113580, 24
V d 2: Cho m gam tinh bt ln men thnh ancol (ru) etylic vi hiu sut 81%. Ton b lng CO2 sinh ra c hp th hon ton vo dung dch Ca(OH)2 thu c 550 gam kt ta v dung dch X. un k dung dch X thu thm c 100 gam kt ta. Gi tr ca m l: A. 650 Li gii:
nH 2O ,t p / u ': (C 6 H 10 O5 ) n + nC 6 H 12 O6 xt 2nC 2 H 5 OH + 2nCO2
o
B. 550
C. 810
D. 750
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PHENOL
I. KHI NIM
Phenol l nhng hp cht hu c trong phn t c nhm OH lin kt trc tip vi nguyn t C vng benzen. CnH2n 7 OH ( n 6 ). Th d: C6H5OH (phenol), ...
Phenol cn gi l axit phenic, l mt axit yu (yu hn c H2CO3), khng lm qu tm i mu Khi nhm OH khng nh nhn m nh nhnh th hp cht khng thuc loi phenol m l ancol thm. Th d: C7H8O
CH2OH OH CH3 CH3 OH O
d
CH3
III. NG DNG V IU CH
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ng dng:
Phn ln phenol c dng sn xut poliphenolfomanehit (PPF: dng lm cht do, cht kt dnh) Phenol c dng iu ch dc phm, phm nhum, thuc n (2,4,6 trinitrophenol), cht kch thch sinh trng thc vt, cht dit c 2,4 D (axit 2,4 iclophenoxiaxetic), cht dit nm mc (nitrophenol), cht tr su b, ...
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10
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