Professional Documents
Culture Documents
Huuco 6 Cicloalcan
Huuco 6 Cicloalcan
104
n3
Xicloankan (Mch chnh l mch vng. Cc nhm gn vo vng coi l cc nhm th gn vo xicloankan)
Xiclopentan (C5H10)
H3C (C9H18)
CH2CH3
1,3-imetyl-2-etylxiclopentan
Xiclohexan (C6H12)
H3C HC H3C
CH2CH3
Xiclooctan (C8H16)
Xicloheptan (C7H14)
Gio khoa ha hu c
105
Tnh cht ha hc ca xicloankan (nht l cc vng 5, vng 6, cng nh cc vng ln hn) c bn ging nh ca ankan. Ngha l xicloankan thng ch cho c phn ng th vi halogen X2 khi c s hin din ca nh sng hay un nng, xicloankan khng b oxi ha bi dung dch KMnO4. Tuy nhin vi cc xicloankan vng nh (vng 3, vng 4, nht l vng 3) cn c tnh cht nh mt hirocacbon khng no, v n cho c phn ng cng to sn phm m vng. Nguyn nhn ca tnh cht ha hc ny l do cc vng nh c sc cng gc ln (sc cng Baeyer, gc CCC trong xiclopropan bng 600, gc CCC trong xiclobutan bng 900, ng l gc CCC ca lin kt n l 109028 ging nh trong ankan) nn khng bn. Chng tham gia phn ng cng hay phn ng ng phn ha to sn phm m vng bn hn. VII.4.1. Phn ng chy CnH2n +
3n O2 2
t0
nCO2
nH2O
VII.4.2.. Phn ng th
Br
HBr
(C5H9Br) 1-Bromxiclopentan
0 450 C
Hirobromua
H2O
Cl2 Clo
ah sag n n
Cl (C4H7Cl) Cloxiclobutan
Xiclopropan v xiclobutan cho c phn ng cng hiro (H2) to ankan tng ng vi s hin din ca niken (Ni) hay bch kim (Pt) lm xc tc v un nng, nhng un nng mnh hn so vi khi cng hiro vo anken. Cc xicloankan khc (xiclopentan, xiclohexan,...) khng cho c phn ng ny.
Gio khoa ha hu c
106
Xiclopropan cho c phn ng cng vi Br2 (trong dung mi CCl4), vi dung dch HX m c (HCl, HBr, HI), cng nh cho c phn ng cng vi dung dch axit sunfuric m c (H2SO4). Do xiclopropan cng lm mt mu dung dch Br2 nhng chm hn so vi anken, ankin.
+
Xiclopropan
H2
Hiro
Ni (Pt) t
0
(C3H6)
(800C)
CH3CH2CH3 (C3H8)
Propan
+ (C4H8)
Xiclobutan , Xiclopentan
H2
Hiro
Ni (Pt)
0 t (120 C) 0
CH3CH2CH2CH3
(C4H10) n-butan
H2 Ni (Pt), t0 Xiclohexan
+ (C3H6)
Xiclopropan
Br2
CCl 4
Dung d brom ch
Br-CH2-CH2-CH2-Br (C3H6Br2)
1,3-ibrompropan Br2 / CCl4
,
Xiclobutan Xiclopentan
, Xiclohexan
+ Xiclopropan
HX ()
Axit halogenhiric a a m c Axit sunfuric
CH3-CH2-CH2-X
1-Halogenpropan n-Propyl sunfataxit
HX
Khi cho xiclopropan i qua nhm oxit (Al2O3) 1000C, n s chuyn ha thnh cht ng phn l propen.
Gio khoa ha hu c
107
Al2O3 , 1000C
(C3H6)
Xiclopropan
VII.5. ng dng
T xiclohexan, metylxiclohexan thc hin phn ng ehiro-ha vi cht xc tc, nhit thch hp c th thu c cc hirocacbon thm tng ng l benzen v toluen (phn ng reforming)
Xt, t0 (MoO3/Al2O3)
+ (C6H6)
Benzen Pt, t0, p
3H2
Hiro
(C6H12)
Xiclohexan
CH3 (C7H14)
Metylxiclohexan
CH3 (C7H8)
Toluen
3H2
Hiro
VII.6. iu ch VII.6.1. Cho dn xut ihalogen ca ankan, trong 2 nguyn t halogen cch xa nhau, tc dng vi natri (Na) hay km (Zn) s thu c xicloankan tng ng (ging nh phn ng Wurtz)
CH2 CH2 CH2 CH2 CH2 CH2 CH2 Br Cl CH2
1,3-iclopropan
Cl Zn
Ke m NaI Ancol loa g, 1250C n
ZnCl2 Ke clorua m
Br + 2Na
Natri
1,5-ibrompentan
Xiclopentan
Phng pha na thg dug e u che p y n c n ie xiclopropan. Dug kim loa ke n i m cho hie suatohn so vnatri. Vca vog kha, hie suapha g ratha. u t t i i c n c u t n n t p
Gio khoa ha hu c
108
VII.6.2. Nhit phn mui canxi ca axit icacboxilic, to xeton vng, ri kh xeton vng ny bng hn hng km trong axit clohiric
COO Ca COO CO +
t0
CH2 CH2
CH2 CH2
CO CH2
+ CH2
CaCO3
Canxi cacbonat
Canxi aipat
Xiclopentanon
Xiclo pentanon
4[H]
Zn-Hg/HCl
CH2 + H2O
COO Ca COO
t
0
CO
CaCO3
Canxi cacbonat
Canxi glutarat
CH2
Zn-Hg/HCl (Clemmensen)
CH2 CH2
CH2
H2O
Xiclobutanon
Xiclobutan
+
(C6H6) Benzen
4H2
Hiro
Ni t0 (C6H12) Xiclohexan
OH
Phenol
3H2
Hiro
Ni, t0
OH
Xiclohexanol
OH
Xiclohexanol
H2O
N c
+
Xiclohexen
H2
Hiro
Ni,t0
Xiclohexan
Gio khoa ha hu c
109
Ghi ch: Hn hng ca mt kim loi l hp kim ca kim loi v thy ngn. Thy ngn l kim loi duy nht hin din dng lng iu kin thng thng, do n ha tan c nhiu bt kim loi to hp kim tng ng. Hn hng cn gi l amalgam.
Th d: hn hng natri: hp kim natri v thy ngn hn hng thic: hp kim thic vi thy ngn hn hng bc: hp kim bc vi thy ngn
Bi tp 49 C ba bnh, mi bnh cha mt kh ring, gm: propan, xiclopropan v propen. Hy nhn bit cc bnh kh trn bng phng php ha hc. Vit cc phn ng xy ra. Bi tp 49 Phn bit cc kh sau y ng trong cc bnh mt nhn: Axetilen, Etilen, Etan v Xiclopropan. Vit cc phn ng xy ra. Bi tp 50 A l mt xicloankan. T khi hi ca A so vi nit bng 3. A tc dng vi Cl2, khi chiu sng, theo t l mol nA : nCl2 = 1 : 1 ch to mt dn xut monoclo duy nht. Xc nh cng thc cu to ca A. vit phn ng xy ra. c tn cc tc cht, sn phm. (C = 12 ; H = 1 ; N = 14) S: Xiclohexan Bi tp 50 X l mt hirocacbon. Mt th tch hi X vi 2,625 th tch metan c cng khi lng (cc th tch hi, kh trn o cng iu kin nhit , p sut). a. Xc nh CTCT ca X, c tn X. Bit rng X khng lm mt mu tm ca dung dch KMnO4. b. Y l mt ng phn ca X. Vit cc phng trnh phn ng theo s sau y (mi mi tn l mt phn ng): X dd Br2 X1 dd NaOH, t0 X2 CuO, t0 X3 O2, Mn2+ X4
Y dd Br2 Y1
dd NaOH, t0
Y2 CuO, t0
(C = 12 ; H = 1) S: X: Xiclopropan
Bi tp 51 A, B l hai hirocacbon ng ng lin tip (MA < MB). 1,568 lt hn hp hi X (ktc) gm hai cht A, B c t chy hon ton bng 44,8 lt khng kh (ktc) c d. Th tch hi nc thu c bng th tch kh CO2 (cng iu kin). Cho tt c cc kh thu c sau phn ng chy vo mt ng p trn chu nc. Th tch kh trong ng l 45,981 lt 150C, ct nc trong ng cao hn so vi mc nc ngoi chu l 4,08 cm (xem hnh). p sut kh quyn l 750 mmHg, p sut hi nc bo ha 150C l 12,7 mmHg. Thy ngn c t khi l 13,6.
Gio khoa ha hu c
110
a. Xc nh CTPT, CTCT ca A, B. Bit rng B tc dng Cl2 theo t l mol 1 : 1 ch to mt dn xut monoclo v B khng tc dng vi dung dch kali pemanganat. b. Tnh % khi lng mi cht trong hn hp X. Vit CTCT cc ng phn ca A, B v c tn cc ng phn ny. Coi N2, O2, CO2 khng ha tan trong nc. Khng kh gm 20% O2, 80% N2 theo th tch. (C = 12 ; H = 1)
c.
Bi tp 51 Hn hp A gm hai cht X, Y lin tip trong dy ng ng ca benzen. t chy hon ton 2,9 gam hn hp A bng lng O2 ly gp i so vi lng cn. Cho tt c cc kh sau phn ng chy vo mt ng p trn chu nc, th tch phn kh trong ng l 12,66 lt 250C. Mc nc trong ng thp hn mc nc ngoi chu l 68 mm (xem hnh). p sut kh quyn l 760 mmHg. p sut hi nc bo ha 250C l 23,7 mmHg. Khi lng ring ca thy ngn l 13,6 g/cm3. a. Xc nh CTPT ca X, Y. Vit cc CTCT c th c ca X,Y. c tn cc cht ny. b. Tnh % khi lng ca mi cht trong hn hp A. Coi O2, CO2 khng ha tan trong nc. Ly 3 s l trong s tnh ton. (C = 12; H = 1)
Y1
dd NaOH, t0
Y2 (n chc)
Gio khoa ha hu c
111
Xc nh CTCT ca X, Y. Vit phn ng theo s trn v c tn X, X1, X2, Y, Y1, Y 2. Cc phn ng xy ra hon ton. (C = 12; H = 1; O =16; Ca = 40) S: m = 2,1g; X: xiclopropan, Y: propen
Bi tp 52 Hn hp X gm hai hirocacbon A, B ng phn nhau. Ly m gam X em t chy cn dng V (lt) khng kh (ktc). Cho sn phm chy hp th vo 500 ml dung dch Ba(OH)2 0,24M, thu c kt ta mu trng v dung dch D. Dung dch D cho tc dng vi dung dch KOH d, thu c 7,88 gam kt ta na. Khi lng dung dch D nh hn khi lng dung dch Ba(OH)2 lc u l 5,84 gam. a. Tnh m, V. b. Xc nh CTPT ca A, B. Bit rng 4 th tch hi X c cng khi lng vi 7 th tch kh oxi (o trong cng iu kin v nhit v p sut). c. Cho bit c cc phn ng theo s sau y: H2, Ni, t0 (1) A1 Cl2 , as, 1: 1 (2) A2 dd NaOH, t0 (3) A3(n chc) A
B A3
dd Br2 (7)
(4)
B1
(8)
B2
B3
B3
A3
Mi mi tn l mt phn ng. Xc nh CTCT ca A, B v vit cc phn ng xy ra theo s trn. Cho bit A khng tc dng dung dch Br2 cng nh dung dch KMnO4, B c cu to dng cis. Cc phn ng xy ra hon ton. Khng kh gm 20% O2, 80% N2 theo th tch. (C = 12; H = 1; O = 16; Ba = 137) p s: m = 2,24g; V = 26,88 lt; A: Xiclobutan; B: Buten-2
CU HI N PHN VII
1. Xicloankan l g? Cho th d minh ha. 2. Hy cho bit cng thc chung dy ng ng ca cc cht sau y: Xiclohexan; Xiclohexen; Benzen; Stiren; Etinyl benzen (Phenyl axetilen); n- Hexan; Isopren; Isobutilen; Axetilen; Vinylaxetilen.
Gio khoa ha hu c
112
CH3
CH CH2
H3C
CH3
4. Vit CTCT ca cc cht sau y: a. 1-Metyl-2-isopropylxiclobutan b. 1-n-Butyl-3-isobutylxiclohexan c. n-Amylxiclooctan d. Xiclopentylxiclopentan e. 1,3,5-Trimetylxiclohexan f. 1-Vinyl-3-alylxicloheptan g. Toluen h. Cloropren (2-Clobut-1,3-ien) 5. Vit phng trnh phn ng theo s sau: X (C3H6) dd Br2 Y dd NaOH Z
CuO, t0 CuO, t0
A (C3H6)
dd Br2
dd NaOH
6. C hp cht hu c no trong phn t khng cha lin kt i, lin kt ba m cho c phn ng cng hay khng? Gii thch v cho th d minh ha cho cu tr li. 7. A l mt hirocacbon. t chy ht 1 mol A, thu c 4 mol CO2 v 4 mol H2O. Xc nh CTCT ca A. Bit rng A khng phn nhnh, A khng lm mt mu dung dch KMnO4 v t A c th iu ch cc cht khc theo s sau:
A D
B E
dd KOH HBr
D C
F (SP chnh)
Gio khoa ha hu c
113
khi lng bnh dung dch nc vi tng 17,05 gam v trong bnh c 27,5 gam kt ta. Cn nu t chy hon ton m gam A cn dng 36,96 lt O2 (ktc). a. Xc nh CTPT ca hai hirocacbon trong hn hp A. b. Tnh % khi lng mi cht trong hn hp A. c. Tnh m. d. Vit tt c cc ng phn c th c ca cht c khi lng phn t ln trong A. c tn cc cu to ny. (C = 12; H = 1; Ca = 40; O = 16) S: 27,27% C3H6; 72,73% C4H8; m = 15,4g
9. Hn hp A gm 3 cht X, Y, Z thuc dy ng ng xicloankan: X (CxH2x); Y (CyHy); Z (CzH2z). Trong x < y < z ; Z v X cch nhau k cht trong dy ng ng. t chy hon ton a lt hi hn hp A (ktc) th cn dng b gam O2. 1,4b 3a 1,4b k<x< a. Chng minh: 3a 3a b. Xc nh CTCT ca X, Y, Z v c tn cc cht ny. Cho bit Y cho c phn ng cng H2 (c Ni lm xc tc, un nng); k = 2 v X, Y, Z c mch cacbon khng phn nhnh. c. Tnh % khi lng mi cht trong hn hp A nu a = 10,08 lt; b = 100,8 gam; S mol ca Y bng trung bnh cng s mol ca hai cht X, Z v cng d kin nh cu (b). (C = 12; H = 1; O = 16) S: 14,29% C3H6; 28,57% C4H8; 57,14% C6H12 10. t chy hon ton 1,04 gam mt cht hu c D cn va 2,24 lt kh O2 (ktc), ch thu c kh CO2, hi H2O theo t l th tch V CO2 : V H 2O = 2 : 1 cng iu kin
nhit v p sut. Xc nh CTPT, CTCT ca D, bit t khi hi ca D so vi hiro 52, D cha vng benzen v tc dng c vi dung dch brom. Vit phng trnh phn ng xy ra. (C = 12 ; H = 1 ; O = 16) ( TSH khi A, nm 2005) S: Stiren
11. Hn hp X gm hai anken k tip nhau trong dy ng ng. t chy hon ton 5 lt hn hp X cn va 18 lt kh oxi (cc th tch kh o cng iu kin nhit , p sut). 1. Xc nh cng thc phn t ca hai anken. 2. Hirat ha hon ton mt th tch X vi iu kin thch hp thu c hn hp ru Y, trong t l v khi lng cc ru bc mt so vi ru bc hai l 28 : 15. a) Xc nh % khi lng mi ru trong hn hp ru Y. b) Cho hn hp ru Y th hi qua CuO un nng, nhng ru no b oxi ha thnh anehit? Vit phng trnh phn ng. (C = 12 ; H = 1 ; O = 16) ( TSH khi A, nm 2004) S: 1. C2H4 ; C3H6 2.a) 34,88% i-C3H7OH, 53,49% C2H5OH, 11,63% n-C3H7OH
Gio khoa ha hu c
114