01 Hoa - Huu - Co PDF

TRNG I HC NNG LM HU
D N HP TC VIT NAM H LAN
BI GING
HO HU C
Ngi bin son: Phan Th Diu Huyn
Hu, 08/2009
http://hhud.tvu.edu.vn
CHNG I. MT S NI DUNG C BN CA L THUYT
HA HU C
1.1. Phn ng hu c
1.1.1. Phn loi hp cht hu c
1.1.1.1. Phn loi theo nhm chc
Hp cht c bn ca Ho hu c l hydrocacbon. Cc cht khc c xem l
dn xut ca hydrocacbon, cc dn xut ny c hnh thnh bng cch thay th
mt hay nhiu nguyn t H trong hydrocacbon bng cc nhm chc khc, chng
hn: -OH, -CO-, -COOH, -NH2 ....
Khi phn t c mt nhm chc ta c hp cht n chc, c nhiu nhm
chc ng nht ta c hp cht a chc, c nhiu nhm chc khc nhau ta c hp
cht tp chc.
1.1.1.2. Phn loai theo mch C
Mach C c th h, vng, mch thng, phn nhnh, mch no, khng no ...
V c bn ngi ta phn thnh 2 loi chnh: mch h v mch vng, trong
mi loi li c nhng dng khc nhau.
- Mch h
+ Hp cht no: ch cha lin kt (lin kt n)
+ Hp cht khng no: cha lin kt bi (i, ba)
- Mch vng
+ ng vng: cc nguyn t to vng u l C
+ D vng: nguyn t to vng ngoi C cn cc nguyn t khc
Cc d t thng gp: O, S, N ...
1.1.2. Phn loi phn ng hu c
1.1.2.1. Phn ng th (S: Substitution)
Phn ng thay th nhm th ny bng nhm th khc
V d:
as
CH4 + Cl2 CH3 Cl + HCl (S R: th gc t do)
bt Fe
+ Cl2 Cl + HCl (SE: th electronphin)
CH3 Cl + NaOH CH3OH + NaCl (SN: th nucleophin)

Tng qut:
R-X + Y R- Y + X
( X: nhm b th, Y: nhm th )
1.1.2.2. Phn ng cng (A: Addition)
Phn ng kt hp mt hay nhiu nhm th vo phn t cha no.
Phn ng thng xy ra trong cc hp cht c ni i, ni ba.
V d:
CH3 - CH = CH2 + HCl CH3 - CHCl - CH3 (AE)
CH3 - CH = O + HCN CH3 - CH(CN) - OH (AN)
peroxit
CH3 - CH = CH2 + HBr CH3 - CH2 - CH2Br (AR)

1.1.2.3. Phn ng tch (E: Elimination)
Phn ng loi mt hay nhiu nhm nguyn t ra khi phn t
V d:
H2 SO4
CH3 - CH2OH CH2 = CH2 + H2O
1800 C
kim/ru
CH3 - CHCl - CH3 CH3 - CH = CH2 + HCl
1.2. Bn cht lin kt trong Ho hu c
C nhiu loi lin kt nhng trong Ho hu c lin kt quan trng nht l
lin kt cng ho tr.
Theo quan im hin i lin kt cng ho tr c hnh thnh do s xen ph
cc orbital nguyn t (AO), orbital nhn c gi l orbital phn t (MO). Tu vo
s xen ph ngi ta phn bit 2 loi lin kt sau:
1.2.1. Lin kt (xen ph trc)
Lin kt ny c hnh thnh do s xen ph cc i ca cc cp orbital: s-s, s-p,
p-p.Trc i xng trng vi ng thng ni lin vi 2 ht nhn nguyn t.
M t:
s - s s - p p - p
Cc orbital p dng lai ho c hnh qu t i khng cn i.
c im:
- Lin kt tng i bn, do vy cc cht c cu to bi ch lin kt ny
iu kin thng kh tr v mt ho hc.
- Cc nhm th ni vi nhau bng lin kt c th quay quanh trc lin kt.
1.2.2. Lin kt (xen ph bn)
Lin kt ny c hnh thnh do s xen ph tng phn ca cc cp orbital: p-
p, p-d, d-d. Trc i xng c th song song hoc ct nhau.
M t:
Cc orbital p dng cha lai ho c hnh qu t i cn i.

c im:
- Lin kt km bn
- Cc nhm th ni nhau bng lin kt khng th quay t do c
1.3. Cu trc phn t hp cht hu c
Thuyt cu to ho hc ca ButLeRop ra i gii quyt c rt nhiu
vn trong ni bc nht l hin tng ng phn.
C 2 loi ng phn:
1.3.1. ng phn cu to (mt phng)
- ng phn mch C
- ng phn nhm chc
- ng phn v tr nhm chc
- ng phn lin kt
u nhc im ca ng phn cu to
u im: phn nh c cu to ca cht t cho php d on c tnh
cht c trng ca cht .
V d:
C2H5-OH: c H linh ng
C2H6O
CH3-O-CH3: khng c H linh ng
Nhc im: Cha phn nh c cu to thc s (cu trc) ca cc cht, t
cha gii thch c mt vi hin tng thc t.
1.3.2. ng phn khng gian (lp th)
1.3.2.1. Thuyt t din ca C
Van Hop v L Ben tm ra cu trc c bit ca C (nm 1874), hai ng
a ra thuyt t din ca C.
Ni dung:
"Trong hp cht hu c 4 ho tr ca C hng ra 4 nh ca mt hnh t
din, cc gc tm u bng nhau v bng 1090 28' ".
M t: a
1090 28
C
b 0
109 28
d
c
C 2 loi ng phn khng gian:

1.3.2.2. ng phn hnh hc
1. nh ngha: l loi ng phn gy nn do s phn b khc nhau trong khng gian
ca cc nhm th xung quanh mt b phn c nh (ni i, vng no)
a. Trng hp ni i
Phn t c 1 ni i s c 2 ng phn hnh hc c gi l cis v trans (nu
ni i l C=C), gi l syn v anti (nu ni i l C = N hay N = N).
Hai nhm th ging nhau nm cng pha i vi ni i th gi l ng
phn dng cis hay syn.
Ngc li nm khc pha th gi l trans hay anti.
H H H COOH
C C C C
HOOC COOH HOOC H
dng cis dng trans
C6 H5 C6 H5 C6 H5
N N N N
dng syn dng anti C6 H5
b. Trng hp vng no: cng tng t
OH
OH
OH
OH
dng cis dng trans
2. iu kin c ng phn hnh hc
- Phn t phi c ni i hay vng no.
- Hai nhm th gn vi mi C ca ni i hay vng no phi khc nhau.
1.3.2.3. ng phn quang hc
1. nh ngha:
Nhng ng phn c tnh cht l, ho ging nhau ch khc nhau v kh nng
lm quay mt phng phn cc ca nh sng phn cc gi l ng phn quang hc
ca nhau.
Cht lm quay mt phng phn cc gi l cht quang hot.
mt phng b lch
cht hot quang
as phn cc
nicol
as t nhin
Khi cho nh sng phn cc i qua cht hot quang mt phng dao ng ca
nh sng b lch i mt gc ( : gc quay cc) c o bng my phn cc k.
Cht lm quay mt phng sang tri ( < 0) gi l cht quay tri
Cht lm quay mt phng sang phi ( > 0) gi l cht quay phi
Khi trn 50% ng phn quay tri vi 50% ng phn quay phi ta thu c
hn hp gi l bin th racemic
2. iu kin c ng phn quang hc
iu kin c bn l phn t phi c cu hnh bt i xng, mt trong nhng
yu t to nn s bt i ca phn t l s xut hin ca nguyn t C bt i, k
hiu: C*.
C*: 4 ho tr ca C lin kt vi 4 nhm th khc nhau.
a
C*
b d
Phn t c 1C* th s c 2 cu hnh ging nhau nhng khng th chng kht

ln nhau c m ch i xng nhau qua gng phng. Hai cu hnh nh vy gi l
2 ng phn quang hc ca nhau (1 cp i quang).
Khi s C* tng th s ng phn quang hc tng nhanh
S ng phn quang hc c tnh:
N = 2n
Trong : n: s C*
N: s ng phn quang hc
i vi trng hp phn t c 1C* th vic biu din cu hnh di dng t
din d dng nhng phn t c t 2C* tr ln th vic biu din kh khn. Do vy
n gin khi biu din ngi ta dng cng thc chiu Fischer.
Cng thc Fischer l hnh chiu ca cng thc t din ln mt phng tho
mn cc quy c:
- ng thng ng ng vi 2 lin kt hng xa theo hng nhn
- ng nm ngang ng vi 2 lin kt gn theo hng nhn.
Lu :
Nhm c bc oxi ha ca C cao c t nm trn, nhm c bc oxi ha
thphn c t nm di ng thng ng.
Bc oxi ho ca C: - COOH > - CHO (-CO-) > - CH2OH > - R
a
a
c d
b C
d
c b
a a
a
c b
C C
c c c b
b b
a
3. Cc v d c th
V d 1:
Xt phn t axit lactic CH3 - C*HOH - COOH
Phn t c 1C* c 2 ng phn quang hc (1cp i quang)
COOH COOH
H OH HO H
CH3 CH3
V d 2:
Xt phn t C6H5 - C*H(NH2)-C*H(NH2)-COOH
axit 2,3-diamino - 3phenyl propanoic
Phn t c 2C* c 4 ng phn quang hc (2 cp i quang)
COOH COOH COOH COOH
H NH2 H2N H H NH2 H2N
H
H NH2 H2N H H2N H H NH2
C6H5 C6H5 C6H5 C6H5
4. Danh php D,L

sp xp cc cht hot quang theo dng D hay L chn cu hnh glyxeraldehyt
lm chun.
CHO CHO
H OH HO H
CH2 OH CH2OH
D (+) glyxeral L(-) glyxeral
(+): ch cht lm quay mt phng sang phi
(-): ch cht lm quay mt phng sang tri
- Nu phn t ch c 1C*
Chng hn:
Hp cht R - C*HX - R' vi X (halogen, - OH, - NH 2 ...)
Tu v tr X bn phi hay bn tri C* m ta c cu hnh D hay L.
R R
H X X H
R' R'
dng D dng L
- Nu phn t c nhiu C* ta chn cu hnh C* xa nhm chc nht.
CHO CHO
H OH HO H
HO H H OH
H OH HO H
H OH HO H
CH2 OH CH2 OH
D (+) glucose L (-) glucose

1.4. Hiu ng ho hc
Cc nhm th trong phn t c nh hng qua li ln nhau c th trc tip hoc
gin tip. S nh hng qua li dn n lm thay i s phn cc ca cc lin
kt trong phn t. nh hng nh vy ca cc nhm th gi l hiu ng ho hc.
Cc loi hiu ng thng gp.
1.4.1. Hiu ng cm ng (I)
1.4.1.1. Khi nim
3
Xt phn t: CH3 - 2CH2 - 1CH2 Cl
Lin kt 1C Cl phn cc (do Cl c m in ln hn C) lm cho cc lin
kt 2C 1C 3C2 C cng phn cc theo tuy mc yu dn. Ta ni Cl gy hiu
ng cm ng.
Hiu ng cm ng biu din bng mi tn thng
nh ngha: Hiu ng cm ng sinh ra do s dch chuyn mt e gy
nn do s chnh lch m in.
1.4.1.2. Quy lut
- H khng ht, khng y e (I = 0)
- Nhm th ht e mnh hn H gy hiu ng cm m (-I).
m in cng ln, nhm cng cha no gy hiu ng - I cng mnh.
- F > - Cl > - Br > - I
-I - F > - OH > - NH2
- C CH > - CH = CH2
Mt s nhm th khc gy hiu ng I: - OR, - CN, - NO2, SO3 H ......
- Nhm th y e mnh hn H gy hiu ng cm dng (+I).
Cc nhm gy +I l gc ankyl, gc cng phc tp gy hiu ng cng mnh.
CH3)3C - > (CH3)2CH-CH2 - > (CH3)2CH - > C 2H5 - > CH3 -
1.4.1.3. c im - ngha
- Hiu ng I ch truyn theo mch v gim nhanh cng khi mch
ko di.
C - C - C Cl 1 (+) > 2 (+) > 3 (+)
- Hiu ng I gip ta gii thch tnh axit, baz v kh nng phn ng ca

cc cht.
Cc nhm th gy +I lm gim tnh axit, tng tnh baz v ngc li cc
nhm th gy -I lm tng tnh axit, gim tnh baz.
Chng hn:
Tnh axit: CH2Cl - COOH > CH3 - COOH
-I +I
Tnh baz: CH3 - NH2 > O2 N - CH2 - NH2
+I -I
1.4.2. Hiu ng lin hp (C)
1.4.2.1. Khi nim
* H lin hp
- H lin hp - : h cha lin kt i xen k lin kt n.
- H lin hp p - : h cha nguyn t cn cp e cha chia lin kt vi C
mang ni i.
CH2 = CH - CH = CH2

Cl - CH = CH2 OH
p- p-
Xt phn t c h lin hp:
5
CH2 = 4CH - 3CH = 2 CH - 1CH = O
Lin kt C = O phn cc v pha O, 1C = O phn cc dn n lin kt 3 C =
2
C cng b phn cc v 2 C, lin kt 5C = 4C tng t.
CH2 = CH - CH = CH - CH = O
Ta ni nhm - CHO gy hiu ng lin hp.
Hiu ng lin hp c biu din bng mi tn cong i t lin kt i n
lin kt n hoc t i in t cha chia n lin kt n theo h.
nh ngha: Hiu ng dch chuyn e trong h lin hp gy ra do s chnh
lch m in gi l hiu ng lin hp.
Nhm ht e gy hiu ng lin hp m (-C)
- NO2, - CHO, - COOH, - CN ...(cc nhm khng no)
Nhm y e gy hiu ng cm dng (+C)
- OH, - OR, - NH2, halogen ... (cc nhm c i e cha chia)
Lu : Mt s nhm c hiu ng C vi du khng c nh nh vinyl,
phenyl ...
O
N NH 2
O
+C -C -C +C
1.4.2.2. Quy lut
- m in nguyn t cng ln - C cng ln.
- C: - CO - > - C = N - > - C = C -
- Trong 1 phn nhm +C gim t trn xung
- Trong 1 chu k +C gim t tri sang phi
- F > - Cl > - Br > - I
+C
- NH2 > - OH > - F
1.4.2.3. c im
- Hiu ng C ch lan truyn theo h lin hp phng.
- t thay i khi mch ko di
Ch :
1. Hiu ng do nhm th gy ra cn tu thuc vo nhm m n ni.
10
O2N - CH2 - CH2 - COOH (NO2: - I)
O2N COOH (NO2: -I, -C)
CH2 = CH - O - CH3 (CH2 = CH - : -C)
CH2 = CH - C N (CH2 = CH - : +C)
2. Trong phn t thng gp cc nhm th c c 2 loi hiu ng I, C.
+ Khi I v C cng du tng cng tc dng
Chng hn: - NO2 , - SO3H .....
Chng hn:
O
-N (-I, -C): ht e mnh
O
+ Khi I v C ngc du gim tc dng ca nhau hiu ng tng qut.
- NH2, - OH, - OR c + C > - I hiu ng tng qut l y e.
c bit cc nguyn t halogen c I > + C do vy hiu ng tng qut l ht e.
Tm li hai loi hiu ng trn u c dng gii thch tnh cht ca cc
cht v kh nng phn ng ca chng.
11
CHNG II. HYDROCACBON
Hydrocacbon l hp cht hu c m thnh phn phn t ch gm 2 nguyn t l C v H.

Tu vo kh nng lin kt v tnh cht ca chng ngi ta chia lm 3 loi:
Hydrocacbon
Hydrocacbon no Hydrocacbon cha no Hydrocacbon thm
ankan xycloankan ankan ankadien ankyn aren

2.1. Hydrocacbon no
2.1.1. Ankan
2.1.1.1. Khi nim - Danh php
1. Khi nim: Ankan l loi hydrocacbon mch h trong phn t ch gm cc lin kt .
Cng thc tng qut: Cn H2n + 2
2. Danh php
Bn cht u c tn gi ngu nhin tu theo mun ca ngi tm ra chng.
CH4 : metan C3 H8 : propan
C2 H6 : etan C4 H10 : butan
T C5 H12 tr i tn gi c quy lut:
Tn cc ch s Hylap + an
C5 H12 : pentan C8 H18 : octan
C6 H14 : hexan C9 H20 : nonan
C7 H16 : heptan C10 H22 : decan
l tn gi cc cht trong trng hp mch C thng, khi mch C phn nhnh tc xut
hin ng phn tn gi ca chng phc tp hn. thng nht ngi ta a ra danh php
chung gi l danh php IUPAC. gi tn theo danh php ny ngi ta thc hin cc bc
sau:
- Chn mch C di nht lm mch chnh
- nh s mch chnh: theo quy tc tng s nhnh b nht
- Gi tn: V tr nhnh + s nhnh + tn nhnh + tn mch chnh
Ch : Khi gi tn cc nhnh gi theo th t alphabet (nu c nhiu nhm th khc nhau)
Mt s nhnh thng gp:
- CH3 : metyl, - C2 H5 : etyl, - CH2 - CH2 - CH3 : n-propyl, - CH(CH3 )2 : isopropyl
11
CH3 - CH(CH3 ) - CH(CH3 ) - CH2 - CH3 2,3-dimetyl pentan
CH3 - CH(CH3 ) - CH - CH2 - CH3 3-etyl-2-metyl pentan
CH3 -CH2
2.1.1.2. L tnh
Bn cht u th kh do lc ni cc phn t yu, cc cht sau th lng v th rn, t0 s
v t0 nc tng theo ch s C do lc lin kt phn t mnh.
Tt c chng u l nhng cht khng mu, khng mi, t tan trong nc, d tan trong
cc dung mi khng phn cc hoc km phn cc.
2.1.1.3. iu ch
1. Hydro ho anken: Cho anken tc dng vi H2 c Ni xc tc

Cn H2n + H2 Cn H2n+2
2. i t mui axit hu c: Cho mui tc dng vi NaOH co mt CaO

RCOONa + NaOH RH + Na2 CO3
3. Phng php ghp mch (Wurts - Fittig)

Cho dn xut monohalogen tc dng vi Na trong mi trng ete khan.
2R - X + 2 Na R - R + 2NaX
Phng php ny thng dng iu ch cc ankan c tnh cht i xng.
2.1.1.4. Ho tnh
Do phn t bn nn iu kin thng ankan kh tr v mt ho hc. Khi c iu kin:
(t0 cao, bc x, as ... ) ankan cng tham gia phn ng v phn ng c trng l phn ng th.
1. Phn ng th
Cc H ca ankan c th dn bi cc tc nhn th.
Tc nhn th: halogen (X2 ), HNO3 l, H2 SO4 l ...
Tn phn ng: halogen ho, nitro ho, sunfo ho ...
a. Phn ng halogen
R- H + X2 R- X + HX
Kh nng phn ng:
gim dn
F2 I2
Tc nhn halogen ho thng gp: Cl2 , Br2 , xc tc: nh sng, nhit ....
Xt phn ng c th: CH4 phn ng vi Cl2
CH3 Cl: metyl clorua
CH4 + Cl2 as CH2 Cl2 : metylen clorua
- HCl CHCl3 : clorofoc
CCl4 : cacbontetraclorua
12
C ch phn ng: xy ra theo c ch gc t do (SR) gm 3 giai on:
Giai on 1: giai on khi u
as
Cl2 2Cl
Giai on 2: giai on pht trin mch

CH4 + Cl CH3 + HCl

CH3 + Cl2 CH3 Cl + Cl

CH3 Cl + Cl CH2 Cl + HCl

CH2 Cl + Cl2 CH2 Cl2 + Cl
Phn ng c tip tc xy ra cho n khi to thnh sn phm cui cng (phn ng dy chuyn)
Giai on 3: giai on tt mch
Xy ra khi cc gc t do kt hp vi nhau to phn t bn

Cl + Cl Cl2

CH3 + Cl CH3 Cl
Quy tt th: Phn ng xy ra u tin th H nguyn t C bc cao.
as
CH3 -CH-CH2-CH3 + Br2 CH3 -CBr - CH2 - CH3 + HBr
CH3 CH3
b. Phn ng nitro ho:tng t phn ng halogen ho v c ch cng nh quy tc th.
H2 SO4
R - H + HO - NO2 R - NO2 + H2 O
t0
2. Phn ng hu: t0 cao khng c O2KK cc ankan b phn hu b gy mch C to thnh

nhng hydrocacbon c mch ngn hn. Qu trnh ny gi l qu trnh cracking.
CnH2n+2 Cx H2x+2 + Cy H2y
( x, y < n )
Qu trnh cracking c s dng nhiu trong k ngh ch bin du m.
3. Phn ng oxi ho
- Oxi ho hon ton: sn phm l CO2 , H2 O
- Oxi ho khng hon ton: tu iu kin cho sn phm khc nhau.
+ i vi CH4
200at, 3000 C,
H - CHO + H2 O
0
500 C, Ni
CH4 + O2KK CO2 + H2
thiu kkh
C + H2 O
13
+ i vi cc ankan khc: oxi ho km theo s b gy mch C.
[o]
R-CH2 -CH2 -R' R - COOH + R - COOH
Cht tiu biu: CH4
CH4 : l cht kh c nhiu trong t nhin: hm m, m ao do s phn hy xenlulo di
tc dng ca vi khun ym kh.
v.k.y.k
(C6 H10O5 )n + nH2 O 3nCH4 3nCO2
CH4 c dng lm nguyn liu tng hp cc cht hu c: CH3 OH, HCHO, C2 H2 v
cc dn xut halogen.
2.1.2. Xycloankan
Xycloankan l loi hydrocacbon mch vng, no.
Cng thc tng qut: Cn H2n (n 3)
Xycloankan c gi tn nh ankan ch thm tip u ng l xyclo (vng)
xyclopropan xyclohexan
Xycloankan ngoi cc loi ng phn thng thng cn c ng phn hnh hc (ng
phn cis-trans) v ng phn quang hc, trong ng phn hnh hc ph bin nht.
2.1.2.2. bn v cu to lp th cc vng.
Nm 1885 Baeyer a ra gi thuyt sc cng vng gii thch bn vng. Theo ng
gc lin kt C no bnh thng l 1090 28' cn gc lin kt gia cc C trong vng tu thuc s
cnh vng (3 cnh: 600 , 4 cnh: 900 , 6 cnh: 1200 ...) S sai khc gia cc vng ny vi 1090 28'
gy nn sc cng vng, sai khc cng ln th sc cng cng ln v vng cng km bn.
Vng 3,4 cnh: km bn
Vng 5,6 cnh: bn hn
Cu to lp th cc vng.
- Vng 3 cnh: cu to phng - Vng 5 cnh: dng na gh
- Vng 4 cnh: cu to gy gp - Vng 6 cnh: dng gh, dng thuyn
Thng gp nht l vng 6 cnh, dng bn ca vng 6 cnh l dng gh.
dng gh (99,9%)
14
2.1.2.3. Ho tnh
Vng 3, 4 cnh km bn nn tnh cht ging anken phn ng c trng l phn ng
cng.
+H2
CH3 - CH2 - CH3
0
Ni, t
+Br2
CH2 Br - CH2 - CH2 Br
Vng 6 cnh bn nn tnh cht ging ankan phn ng c trng l phn ng th.
xc tc Cl
+ Cl2 + HCl
2.2. Hydrocacbon cha no

2.2.1. Anken
- Anken l loi hydrocacbon cha no trong phn t c cha 1 lin kt i (1 lin kt
va 1 lin kt )
Cng thc tng qut: Cn H2n (n 2)
- Danh php: i ui an thnh en km theo v tr ni i
CH2 = CH2 : eten (etylen)
CH3 - CH = CH - CH3 : 2-butten
CH3 - C(CH3 ) = CH - CH3 : 2-metyl-2-buten
Cc gc thng gp:
CH2 = CH - : etenyl (vinyl)
CH3 - CH = CH -: propenyl-1
CH2 = CH - CH2 - : propenyl-2 (allyl)
2.2.1.2. iu ch
1. i t dn xut monohalogen
Cho dn xut i qua mi trng kim/ru
K/R
R - CH2 - CHX - R' R - CH = CH - R'
-HX
Phn ng tun theo quy tc Zay Xep (tch H C bc cao)
2. i t dn xut dihalogen
Cho dn xut tc dng vi bt Zn c mt xc tc CH3 COOH
x/t
R - CHX - CHX - R' + Zn R - CH = CH - R' + ZnX2
15
3. i t ancol
un hn hp ancol vi H2 SO4 t0 1700C
H+, 1800 C
R - CH2 - CHOH - R' R - CH = CH - R' + H2 O
2.2.1.3. Ho tnh

C C

Lin kt km bn nn d b b gy.
Do vy phn ng c trng ca anken l phn ng cng.
1. Phn ng cng
Phn ng
C=C + X+ - Y- CX - CY
C ch: cng elctronphin (AE)
Phn ng xy ra qua 2 giai on
chm
C=C + X+ C - C+
X
nhanh
C - C+ + Y- C-C
X X Y
Tc nhn: X2 (halogen), HX, H2 O ...
Minh ho bng mt s phn ng:
CCl4
CH2 = CH2 + Br2 CH2 Br - CH2 Br
nu khng mu
CH3 - CH = CH2 + HCl CH3 - CHCl - CH3
CH3 - CH(CH3 ) - CH = CH2 + H2 O CH3 - CHOH - CH(CH3 ) - CH3
(Qui tc Maccopnhicop)
+HBr
CH3 - CHBr - CH3 (1) AE
CH3 - CH = CH2
+HBr
CH3 - CH2 - CH2 Br (2) AR
peroxit
(1) : phn ng tun theo qui tc Maccopnhicop

(2) : phn ng ngc vi qui tc Maccopnhicop
16
2. Phn ng oxi ho
Tu iu kin v tc nhn m cho sn phm khc nhau
a. Tc nhn oxi ho yu: sn phm l -diol
R - CH = CH - R' + KMnO4 + H2 O R - CH - CH - R ' + MnO2 + KOH
OH OH
-diol
Phn ng ny chng minh anken lm mt mu thuc tm long.
b. Tc nhn oxi ho mnh: tu mc m to thnh hp cht cacbonyl hay axit cacboxylic.
* Vi O3 (phn ng ozon phn):
Sn phm l hp cht cacbonyl
R' H2 O
R - CH = C + O3 R - CHO + R' - CO - R'' + H2 O2
+
R'' H
Mc ch phn ng ny dng xc nh v tr lin kt i trong hp cht u.

* Vi KMnO4 : sn phm c th l axit hoc xeton tu cu to cht u.
R'
t0
R - CH = C + KMnO4 R - COOK + R' -CO - R'' + MnO2 + H2 O + KOH
R''
3. Phn ng trng hp t0 , p, x/t
nR - CH = CH - R' (- CHR CHR -)n
Phn ng ny c dng iu ch cht do, cao su, nha ...
Cht tiu biu: C2 H4
C2 H4 l cht kh khng mu, khng mi, khng v, t tan trong nc, c tc dng kch
thch s hot ng ca enzym lm qu mau chn.
C2 H4 cn c dng iu ch ru etylic, y l hp cht rt quan trng trong cng
nghip v c trong i sng.
2.2.2. Ankadien
Ankadien l loi hydrocacbon cha no c cha 2 lin kt i trong phn t.
C 3 loi:
- Hai ni i lin nhau: CH2 = C = CH2 propadien
- Hai ni i cch xa nhau: CH2 = CH - CH2 - CH = CH2 1,4 - pentadien
- Hai ni i xen k nhau (ankadien lin hp): y l loi c ngha nht chng hn:
CH2 = CH - CH = CH2 1,3 - butadien
CH2 = C(CH3 ) CH = CH2 2- metyl 1,3 - butadien
17
2.2.2.2.Ho tnh
Cc ankadien lin hp c tnh cht tng t anken tuy nhin do c n hai ni i nn
hot tnh mnh hn ng thi do xut hin hiu ng lin hp nn nh hng nhiu n tnh
cht ca n cng nh cc dn xut ca n.
Phn ng c trng cng l phn ng cng.
1. Phn ng cng: cho 2 phm vt cng tu iu kin, iu kin quyt nh nht l nhit .
- Nhit thp: cho phm vt cng 1-2
- Nhit cao: cho phm vt cng 1-4
CH2 Br - CHBr - CH = CH2
+Br2 t0 , thp
CH2 = CH - CH = CH2 t0 , cao
CHBr - CH = CH - CH2 Br
2. Phn ng trng hp
t0 , p, x/t
n CH2 = CH - CH = CH2 (- CH2 - CH = CH - CH2 -)n
cao su Buna
2.2.2.3. Hp cht c nhiu ni i
1. Tecpen: l loi hydrocacbon t nhin c cng thc tng qut l: (C5 H8 )n vi n 2, tecpen c
nhiu tinh du thc vt.
Chng hn tinh du myxen cy nguyt qu.
CH3 - C = CH - CH2 - CH2 - C = CH2
CH3 CH = CH2
Dn xut ca tecpen gi l tecpenoit cng c trong tinh du thc vt (cnh hoa hng,
hoa bi, v cam chanh, l s ...)
CH3 - C = CH - CH2 - CH2 - C = CH - CH2OH (tinh du hoa hng)

CH3 CH3
2. Caroten:
Caroten l nhng sc t t nhin thng c mu vng, da cam, xut hin cc loi
qu nh: c chua, c rt, gc ... phn t cha mt lot cc lin kt i xen k lin kt n tc
c cha nhm -C = C - (nhm mang mu)
C 3 loi caroten: , , caroten
Cu to caroten:
CH3 CH3 CH3 CH3
CH CH C CH CH ..... CH =C CH CH
CH3 CH3
CH3 CH3
vng ionon (mch thng cha 18C)
18
caroten khi b thu phn cho 2 phn t vitamin A
C H3 C H3
H2 O CH CH C CH CH CH
caroten
C H3 C H3 C CH3
carotenase
CH
vitamine A CH2OH
v caroten khi b thu phn cng cho vitamin A nhng hm lng t hn (ch 1
phn t)
Vitamin A c nhiu cng dng:
- Cha bnh qung g, kh mt
- To sc t th gic gip ngi v ng vt nhn c trong bng ti.
S tng hp Rodopsin:
Rodopsin
Opsin
cis Retinal trans Retinal

NADH, H+ NADH, H+
NAD+ NAD+
enzyme
cis Retinol trans Retinol
Rodopsin: sc t th gic
Opsin: protein
Retinol: vitamin A
Thiu vitamin A gy bnh l nhng tha vitamin A cng gy nguy him: bnh thn
kinh (m sng, lon tm thn), kh da, nt mi, gim bch hu ...
2.2.3. Ankyn
- Ankyn l hydrocacbon cha no trong phn t c cha 1 lin kt ba
Cng thc tng qut: Cn H2n-2 (n 2)
- Danh php: i ui an thnh yn km theo v tr ni ba
CH CH: etyn (axetylen)
CH3 - CH2 - C CH: 1-butyn
19
2.2.3.2. iu ch
1. T dn xut dihalogen
Cho dn xut i qua mi trng kim/ru
R - CHX - CHX - R'
R - C C - R' + 2HX
R - CH2 - CX2 - R'
2. T dn xut tetra halogen
Cho dn xut tc dng vi bt Zn c mt xc tc CH3 COOH
xc tc
R - CX2 - CX2 - R' + 2Zn R - C C - R' + 2ZnX2
3. Thu phn CaC2 (iu ch C2 H2 )
CaC2 + 2H2O Ca(OH)2 + C2 H2
2.2.3.3. Ho tnh
Cng nh anken l mt hydrocacbon cha no nn phn ng c trng l phn ng cng.
1 lin kt : bn
- C C - 2 lin kt : km bn
1. Phn ng cng
Xy ra qua 2 giai on: - Chuyn ni ba thnh i
- Chuyn ni i thnh n
Tu iu kin m sn phm cng c th no hay cha no (tc cng t l 1: 1 hay 1: 2)
Pd
CH CH + H2 CH2 = CH2
Ni
CH CH + 2H2 CH3 - CH3
CH2 = CHCl (1:1)
CH CH + HCl
CH3 - CHCl2 (1:2)
c bit khi cho ankyn tc dng vi H2O th ch ring C2 H2 cho sn phm l andehyt
cn cc ankyn khc cho sn phm l xeton.
ch. v
Hg 2+
CH CH + H2 O [CH2 = CH] CH3 - CHO
OH
2+ ch. v
Hg
R - C C - R' + H2 O [R - C = CH - R'] R - CO - CH2 - R'
OH
20
2. Phn ng oxi ho
Do c n 2 lin kt km bn nn qu trnh oxi ho xy ra mnh hn b gy c ni ba,
sn phm thu c a phn l axit cacboxylic.
[O]
R - C C - R' R - COOH + R' - COOH
CH3 - C C - CH3 [O] 2CH3 - COOH
c bit cc ankyn c ni ba u mch (cn H linh ng) c th tham gia phn ng th.
3. Phn ng th
Cc ankyn c ni ba u mch gi l ankyn -1.
C2 H2 v cc ankyn -1 c th th H ca ni ba bi kim loi hay ion kim loi.
Chng hn: t0
R - C CH + Na R - C C Na + 1/2H2
R - C CH + NaNH2 R - C CNa + NH3
R - C CH + Ag(NH3 )2 OH R - C CAg vng nht + NH3 + H2 O
R - C CH + Cu (NH3 )2 Cl R - C CCu gch + NH3 + H2 O
Phn ng ny c dng nhn bit ankyn -1.
4. Phn ng trng hp
Xt trng hp in hnh l C2 H2
Tu iu kin m xy ra cc kiu trng hp khc nhau: trng hp vng, trng hp
thng hay to polime.
Kh nng trng hp vng thng xy ra nht v y l phng php iu ch
benzen.
600 8000 C, C
3C2 H2 C6 H6
Cht tiu biu: C2 H2
C2 H2 l cht kh khng mu khi chy to ngn la mu xanh rt sng to nhit ln v
vy c dng hn v ct kim loi (cc loi n x).
C2 H2 c dng iu ch cc ho cht cn thit khc: andehyt, axit, mt s nha
quan trng: P.V.C, P.V.A ...
C tc dng kch thch s sinh trng ca cy trng nht l kch thch s ra hoa, kt qu,
lm qu mau chn.
2.3. Hydrocacbon thm
2.3.1. Khi nim - Phn loi
Hydrocacbon thm l loi hydrocacbon c cha vng benzen trong phn t.
Cng thc tng qut: Cn H2n-6 (n 6)
Da vo cu to ngi ta chia lm 2 loi chnh:
21
- Hydrocacbon thm mt nhn (n vng)
- Hydrocacbon thm nhiu nhn (a vng)
Trong phn ny chng ta ch yu kho st loi mt nhn, loi ny kh nng phn ng
mnh cng nh ng dng thc t nhiu hn.
Tt c hydrocacbon thm u c vng benzen, do vy trc ht chng ta xt cu to
ca vng benzen.
2.3.2. Cu to benzen
Cng thc phn t benzen: C6 H6
* Cu to ca KeKuLe (c in):
u im: m bo ho tr cc nguyn t
Nhc im:
- d C - C > d C = C, nh vy khong cch C - C trong benzen phi khc nhau nhng
thc t chng li bng nhau.
- Phn t c n 3 lin kt i ng l phn ng c trng l phn ng cng nhng thc
t phn ng c trng li l phn ng th.
* Cu to theo quan im hin i
Theo quan im hin i C trong benzen c lai ho sp2 mi C cn 1 orbital p thun tu
cha lai ho, 6 orbital ny xen ph ln nhau to h thng lin kt bn vng gi l h lin hp
thm bn vng.
Do h thm bn nn phn ng c trng ca benzen l phn ng th. Trong h thm
mt e dn u trn tt c cc lin kt do vy khong cch C - C u nh nhau.
Cu to benzen c th c biu din:
hay
2.3.3. Danh php - V tr cc nhm th

Cc ng ng ca benzen c xem l dn xut ca benzen do vy tn gi chng c
gi theo benzen.
22
CH3 CH(CH3)2
metyl benzen isopropyl

(toluen) benzen
(cumen)
Trng hp phn t c nhiu nhm th ngi ta tin hnh nh s th t 6 nh ca
vng bt u t nh no gn vi nhm th n gin nht.
CH3 CH3
1 1
2 2
6 CH3 6
5 3 5 3 C2 H5
4 4
1,2 - dimetyl benzen 1,3 -dimetylbenzen

(o. xylen) (m. xylen)
V tr (2) (6):v tr octo (o), v tr (3) (5: v tr meta (m),v tr (4): v tr para (p)
2.3.4. iu ch:
Nha than l ngun nguyn liu ch yu v quan trng cung cp hydrocacbon thm.
Ngoi ra c th iu ch hydrocacbon thm bng phng php ha hc.
Cho ben zen tc dng vi ankylhalogenua c mt xc tc AlCl3
AlCl3
C6 H6 + R- X C6 H5 - R + HX
2.3.5. Ho tnh
Do h thm bn vng nn phn ng c trng ca aren l phn ng th, phn ng cng
v oxi ho xy ra kh khn hn
2.3.5.1. Phn ng th
Phn ng tng qut:
xc tc
Ar - H + X- Y Ar - X + H - Y
C ch: xy ra theo c ch th electronphin (SE) phn t tn cng u tin vo aren l
tc nhn electronphin. Gm 2 giai on:
R
R + X X
X X
H H Y- + HY
+
phc phc
(km bn)
giai on 1 giai on 2
23
Cc phn ng thng gp (ly benzen minh ho):
+ X2 X + HX :halogen
bt st ho
+ HNO3 l NO2
H2 SO4 l + H2 O : nitro ho
+RX
R + HX : ankyl ho
AlCl3
+ R - CO - X
CO-R
AlCl3
+ HX : axyl ho
Kh nng phn ng ph thuc vo cc nhm th c trn nhn.

- Nhm trn nhn y e hot ho nhn kh nng phn ng tng.
- Nhm trn nhn ht e gim hot kh nng phn ng gim.
Lu : i vi cc ng ng ca benzen phn ng c th xy ra theo 2 khuynh hng tu
iu kin.
- Th vo nhn: nu xc tc to tc nhn electronphin (c ch SE)
+ Nhm y e nh hng nhm th mi vo v tr o v p
+ Nhm ht e nh hng nhm th mi vo v tr m
- Th vo nhnh: nu iu kin to gc t do (c ch SR)
2.3.5.2. Phn ng cng: xy ra kh khn hn cn iu kin c bit.
Cl
Cl Cl
as
+ 3Cl2
Cl
Cl
Cl
(un si)
hexacloxyclohexan
Sn phm to thnh c 8 ng phn hnh hc, trong 8 ng phn ch c ng phn

(14%) c tnh c dc c dng lm thuc tr su (6.6.6.)
2.3.5.3. Phn ng oxi ho
Do vng bn nn kh b oxi ho, di tc dng ca cht oxi ho vng hu nh khng b ph v.
Tuy nhin cc ng ng ca benzen th vn b oxi ho phn nhnh, phn ng xy ra
lm t mch C v ch li trn nhn 1C duy nht.
KMnO4
C6 H5 - CH2 - CH2 - CH3 C6 H5 - COOH + CH3 - COOH
24
25
CHNG III. DN XUT HALOGEN ANCOL PHENOL
3.1. Dn xut halogen

Dn xut halogen l hp cht thu c khi thay th mt hay nhiu nguyn t
H bng nguyn t halogen (X).
Dn xut halogen c phn loi da vo 2 yu t:
Gc R S nguyn t halogen
Dn xut no, cha no, thm Dn xut mono, di,
polihalogen
Quan trng nht l dn xut monohalogen no
3.1.1. Danh php
Cng thc tng qut:
CnH2n+1 X hay R - X (R: gc ankyl)
- Tn thng: tn gc ankyl + halogenua
CH3Cl: metylclorua
CH3- CH-Br: isopropylbromua
CH3
- Tn quc t: v tr + tn halogen + tn ankan
CH3 - CH - Br : 2-brompropan
CH3
Cl
CH3 - C - CH3 : 2-Clo-2-metylpropan
CH3
3.1.2. iu ch
3.1.2.1. Halogen ho ankan as
R - H + X2 R - X + HX
(Ch quy tc th)
3.1.2.2. Cng hp HX vo anken
Tu iu kin m cho sn phm khc nhau
R - CH = CH - R' + HX R - CH2 - CHX - R'
(Ch hiu ng ho hc)
25
3.1.2.3. i t ancol
Cho ancol tc dng vi cc tc nhn cha halogen
R - OH + HX R - X + H2O
R - OH + PX5 R - X + POX3 + HX
R - OH + SOX2 R- X + SO2 + HX
3.1.3. Ho tnh
R- C- X
Lin kt C - X phn cc v pha X do X c m in ln v vy phn ng
c trng ca dn xut halogen l phn ng th X bng cc tc nhn nucleophin.
3.1.3.1. Phn ng th
Phn ng tng qut:
R - X + Z + - Y- R- Y + Z- X
C ch: th nucleophin (SN)
Tc nhn tn cng u tin vo RX l Y- to thnh phc cht hot ng sau
phc ny s phn ly d to sn phm.
Y- Z+
R-X Y- .... R ..... X- R - Y + Z - X-

phc cht hot ng
Cc phn ng thng gp:
+OH-
ROH + X- : phn ng thu phn
+ NH3
R-X RNH2 + HX: phn ng to amin
+ CN-
RCN + X- : phn ng to nitrin
3.1.3.2. Phn ng loi HX
Phn ng c thc hin trong mi trng kim/ru
K/R
R - CH2 - CHX - R' R - CH = CH - R' + HX
(Ch quy tc ZayXep)
Mi trng kim: trung ho axit to thnh
Mi trng ru: trnh s thu phn ca dn xut
3.1.3.3. Phn ng to hp cht c kim
RX c kh nng tc dng vi mt s kim loi trong mi trng ete khan to
thnh dn xut c kim.
ete khan
26
R-X + Mg R - MgX (c magie)
ete khan
R-X + Zn R - ZnX (c km)
Hp cht c kim c dng iu ch axit cacboxylic v ancol cc bc.
- iu ch axit: sc CO2 vo hp cht c kim
CO2 H2 O
R - MgX RCOOMgX RCOOH +
Mg(OH)X
- iu ch ancol cc bc: cho hp cht c kim tc dng vi hp cacbonyl.
HCHO
ancol bc 1
R'CHO
R - MgX ancol bc 2
R'COR''
ancol bc 3
Ngoi dn xut monohalogen no ra cc loi dn xut khc cng c nhiu ng

dng thc t.
Mt s dn xut quan trng.
CH3Cl: Clorofoc dng lm cht gy m, st trng.
CHI3: Iodofoc dng cha vt thng, lm dung mi tch chit.
CCl4: cacbontetraclorua dng lm dung mi.
Cc hp cht ny c iu ch bng cch thc hin phn ng halogen ha
ankan.
C6H6Cl6: hexacloxyclohexan (dng lm thuc tr su) c iu ch bng
cch thc hin phn ng cng Cl2 vo benzen.
CH2Cl - CHCl - CH2 Cl: 1,2,3-triClopropan c dng iu ch glyxerin
bng cch thc hin phn ng kim ha, glyxerin l ha cht c bn dng sn
xut x phng.
D.D.T: diclodiphenyltricloetan oc iu ch bng cch cho Cloral (CCl3 -
CHO) tc dng vi Clobenzen c dung lam thuc tr su.
Cl CH Cl
CCl3
27
Hin nay loi ha cht ny b cm s dng.
CH2 = CH - Cl: vinylClorua khi trng hp to polivinylClorua mt loi
nha tt c s dng rng ri trong i sng hng ngy ca con ngi.
CH2 = CH - CH2Cl: allylClorua dng iu ch ru allylic v glyxerin
Nhn chung dn xut halogen l ho cht c bn c s dng iu ch
cc loi dn xut khc. Dn xut polihalogen l nhng cht c hot tnh ho hc vai
tr sinh hc cao c ng dng nhiu trong thc t.
3.2. Ancol
Ancol l hp cht hu c trong phn t c cha nhm - OH.
Phn loi ancol ch yu da vo gc R v s nhm - OH
Gc R S nhm - OH
ancol no, cha no, thm monoancol, poliancol
Ancol c 3 bc:
Ancol bc 1: c nhm OH nh vo C bc 1
R - CH2 OH
R
CHOH
R'
R R''
C
R' OH
Quan trng nht l monoancol no.
3.2.1. Danh php
Cng thc tng qut: CnH2n+1OH
- Tn thng: ru + tn gc ankyl + ic
- Tn quc t: v tr OH + tn ankan + ol
C2H5 - OH: etanol (ru etylic)
CH3 - CH - OH: 2- propanol (ru isopropylic)
CH3
3.2.2. iu ch - L tnh
28
3.2.2.1. Hydrat ho anken
H+
R - CH = CH - R' + H2 O R - CH2 - CHOH - R'
Phng php ny c dng iu ch cc ancol thp (C2 n C4)
Chng hn:
H+
CH2 = CH2 + H2O CH3 - CH2OH
3.2.2.2. Thu phn dn xut halogen
R- X + OH- R - OH + X-
Thng dng iu ch cc ancol c ch s cao (t C5 tr i)
C5H11 - Cl + NaOH C5H11 - OH + NaCl
3.2.2.3. Phng php Grignard: iu ch ancol cc bc
Thu phn sn phm cng ca hp cht c magie vi hp cht cacbonyl
- iu ch ancol bc 1
2)H2 O
R - MgX + 1) H - CHO H+
R - CH2 OH + Mg(OH)X
- iu ch ancol bc 2
2)H2 O
R
R - MgX + 1) R'CHO CHOH + Mg(OH)X
HH+2
R
- iu ch ancol bc 3
R R''
2)H2 O
R - MgX + 1) R'COR'' C +
Mg(OH)X H+2
H
R OH
Ancol t C1 - C10 l nhng cht lng tr tertbutylic (CH3)3C - OH l cht rn.
Cc ancol c ch s C cao l cc cht rn
Cc ancol lng l nhng cht khng mu, t0s v t0nc thng cao hn so vi
cc cht lng khc cng phn t lng do c kh nng to lin kt hydro lin phn
t.
.....OH .... OH .... OH .... OH ..... OH ....
R R R R R
Ancol tan tt trong nc mt phn cng nh to lin kt hydro vi nc
.....OH .... OH .... OH .... OH ..... OH ....
R H R H R
29
3.2.3. Ho tnh
R- C- O- H t lin kt O-H
t lin kt C-OH
3.2.3.1. Phn ng t lin kt O - H
1. Phn ng th hin tnh axit
R - OH + HOH R - O- + H3O+ Ka = 10-18
Ka rt b nn monancol no c tnh axit yu khng i mu qu tm, khng
tc dng c vi baz ch c kh nng phn ng vi cc kim loi mnh (kim,
kim th).
R - OH + K R - OK + 1/2H2
2. Phn ng este ho
Phn ng xy ra gia axit v ancol to este v nc gi l phn ng este ho
H+
R' - COOH + HO* - R R' - COO*R + H2 O
+
H
CH3COOH + HO-CH2-CH2-CH-CH3 CH3-COO-CH2-CH2-CH-CH3 +
H2O
CH3 CH3
3.2.3.2. Phn ng t lin kt C - OH
1. Phn ng to dn xut halogen
+ Cho ancol tc dng vi PX5, SOX2 un nng nh ta thu c dn xut
halogen.
R - OH + PCl5 R - Cl + POCl3 + HCl
R - OH + SOCl2 R - Cl + SO2 + HCl
+ Vi HX ch c ancol bc 2,3 phn ng to dn xut halogen
c bit: ZnCl2 khan
R - OH + HCl c R - Cl + H2O
Hn hp (HCl c + ZnCl2 khan): thuc th Lucas
thuc thLucas
Ancol bc 1 dung dch ng nht (khng
xy ra)
thuc thLucas
Ancol bc 2 dung dch c ht du vng (chm)
thuc th Lucas
Ancol bc 3 dung dch c lp du vng (nhanh)
30
2. Phn ng loi nc
C 2 kh nng:
Ancol loi nc to ete: iu kin c H2SO4 xc tc t0 < 1700C
H2 SO4
R - OH + HO - R R - O - R + H2O
0
140 C
Ancol loi nc to anken: c H2SO4 xc tc t0 1700C

H2 SO4
R CH2 CH2 OH R - CH = CH2 + H2O

0
180 C
3. Phn ng oxi ho
Nguyn t C nhm chc tch in dng cng ln th kh nng oxi ho
cng d.
Ancol bc 1 > Ancol bc 2 > Ancol bc 3
- Ancol bc 1: phn ng xy ra d dng, sn phm l andehyt hay axit
cacboxylic tu tc nhn. 0
CuO, t
R - CHO + H2O
R - CH2 OH
KMnO4
R - COOH + H2 O
H2 SO4
- Ancol bc 2: phn ng xy ra kh khn, sn phm l xeton
[O]
R CHOH - R R - CO - R' + H2O

- Ancol bc 3: rt kh b oxi ho
3.2.3.3. Phn ng halofoc
Phn ng xy ra i vi cc ancol c nhm CH3 - CH -
OH
Cc ancol c nhm ny c kh nng tc dng vi X2 / NaOH
CH3 - CH(OH) - CH3 + 4I2 + 6NaOH CHI3 vng + CH3 COONa +
5NaI + H2O
iodofoc
31
Cc cht tiu biu
1. CH3 - OH: metanol
- L cht lng khng tan trong nc, tip xc nhiu s nh hng khng tt
n c th (gy m mt, suy gim ni tng)
- Trong cng nghip metannol c iu
ZnO
CO + H2 CH3 - OH
2. C2H5 - OH: etanol
- L cht lng tan tt trong nc, c nhiu ng dng thc tin.
- Trong t nhin etanol c thc vt (qu trnh ln men ru cc loi qu)
- Trong cng nghip etanol c iu ch bng cch ln men gluxit
+ H2 O
(C6H10O5)n nC6H12O6
tinh bt enzym glucose
ln men ru
C6H12O6 2C2H5 - OH + 2CO2
3.3. Phenol.
Phenol l hp cht trong phn t c cha nhm -OH nh trc tip vo nhn
thm OH OH OH OH OH OH
CH3 OH OH
. OH OH
OH
phenol o. cresol pyrocatechin resorcin hydroquinon

pyrogalol
3.3.1. Cu to phenol
O H
Nhn xt:
32
- Oxi cn cp e cha chia nn tham gia lin kt vi nhn thm gy hiu ng
+C. Kt qu lin kt -O-H phn cc mnh, phenol c tnh axit mnh hn
monoancol.
- OH gy hiu ng +C y e l nhm th loi 1 tng hot do vy n s nh
hng nhm th mi vo v tr o v p.
3.3.2. iu ch
Phng php ch yu nht l thu phn clobenzen
3000 C
C6H5 Cl + 2NaOH C6H5ONa + NaCl +
H2O 140-210 atm
+ HCl
C6H5 OH + NaCl
Hoc: 4000 C
C6H5Cl + H2O C6H5OH + HCl

xc tc
3.3.3. Ho tnh
3.3.3.1. Tnh axit
Trong dung dch nc
C6H5 OH + H2O C6H5O- + H3O + Ka =
-10
10
Phenol lm hng qu tm, tc dng c vi kim loi, baz
C6H5OH + K C6H5OK + 1/2H2
C6H5OH + NaOH C6H5ONa + H2O
Tnh axit ca phenol tuy mnh hn monoancol nhng vn l mt axit yu,
yu hn c H2 CO3.
C6H5ONa + H2CO3 C6H5OH + NaHCO3
3.3.3.2. Phn ng th
Nhm -OH l nhm th loi 1 nh hng nhm th mi vo v tr o v p
Tc nhn th: X2, (dung dch Br2), HNO3 long, H2 SO4long ...
OH
OH Br Br
+ 3Br2 dd
Br trng
OH OH
O2N NO2
H2 SO4
+ 3HNO3 + 3H2 O
33
NO2
3.3.3.3. Phn ng nh tnh
Phenol c nhn bit bng thuc th c trng l dung dch FeCl3
6C6H5OH + FeCl3 H3[Fe (C6 H5O)6] + 3HCl
phc tm hoa c
3.3.3.4. Phn ng cacboxyl ho (phn ng Kolbe)
OH
ONa OH
COOH
CO2 COONa H+
0
120 C, 5atm
axit salixylic
salixylatnatri
Salixylat dng xoa bp thp khp cp tnh

Axitsalixylic dng iu ch nhng phm vt quan trng.
OH OCOCH3
COOH + Cl CO CH3 COOH

+ HCl
axetylsalixylic
(Aspirin)
OH OH
COOH + C6 H5 OH COOC6 H5
+ H2 O
salixylatphenyl
(Salol)
Aspirin: tr bnh nhc u

Salol: thuc cha ng rut, st trng ng niu, cha bnh phn trng
gia sc.
34
35
CHNG IV: HP CHT CACBONYL GLUXIT
4.1. Hp cht cacbonyl

Hp cht cacbonyl l loi hp cht trong phn t c cha nhm chc cacbonyl (- CO -)
C 2 loi:
Hp cht andehyt: R- C - H (R - CHO)
O
Hp cht xeton: R - C - R' (R - CO - R')
O
Ch yu xt hp cht cacbonyl thng, no
4.1.1. Danh php
i vi andehyt
- Tn thng: mang tnh cht lch s (gi theo axit tng ng)
- Tn quc t: tn hydrocacbon + al
H - CHO : metanal (andehyt focmic)
CH3 - CHO : etanal (andehyt axetic)
Nu l nhm ph th c tn nhm l focmyl
OHC - CH2 - CH2 - COOH : axit 3- focmylpropanoic
i vi xeton
- Tn thng: tn gc hydrocacbon + xeton
- Tn quc t: v tr + tn hydrocacbon + on
CH3 - CO - CH3 : propanon (dimetylxeton hay axeton)
CH3 - CO - CH3 - CH2 - CH3 : 2-pentanon (metylpropylxeton)
Nu l nhm ph th c tn l oxo hay l xeto
CH3 - CO - CH2 - COOH : axit 3-oxobutanoic
4.1.2.1. Oxi ho ancol
4.1.2.2. Hydrat ho ankyn
Ch ring H - CHO th kh cn cc andehyt khc th lng (C2 - C7 ) v th rn (C8 ...)
Andehyt focmic l cht tiu biu nht ca hp cht andehyt, tan tt trong nc, c mi
xc, dung dch HCHO 30 - 40% gi l focmon c dng trong ngnh y v nng lm ngm
xc sinh vt v x l ht ging.
Axeton l cht tiu biu ca hp cht xeton c s dng lm dung mi.
34
4.1.3. Ho tnh
C O
Nguyn t C lun lun mang 1 phn in tch dng, in tch dng cng ln th kh
nng phn ng cng d.
4.1.3.1. Phn ng cng
Phn ng tng qut:
C=O + X+ - Y- C - OX
Y
C ch: cng nucleophin (AN)
Tc nhn tn cng u tin l phn t mang in tch m (tc nhn nucleophin). Phn
ng xy ra qua 2 giai on:
chm
C =O + Y- CY - O-
nhanh
- +
CY - O + X CY - OX
Kh nng phn ng: andehyt > xeton

R C H R C R'
O O
(+) > ' (+)

Cc phn ng cng thng gp:
- Cng HCN: c andehyt v xeton u phn ng
C=O + HCN C(OH) - CN

Sn phm to thnh d b thu phn to axit cacboxylic
H+ OH
C(OH )- CN + 2H2 O C + NH3
COOH
C th dng xc tc l OH- khi sn phm l mui ca axit hu c.
- Cng dn xut NH3 : c andehyt v xeton u phn ng
Dn xut NH3 : H2 N - A
H2 N - OH: hydroxylamin
H2 N - NH - C6 H5 : phenylhydrazin
35
H+
- CO - + H2N - OH C = N - OH + H2 O
H+ (oxim)
- CO - + H2N - NH - C6 H5 C = N - NH - C6 H5 + H2 O
(phenylhydrazon)
- Cng hp bisunfit: tt c andehyt v ch ring metylxeton (CH3 - CO -) tham gia
phn ng.
O OH
CH3 - CHO + S ONa CH3 - CH
OH SO 3Na
(sn phm cng bisunfit)
- Cng hp cht c magie: sn phm l ancol cc bc
4.1.3.2. Phn ng oxi ho
Cng nh phn ng cng andehyt tham gia phn ng d dng hn xeton.
* i vi cht oxi ho yu: ch c andehyt phn ng
- Thuc th Tollens:
Thnh phn: AgNO3 / NH3 long d ( thc cht l Ag(NH3 )2 OH )
t0
R - CHO + 2Ag(NH3 )2 OH R - COONH4 + 2Ag bc sng + 3NH3 + H2 O
Phn ng trng gng
Phn ng trng gng c ng dng nhiu trong thc tin
- Thuc th Feling:
Thnh phn: FeLing A v FeLing B (t l 1:1)
COOK COOK
H H
CH O O- CH + H2 O
Cu
CH O O- CH
| |
COONa COONa
Tactrat kali natri ng
t0 COOK
R - CHO + thuc th Feling R - COOH + Cu2 O gch + CH - OH
CH - OH
COONa
36
* i vi cht oxi ho mnh
Vi hn hp (KMnO4 + H2 SO4 ) hoc (K2 Cr2 O7 + H2 SO4 ) xeton mi b oxi ho,
phn ng xy ra lm t mch C, sn phm l axit cacboxylic.
[O]
R - CO - CH2 - R' R - COOH + R' - COOH
(Ct mch v pha C bc cao)
4.1.3.3. Phn ng vi thuc th Schiff
Thuc th Schiff:
H2 N NHSO3 H
C
H2 N CH3 SO3 H
R- CH - SO2 NH
RCHO + t2 Schiff (+)
C NH
(khng mu) OH
R- CH - SO2 NH
OH CH3
(dung dich mu hng)

Tt c andehyt v ch ring axeton tham gia phn ng ny
4.1.3.4. Phn ng halofoc
Xy ra vi cc hp cht cha nhm CH3 - CO - (metylxeton)
t0
CH3 - CO - CH3 + 3I2 + 4NaOH CHI3vng nht + CH3 - COONa + 3NaI + 3H2 O
C ch: I2 OH-
O-
CH3 - CO - CH3 CH3 - CO - CI3 CH3 - C - CI3
OH
CHI3 + CH3 COO- -

CI3 + CH3 - CO - OH
4.1.3.5. Phn ng th H
Cc Hlinh ng d b th bi cc nguyn t halogen.
t0 , p, H+
CH3 - CHO + Cl2 CH2 Cl - CHO + HCl
D Cl2 s th tip v cho cc sn phm th CHCl2 - CHO v CCl3 -CHO.
37
Cc cht tiu biu
1. HCHO: andehyt fomic
L cht kh khng mu, mi xc, tan tt trong nc.
Dung dch HCHO 30 - 40% gi l focmon
Focmon c s dng
- Ngm tiu bn
- p xc ng vt
- Lm cht st khun
- X l ht ging
2. CH3 -CHO: andehyt axetic
L cht lng d bay hi, mi xc, tan tt trong nc CH3 -CHO c nhiu ng dng.
- iu ch axit axetic: l ho cht c bn trong k ngh ho hc
- iu ch thuc tr su D.D.T
t0, p
CH3 - CHO + 3Cl2 CCl3 - CHO + 3HCl
H+
oleum Cl
Cl3 C CHO + 2H Cl Cl3 C- CH + H2 O
Cl
D. D . T
(diclodiphenyl tricloetan)
Lu :
+ i vi hp cht cacbonyl cha no ngoi cc tnh cht trn cn c tnh cht ca lin kt bi.
+ i vi hp cht cacbonyl thm ngoi tnh cht trn cn c tnh cht ca nhn thm.
Nu -CHO gn trc tip vo nhn thm: - CHO gy hiu ng -C ht e nn l nhm gim
hot hn ch lm gim kh nng phn ng v nh hng nhm th mi vo v tr m.
Nu -CHO khng gn trc tip: tu trng hp c th ca tng cht.
4.2. Gluxit.
Gluxit l hp cht tp chc trong phn t cha ng thi 2 nhm chc: chc cacbonyl -
CO - v chc ru - OH.
Gluxit cn c gi l cacbonhydrat
Cng thc tng qut: Cn (H2 O)m
Gluxit c chia lm 3 loi chnh:
- Monosaccarit Oligosaccarit Polisaccarit
38
4.2.1. Monosaccarit
4.2.1.1. Danh php
Danh php monosaccarit tu thuc 2 yu t:
- S C trong phn t:
3C : triose 5C: pentose
4C: tetrose 6C: hexose
- Nhm chc trong phn t:
Nhm aldehyd: gi l aldose
Nhm ceton: gi l cetose
Chng hn:
CH2 OH - (CHOH)3 - CHO : aldopentose
CH2 OH - (CHOH)4 - CHO : aldohexose
CH2 OH - (CHOH)3 - CO - CH2OH: cetohexose
4.2.1.2. Cu to
1. Cu to thng
a s cc monosaccarit u c ng phn quang hc. biu din cc ng phn ta
dng cng thc Fischer.
Xt 2 dang in hnh: aldohexose v cetohexose.
* Xt phn t aldohexose
Cu to thu gn: CH2 OH - (C* HOH)4 - CHO
Phn t c 4C* nn c N = 24 = 16 ng phn quang hc (8 cp i quang)
Trong 8 cp i quang th c 2 cp tiu biu D, L glucose v D, L galactose.
CHO CHO CHO CHO
H OH HO H H OH HO H
HO H H OH HO H H OH
H OH HO H HO H H OH
H OH HO H H OH HO H
CH2 OH CH2 OH CH2 OH CH2 OH
D-glucose L-glucose D-galactose L-galactose
* Xt phn t cetohexose
Cu to thu gn: CH2 OH - (C* HOH)3 - CO - CH2 OH
Phn t c 3C* nn c N = 23 = 8 ng phn quang hc (4 cp i quang)
39
Trong 4 cp cp D, L fructose l tiu biu nht.
CH2 OH CH2 OH
C=O C=O
HO H H OH
H OH HO H
H OH HO H
CH2 OH CH2 OH
D-fructose L-fructose
Hu ht cc monosaccarit dng D c nhiu ng dng hn dng L

** Hn ch ca cu to thng
Cu to thng khng gii thch c mt s trng hp sau:
- Mt s aldose khng phn ng c vi NaHSO3 , thuc th Schiff ...
- Phn t c nhm - OH c bit so vi cc nhm - OH khc ( - OH gn vi C nhm
chc).
- S lng ng phn quang hc tm c bng thc nghim ln hn nhiu so vi
l thuyt.
gii thch cc hin tng ny hai nh bc hc Kolli v Tollens cho rng ngoi cu
to thng cc monosaccarit cn c cu to vng.
2. Cu to vng
a. Xt cu to vng ca D - glucose:
Ch yu xy ra qu trnh to vng 6 cnh C1 v C5 .
CH2OH
H O H
CHO H
OH H OH
HO
H OH
H OH
HO H D - glucopyranose
H OH
CH2OH
H OH
H O OH
CH2 OH H
OH H
HO H
D-glucose
H OH
D-glucopyranose
40
Nhn xt:
- dng vng cc aldose khng cn nhm - CHO t do nn khng do vy n khng tc
dng c vi mt s cht nh NaHSO3 , thuc th Schiff ...
- Khi to vng xut hin thm 1 nhm - OH C nhm chc (C1 ), - OH ny gi l - OH
glucosid hay - OH bn axetal, n c tnh cht khc bit so vi cc - OH khc (c kh nng m
vng, to c hp cht glucosid ...)
- Thm 1C* trong phn t (C1 * ) v vy s ng phn quang hc tng ln.
Nh vy cu to vng gii thch c mt s vn m cu to thng khng gii
thch c.
b. Xt cu to vng ca D - fructose:
Ch yu xy ra qu trnh to vng 5 cnh C2 v C5 .
HOCH2 O CH2OH
CHO H HO OH
H
C O
OH H
HO H
H OH D-fructofuranose
H OH
HOCH2 O OH
CH2 OH
H H HO CH OH
D- fructose 2
OH H
D-fructofuranose
4.2.1.3. Ho tnh
1. Phn ng ca nhm cacbonyl
a. Phn ng cng
Cng H2 : sn phm to thnh l cc polipol
Glucose ch to 1 poliol
Fructose to c 2 poliol
Cng HCN: sn phm to thnh l cc polioxinitrin
OH
CH2 OH - (CHOH)4 - CHO + HCN CH2 OH - (CHOH)4 - CH
(c) (khng c) CN
b. Phn ng oxi ho
** i vi cht oxi ho yu: thuc th Tollens, FeLing.
41
Phn ng xy ra d dng vi cc aldose, vi cetose th chm hn.
CH2 OH-(CHOH)4 -CHO + Ag(NH3 )2 OH t0 CH2 OH-(CHOH)4 -COONH4 + Ag

+ NH3 + H2 O
S d cc xetose cng tham gia phn ng ny l do c qu trnh ng phn ho xy
ra trong mi trng kim.
OH- OH-
cetose enol aldose
C th:
CH2 OH H OH
C CHO
C=O C - OH H OH
HO H OH H OH H
OH- OH-
H OH H OH H OH
H OH H OH H OH
CH2 OH CH2 OH CH2 OH
D-fructose enol D-glucose
Do vy thuc th Tollens v Feling khng phi l thuc th c trng phn bit 2
dng andose v xetose trong monosaccarit.
Thuc th c trng phn bit 2 dng ny l thuc th Selivanop.
Thuc th Selivanop: HCl / Resorcin
Khi cho 2 dng andose v xetose tc dng vi thuc th Selivanop ch c dng xetose
tham gia phn ng. Sn phm thu c l hp cht mu anh o.
Phn ng xy ra nh sau:
OH
OH
HO C H 2 O C H 2O H
2 OH OH
H H HO O H HCl
HOCH2 CH
CHO
OH H HOCH2 OH
OH
hp cht anh o
** i vi cht oxi ho mnh: HNO3

i vi aldose c nhm - OH bc 1 cng b oxi ho
HNO3d
CH2 OH - (CHOH)4 - CHO HOOC - CHOH)4 - COOH
42
i vi cetose khi b oxi ho chng thng b oxi ho dng h bin enol v phn t
b ct mch.
Chng hn D-fructose khi b oxi ho cho sn phm l axit tactric va axit oxalic
* * * Nhn chung i vi phn ng ca nhm cacbonyl th kh nng phn ng ca monosaccarit
mnh hn so vi hp cht cacbonyl, s d nh vy l do trong monosaccarit xut hin hiu ng
-I tng h gia cc nhm OH.
2. Phn ng ca nhm OH: c trng nht l phn ng este ho.
Este quan trng nht l este photphat
CH2OH
H O H H3 PO4 D glucose 6 P
H
OH H D glucose 1 P
HO OH
H OH D glucose 1, 6 di P
Fructose cng cho sn phm tng t
Cc sn phm ny tham gia vo cc chu trnh trong c th sng (qu trnh ng phn,
chu trnh pentophotphat ...) to ra nng lng cho c th.
4.2.2. Oligosaccarit
Oligosaccarit l hp cht bao gm t 2 -10 gc, monosaccarit kt hp vi nhau trong
ch yu nht l disaccarit.
Disaccarit l nh ng gm 2 monosaccarit kt hp vi nhau bng cch loi mt phn
t nc. Cng thc tng qut: C12 H22 O11
Da vo cu to v tnh cht ngi ta chia thnh 2 loi.
4.2.2.1. Disaccarit khng c tnh kh: in hnh l saccarose
- Saccarose c nhiu ma v c ci ng phn t, c hnh thnh t D glucosev
D fructose lin kt nhau bng lin kt , -1,2 glucosid.
CH2OH
CH2OH
HOCH2 O OH
O
O H
H
+ HO H
H OH CH2OH HO
HO
OH
OH OH
HOCH2 O + H2 O
HO
CH2OH
OH
saccarose
43
- Saccacrose khng cn nhm - OH bn axtal nn khng c tnh kh tc khng tc
dng c vi cc cht oxi ho: thuc th Tollens, Feling ...
- Di tc dng ca axit hay enzym saccarose b thu phn ti to cc cht ban u D
glucose v D fructose.
enzym
C12 H22O11 + H2O C6 H12 O6 + C6 H12 O6
H+
saccarose D glucose D fructose
[D: + 66,50 + 52,50 - 92,40
-39,90
V v saccrose c gi l ng nghch o
4.2.2.2. Disaccarit c tnh kh: in hnh l maltose

- Maltose c nhiu la i mch phn t c hnh thnh t 2 gc D glucose lin
kt nhau bng lin kt -1,4 glucosid.
CH2OH CH2OH CH2OH CH2OH

O O O O
H H H H
+ + H2 O
H H H O H OH
HO OH HO OH HO
OH OH OH OH
mantose
- Phn t cn 1 nhm -OH bn axetal nn c tnh kh di tc dng ca cht oxi ho
vng ete b t ra l nhm -CHO t do.
O O
O COOH
CHO
OH
Di tc dng ca axit hay enzym maltose b thu phn to thnh 2 phn t glucose.
C12 H22O11 + H2O H+ 2C6 H12 O6
enzym
maltose D glucose
4.2.3. Polisaccarit
Cng thc tng qut: (C6 H10 O5 )n
Hp cht quan trng: tinh bt, cellulose
4.2.3.1. Tinh bt
Tinh bt l ngun thc n chnh ca con ngi v ng vt, tinh bt c nhiu go, m,
khoai, sn ...
44
1. Cu to:tinh bt c cu to bi 2 phn
- Amylose: chim khong 10-20% tinh bt c cu to bi cc gc D gluco lin kt
nhau bng lin kt -1,4 glucosid to mch thng.
O O O
O O O
lin kt -1,4
- Amylopectin: chim khong 80 -90% tinh bt c cu to bi nhng phn t D
glucose lin kt nhau bng lin kt -1,4 v -1,6 glucosid.
O O
O O
lk -1, 4 glucosid O lk glucosid

CH2
O O
O O O
2. Tnh cht
Tinh bt d b thu phn bi axit hoc enzym
H2 O H2 O H2 O
(C6 H10O5 )n (C6 H10O5 )x C12 H22O11 C6 H12 O6
+ + +
H , enzym H , enzym H enzym
tinh bt dextrin mantose D glucose
4.2.3.2. Xenlulo
Xenlulo l thnh phn chnh ca mng t bo, thc vt cellulose chim khong 40-
50%, c bit si bng cellulose chim n 90%.
Xenlulo khng tan trong nc, khng c tnh kh, phn t lmg rt ln (250.000
1.000.000) bao gm trn 1500 gc glucose
1. Cu to:
Xenlulo c to thnh t cc phn t D-glucose lin kt nhau bng lin kt -1,4
glucosid.
O O O
O O O
O
lk -1,4 glucosid
45
2. Tnh cht
a. Phn ng thu phn
H2 O H2 O H2 O
(C6 H10O5 )n (C6 H10O5 )x C12 H22O11 C6 H12 O6
H +
H+ H+
xenlulo amyloit xenlobio D-gluco
Xenlulo t b thu phn bi enzym, enzym xenlulaza rt him ch c mt vi ng vt
c bit: (ng vt nhai li, c sn, mi ... ). Cc ng vt ny t phn xenlulo do v xenlulo
l thc n chnh ca n.
b. Phn ng ca nhm - OH
Do c cu to thng nn cellulose l cc nhm -OH ra ngoi, mi mc xch l 3
nhm -OH. V vy cng thc xenlulo c th c vit: [C6 H7 O2 (OH)3 ]n
Cc phn ng quan trng:
- Tc dng vi NaOH c
[C6 H7 O2 (OH)3 ]n + 3nNaOH [C6 H7 O2 (ONa)3 ]n + 3nH2 O
Phn ng ny c dng nh bng vi si
- Tc dng vi axit
[C6 H7 O2 (OH)3 ]n + 3nCH3 COOH [C6 H7 O2 (OCOCH3 )3 ]n + 3nH2 O
Axetat xenlulo c dng lm cht do, phim nh, sn ...
46
CHNG V. AXIT CACBOXYLIC - DN XUT AXIT
5.1. Axit cacboxylic

Axit cacboxylic l hp cht trong phn t c cha nhm cacboxyl - COOH.
Cng thc tng qut: Cn H2n+1 - COOH hay R - COOH
Tu thuc gc R v s nhm -COOH ta c cc loi
Gc R S nhm - COOH
Axit no, cha no, thm Axit mono, di, policacboxylic
Chng ta xt ch yu dng axit monocacboxylic no.
5.1.2. Danh php
- Tn thng: mang tnh cht ngu nhin lin quan n lch s hay ngi tm ra n.
- Tn quc t: axit + tn ankan + oic
HCOOH axit metanoic (axit focmic)
CH3 COOH axit etanoic (axit axetic)
C15 H31COOH axit hexadecanoic (axit panmitic)
C17 H35COOH axit octadecanoic (axit stearic)
5.1.3.1. Phng php oxi ho
Oxi ho cc hp cht c bc oxi ho C thp: anken, ankyn, ancol, hp cht cacbonyl....
5.1.3.2. Phng php thu phn
Thu phn cc dn xut ca axit: este, hp cht nitrin, anhydrit axit, clorua axit ...
H+
R - COOR' + H2 O R - COOH + R'OH
este
H+
R- C N + 2H2 O R - COOH + H2 O
nitrin
Cc axit t C1 - C3 l nhng cht lng khng mu, d bay hn, c mi dm, c ts0 kh
cao v tan v hn trong nc.
Nguyn nhn c t s0 cao v tan tt trong nc l do to c lin kt hydro.
O H O
R C C R
O H O
47
O H O H O H O H
C R H C R H
O O
Cc axit t C4 - C9 l nhng cht lng, snh t tan trong nc c mi kh chu.
Cc axit t C10 tr i l nhng cht rn, khng mi, khng tan trong nc.
5.1.4. Ho tnh
R C O H
O
- Nhm - CO - va gy hiu ng -I va gy hiu ng - C lm s phn cc lin kt O -
H tng, axit cacboxylic c tnh axit r rt.
- R cng ln, cng phc tp th tnh axit cng yu.
5.1.4.1. Phn ng t lin kt O - H
1. Tnh axit
Trong dung dch nc:
R - COOH + H2 O R - COO- + H3 O+
Th hin:
R - COOH + Na R - COONa + 1/2H2
R - COOH + KOH R - COOK + H2 O
2. Phn ng to anhydrit
Di tc dng ca nhng cht ht nc nh H2 SO4 , P2O5 hai phn t axit mt 1 phn
t nc to anhydrit.
O
R C
O O P2O5
O + H2O
R C + C R 0
t R C
OH HO
Hot tnh anhydrit mnh hn axit tng O
ng
5.1.4.2. Phn ng lm t lin kt C - OH
1. Phn ng este ho
Phn ng xy ra gia axit v ancol cho este v nc
2. Phn ng to amit
R - COOH + NH3 to R - CO - NH2 + H2 O
3. Phn ng to halogenua axit
to
R - COOH + PX5 R - CO - X + POX3 + HX
to
R - COOH + SOX2 R - CO - X + SO2 + HX
48
5.1.4.3. Phn ng gc hydrocacbon
1. Phn ng oxi ho
Nhm -COOH khng b oxi ho (tr HCOOH b oxi ho nhm -CHO) nhng gc
hydrocacbon trong axit c th b oxi ho tu iu kin.
Trong c th sinh vt gc hydrocacbon b oxi ho bi tc dng ca cc enzym, qu
trnh oxi ho ch yu xy ra v tr C .
enzym enzym RCOOH

R - CH2 - CH2 - COOH R - CO - CH2 - COOH +
[o] [o] CH3 COOH
Axit bo RCOOH mi to thnh li tip tc qu trnh chuyn ho nh ban u. Sn phm
cui cng ca s oxi ho l CH3 COOH tn ti di dng CH3 COSCoA (axetyl coenzym A),
CH3 COSCoA l sn phm quan trng trong qu trnh chuyn ho cht, tham gia vo chu trnh
Crebs to nng lng cung cp cho hot ng sng ca c th.
2. Phn ng th H
Tng t hp cht cacbonyl cc H linh ng d tham gia phn ng th bi cc
halogen.
t0 , p, H+
CH3 - COOH + Cl2 CH2 Cl - COOH + HCl

Nu tha Cl2 c th to thm cc sn phm CHCl2 - COOH v CCl3 - COOH
Cc cht tiu biu
1. HCOOH: axit focmic
HCOOH c nhiu ong v kin, l cht lng khng mu, mi xc, c tnh st khun,
c th gy bng da.
HCOOH b oxi ho to sn phm CO2 v H2 O
[O]
H - COOH HO - CO - OH CO2 + H2O
2. CH3 COOH: axit axetic
Axit ny c t thi thng c (dung dch 3 - 5%: gim n)
Mui ca axit axetic c nhiu ng dng:
(CH3 COO)2 Pb. Pb(OH)2 : ch axetat baz dng cha bng hay bong gn.
(CH3 COO)3 Al, (CH3 COO)3 Fe: dng lm cht cm mu.
3. C17 H35COOH: axit stearic
L loi axit bo cao no thng tn ti trong cht bo rn (m) trn vi parafin dng lm
nn, mui natri v kali ca chng l x phng.
5.2. Dn xut ca axit
Dn xut ca axit l hp cht thu c khi thay th H trong phn gc hoc -OH trong
nhm chc bng nhm th khc.
49
Chng hn:
R - C - OR' R- C - X R - C - NH2 R - CH - COOH R - CH - COOH
O O O OH NH2
este halogenua axit amit oxiaxit aminoaxit
Trong phn ny chng ta ch kho st dn xut quan trng nht ca axit l este
5.2.1. Khi nim Phn loi
Este l dn xut ca axit khi thay th nhm - OH bng nhm - OR'.
C 2 loi: este n gin (este hoa qu hay este) v este phc tp (lipit hay cht bo).
5.2.2. Este n gin
Cng thc tng qut: R - CO - OR'
* Tn gi: este + tn gc hydrocacbon + tn gc axit
CH3 - COOC2 H5 este etylaxetat
CH3 - COO(CH2 )2 CH(CH3 )2 este isoamylaxetat
H - COOC6 H5 este fomiatphenyl
* iu ch:
+ Thc hin phn ng este ho: xc tc H+
H+
R - COOH + R'OH R - COOR' + H2 O

+ i t halogenua axit: xc tc H+
H+
R - CO - X + R'OH R - COOR + HX
* Tnh cht
+ a s chng l nhng cht lng khng mu, d bay hi, khng tan trong nc,
nh hn nc v c mi thm d chu (mi thm hoa qu: l, to, chui ...)
+ Phn ng c trng ca este l phn ng thu phn. Qu trnh thu phn xy ra
c th thc hin trong mi trng axit hoc baz.
H+, (OH-)
R - COOR' + H2 O R - COOH + R'OH
Este n gin (este) c dng nhiu trong k ngh v hng liu.
5.2.3. Este phc tp
Mt loi hp cht cng c gi l este l lipit hay cht bo thuc loi este phc tp
Lipit l hp cht rt quan trng i vi con ngi, n l ngun nng lng d tr cho
c th, l thnh phn c bn cu thnh nn c th sng.
Lipit ng vt gi l m, lipit thc vt gi l du.
50
C 2 dng:
* Lipit n gin: l este ca glyxerin v axit bo, lipit n gin cn gi l glyerit.
Cng thc tng qut:
CH2 - O - CO - R1
CH - O - CO - R2
CH2 - O - CO - R3
R1 , R2 , R3 c th ging hay khc nhau c th no hay cha no.
CH2 - O - CO - C17 H35 CH2 - O - CO - C15 H31
CH - O - CO - C17 H35 CH - O - CO - C17 H33
CH2 - O - CO - C17 H35 CH2 - O - CO - C17 H35
tristearin panmito-oleo-stearin
(glyxerit n gin) (glyxerit phc tp)
Tnh cht:
1. Phn ng thu phn
Lipit d b thu phn trong mi trng kim
CH2 OCOR1 CH2 OH R1 COONa
t0
CHOCOR2 + 3NaOH CHOH + R2 COONa
CH2 OCOR3 CH2 OH R3 COONa
x phng
Phn ng x phng ho
2. Phn ng hydro ho
Phn ng chuyn du thnh m
Cc lipit th lng (du) c th b hydro ho to thnh dng rn (m). Qu trnh ny
thc cht l cng H2 vo lin kt i trong gc hydrocacbon.
t0
- (CH2 )n - CH = CH - (CH2 )m- + H2 - (CH2 )n - CH2 - CH2 - (CH2 )m-
3. S ho i cht bo
Cht bo lu trong khng kh d b ho i c mi hi kh chu. Nguyn nhn do cht
bo b O2KK oxi ho thnh peroxit sau peroxit khng bn tip tc phn gii cho hp cht
cacbonyl, nhng sn phm ny c mi hi kh chu.
- (CH2 )n - CH = CH - (CH2 )m- - (CH2 )n - CH - CH - (CH2 )m-
[o] O O
- (CH2 )n - CHO + - (CH2 )m - CHO
51
* Lipit phc tp: thnh phn ngoi glyxerin, axit bo cn c mt cc cht khc, a phn
l gc photphat v hp cht cha nit.
C nhiu dng nhng in hnh l photphat.
Cng thc tng qut:
CH2 OCOR1
CHOCOR2 OH
CH2 - O - P
O X
Cht tiu biu:
CH2 OCOR1
CHOCOR2 OH
CH2 - O - P
O O - (CH2 )2 - N(CH3 )3
OH
Colinphotphatit (Lecitin)
Lecitinase c nhiu nc c rn, di tc dng ca enzym ny Lecitin s b thu phn
to thnh cht isolecitin (cht hoi huyt).
52
CHNG VI. HP CHT CHA NIT
6.1. Amin
6.1.1. Khi nim - phn loi
- Amin l dn xut ca NH3 khi thay th cc nguyn t H bng cc gc hydrocacbon.
- Tu thuc s nguyn t H b thay th ta c amin cc bc:

H
Amin bc 1: R- N
H
H
Amin bc 2: R- N
R
Amin bc 3: R
N - R''
R'
Ngoi ra ngi ta cn phn loi amin da vo cu to gc hydrocacbon: amin bo,
amin vng thm.
6.1.2. Amin bo
6.1.2.1. Danh php
- Tn thng: tn gc hydrocacbon + amin
CH3 - NH2 CH3 - NH - C2 H5 CH3 - N(CH3 ) - CH3
metyl metyletylamin trimetylamin
- Tn quc t:
i vi amin bc 1: nhm NH2 gi l amino.
V tr + amino + tn hydrocacbon
CH3 - CH2 - CH - CH3 CH3
NH2 CH3 - C - CH3
NH2
2-aminobutan 2-amino- 2- metyl propan
i vi amin bc 2 v bc 3: N tn nhnh + tn hydrocacbon + amin
CH3 - CH2 - N - CH2 - CH - CH3
CH3 CH3
Nmetyl Netyl-2- metylpropan amin
53
6.1.2.2. iu ch
1. Ankyl ho NH3
NH3 NH3
R- X R - NH3 X R - NH2 + NH4 X
RNH2 NH3
R- X R2 NH2 X R2 NH + NH4 X
R 2 NH NH3
R- X R3 NHX R3 N + NH4 X
2. Kh hp cht nitro, nitrin
Dng cc cht kh kh hp cht nitro, nitrin thnh amin tng ng
LiAIH4
R - NO2 R - NH2 + H2 O
[H]
LiAIH4
R- C N R - CH2 - NH2
[H]
3. Tch loi amit (phng php Hoffman)

Cho hp cht amit tc dng vi halogen trong mi trng kim
Phng php ny iu ch c amin c s nguyn t C nh hn amit l 1.
R - C - NH2 + Br2 + NaOH R - NH2 + NaBr + CO2 + H2O
O
6.1.2.3. Ho tnh
Cu to amin: R - N
N cn cp e t do c kh nng thu nhn proton H+ th hin tnh baz

1. Tnh baz
Trong dung dch nc:
R - NH2 + HOH R - NH3 + OH- R - NH3 + + OH-
Tnh baz c sp xp:
amin bc 2 > bc 1 > bc 3
Tnh baz mnh hay yu ph thuc vo kh nng thu nhn H+, kh nng ny li ph
thuc vo mt e, mt e cng ln kh nng thu nhn H+ cng d.
54
Nh vy, ng l amin bc 3 c tnh baz ln nht v mt e ca N ln nht nhng
thc t th ngc li l do nh hng hiu ng cn tr khng gian ca cc gc
hydrocacbon.
C th:
Hng s cn bng Kb ca mt s hp cht
Hp Cht Kb
NH3 1,76 . 10-5

CH3 NH2 4,4 . 10-4
(CH3 )2 NH 5,1 . 10-4
(CH3 )3 N 0,6 . 10-4
Tnh baz ca amin th hin:

- Lm qu tm ho xanh
- Phenolphtalein khng mu chuyn mu hng
- Tc dng vi axit
R - NH2 + HCl R - NH3 Cl
1:1
R - NH3 HSO4
R - NH2 + H2 SO4
2:1
(RNH3 )2 SO4
2. Phn ng axyl ho
i vi amin bc 1 v bc 2 mt nguyn t H ni vi N c th b thay th bi nhm axyl
ca axit cacboxylic hay anhydrit axit.
R - NH -H + R - C - O - C - R R - NH - CO - R + R - COOH
O O
R - NH - H + HO - C - R R - NH - CO - R + H2 O
O
Hot tnh: (RCO)2 O > R - COOH
3. Phn ng vi HNO2
y l phn ng c trng phn bit bc cc amin, thuc th: dung dch
(NaNO2 + HCl)
Vi amin bc 1 khi phn ng vi HNO2 (dung dch NaNO2 + HCl) cho kh N2

thot ra.
R - NH2 + HO - NO R - OH + N2 + H2 O
55
Vi amin bc 2 khi phn ng vi HNO2 cho hp cht nitrozoamin mu vng khng
tan trong nc.
R - NH - R' + HO - NO R - N - N = O + H2 O
R'
Amin bc 3 tc dng vi HNO2 ch to mui tan (khng c du hiu)

4. Tc dng vi hp cht c kim
Amin bc 1 v bc 2 tc dng c vi CH3 - MgI gii phng CH4
R - NH - R' + CH3 - MgI R - N - MgI + CH4
R'
6.1.3. Amin thm
* Amin thm l hp cht trong phn t c cha nhn thm gn trc tip vi nguyn t N.
NH2 NH - CH3 NH2
CH3
anilin metylanilin o. toludin

a s chng l nhng cht lng khng mu, c mi thm, t tan trong nc.
* Ho tnh
1. Tnh baz
Tnh baz ca amin thm yu hn nhiu so vi amin dy bo l do nh hng ca
nhn thm n nhm chc, nhn thm ht e lm gim mt e ca N. Kt qu lm gim kh
nng thu nhn H+ tc lm gim tnh baz.
Tinhs bazo
Kb NH3 = 1,76.10-5
Kb C6 H5NH2 = 4,8.10-10
Do tnh baz qu yu nn amin thm ch tc dng vi axit mnh.
NH3 Cl
NH2
+ HCl
Tnh baz ca amin thm c sp xp:

amin 1 vng > amin 2 vng > amin 3 vng
56
2. Tc dng vi HNO2
Amin vng bc 1 tc dng vi HNO2 to mui diazo
+
NH2 N N
HCl Cl- + 2H2 O

+ HNO2
0-50C
Mui diazo d b thu phn

OH
+
N N
1100 C
-
Cl + 2H2 O + N2 + HCl
Qu trnh ny gi l qu trnh diazo ho.

Amin vng bc 2 tc dng vi HNO2 to hp cht nitrozo mu vng khng tan.
NH - CH3 CH3 - N N = O
+ H2 O
+ HNO2
nitrozometylanilin
Amin vng bc 3 tc dng vi HNO2 cho sn phm o hay p. nitrozo c mu xanh ve.
N ( CH3 )2 N (CH3 )2
+ H2 O
+ HNO2
N=O
3. Phn ng th nhn
Nhm NH2 (nhm th loi 1) nh hng nhm th mi vo v tr o v p.

NH2 NH2
Br Br
+ H2 O
+ 3Br2dd
trng
Br
Phn ng xy ra theo c ch th i in t (SE)
57
4. Phn ng oxi ho
lu trong khng kh anilin s b oxi ho dn cho ra nhng phm vt khc nhau.
H
NH2 N NH2 NH O
OH
[O] [O]
OH O O
en anilin hidroquinon
6.2. Aminoaxit
- Amino axit l hp cht tp chc phn t cha ng thi 2 nhm chc: chc
cacboxyl- COOH v chc amin - NH2
Cng thc tng qut:
R - (COOH)n
(NH2 )m
Nu nhm -NH2 nm v tr C th c gi l axit amin.
Trong c th sinh vt c khong 22 axit amin c kh nng to protein.
Mt s axit amin ng vai tr quan trng i vi c th nu thiu s gy bnh l.
- Ngi ta c th phn loi amino axit da vo cc yu t sau:
+ Da vo cu to gc R
R' khng vng: hnh thnh amino axit khng vng
CH3 - CH - COOH Alanin
NH2
R vng: hnh thnh amino axit vng.
Loi vng thm
CH2 - CH- COOH OH

NH2
CH2 - CH- COOH

Phenylalanin NH2
Tyrosin
58
Loi d vng
Cc axit amin c tm quan trng nh: Tryptophan, Histidin..
+ Da vo s nhm n, m
n = 1, m = 1
H2 N - CH - COOH Serin
NH2
n = 2, m = 1
CH2 - (CH2 )3 - CH - COOH Lysin
NH2 NH2
n = 1, m = 2
HOOC - CH2 - CH2 - CH - COOH Axit glutamic
NH2
n = 2, m = 2
S - CH2 - CH - COOH Cystin
NH2
S - CH2 - CH - COOH
NH2
Ngoi ra ngi ta cn phn loi amino axit da vo mc quan trng ca n i vi
c th (cc axit amin khng thay th c).
Axit amin khng thay th c: rt cn thit cho c th nhng c th khng t tng
hp c.
Gm 9 axit amin:
Val, Leu, Ile, Met, Thr, Phe, Trp, Lys, His
Axit amin thay th c: c th t tng hp c.
6.2.2. Ho tnh
Do trong phn t cha ng thi 2 nhm chc: - COOH v - NH2 nn amino axit va
c tnh axit va c tnh baz (tnh lng tnh)
6.2.2.1. Tnh lng tnh
Trong dung dch nc aminoaxit in ly theo 2 kiu:
R - CH - COOH + H2 O R - CH - COO- + H3O+
NH2 NH2
R - CH - COOH + H2 O R - CH - COOH + OH-
+
NH2 NH3
59
Tuy nhin H3 O+ do axit in ly ra lp tc b nhm amino tip nhn nn trong dung
dch bao gi amino axit cng tn ti di dng ion lng cc.
R - CH - COOH R - CH - COO-
+
NH2 NH3
Trong dung dich H2 O c cn bng:
- Dung dich aminoaxit trong mi trng axit th axit lin hp chim u th.
- Dung dich aminoaxit trong mi trng baz th baz lin hp chim u th.
Tnh lng tnh th hin:
- Tnh axit:
Thc hin phn ng este ho, tc dng c vi baz ...
+ NaOH
R - CH - COONa + H2 O
R - CH - COOH NH2
+R'OH
NH2 R - CH - COOR' + H2 O
H+
NH2
- Tnh baz:
Phn ng c vi axit, HNO2 ...
+ HCl
R - CH - COOH
R - CH - COOH NH3 Cl
+HNO2
NH2 R - CH COOH + N2 + H2O
OH
6.2.2.2. Phn ng loi nc ca aminoaxit
Aminoaxit d tch nc t nhm NH2 v COOH to ra amit
Sn phm to thnh phu thuc vo v tr ca NH2 so vi COOH
6.2.2.3. Phn ng ngng t
Trong nhng iu kin nht nh cc aminoaxit c th tng tc nhau to chui
polipeptit v gii phng H2 O.
nH2 N - CH - COOH H2 N - CH - C - N - .- CH - C - N - CH - COOH

R R O H R O H R
+ (n-1) H2 O
60
6.2.2.4. Phn ng nh tnh
Thuc th: Nin hydrin
O O
C OH C
CH2 - CH- COOH + C CH-OH
NH2
C OH C + RCHO+ CO2
+ NH3
O O
ninhydrin dixetooxyhydrin en
Hp cht ny phn ng tip vi Ninhydrinc mt NH3 cho sn phm mu xanh tm
O O
C C
CN= C
C C
O O
(mu xanh tm)
Tm li:
R - CH - COOH + thuc th Ninhydrin hp cht mu xanh tm
NH2
6.2.2.5. im ng in ca axit amin
Trong dung dch aminoaxit lun tn ti di dng ion lng cc. Tu vo pH ca
mi trng m ta c th iu chnh aminoaxit trung ho in, mang in tch dng hay m.
Mi trng axit: ion H+ km hm s in ly ca nhm - COOH v aminoaxit s tch
in dng.
R - CH - COO- + H+ R - CH - COOH
+ +
NH3 NH3
Mi trng baz: ion OH- km hm s in ly ca nhm - NH2 v aminoaxit s tch
in m.
R - CH - COO- + OH- R - CH - COO-
+
NH3 NH2 . H2 O
Nh vy ta c th iu chnh pH ca mi trng axit amin trung ho v in.
Gi tr pH ti thi im axit amin trung ho v in gi l im ng in ca axit
amin.k hiu: pI.
61
Thng thng:
S nhm - COOH = NH2 pI = 6
S nhm - COOH > NH2 pI < 7
S nhm - COOH < NH2 pI > 7
Cng thc xc nh pI:
pKa + pKb
pI =
2
Ka: hng s axit ca nhm COOH
Kb: hng s baz cu nhm NH2
6.3. Protein
Protein l hp cht cao phn t c cu thnh t cc axit amin.
Protein l mt trong cc thnh phn c bn cu to nn t bo v m c th, l ngun
thc n chnh ca ngi v ng vt.
6.3.1. Phn loi
C 2 loi:
6.3.1.1. Protein n gin: thnh phn ch gm cc axit amin
Abumin: c lng trng trng
Globulin: c mch mu v huyt thanh
6.3.1.2. Protein phc tp:
Phn t c cu to bi 2 phn:
- Phn protein: gi l nhm ni hay apoprotein
- Phn khng phi protein: gi l nhm ngoi
Chng hn:
Nucleoprotein: nhm ngoi l axit nucleic, nucleoprotein l thnh phn to nn ribosom
Lipoprotein: nhm ngoi l lipit, liprotein ng vai tr vn chuyn lipit trong c th
6.3.2. Cc mc cu trc ca protein
6.3.2.1. Cu trc bc 1.
Cu trc ny c gi vng nh lin kt peptit.
Lin kt peptit c hnh thnh do s kt hp ca nhm -cacboxyl ca axit amin
ny vi nhm -amino ca nhm kia bng cch loi i 1 phn t H2 O.
H2 N - CH - C - N - ............. - CH - C - N - CH - COOH
u N R O H R O H R u C
(+) (-)
62
Chui polipeptit bao gi cng bt u t u N ( + ) v kt thc bng u C ( - )
** ngha:
- Cu trc bc 1 l yu t gp phn nghin cu bnh l phn t: thay i th t axit
amin d ch l 1 gc cng lm thay i hot tnh sinh hc dn n gy bnh.
- L bn phin dch m di truyn. Cu trc bc 1 xc nh mi quan h h hng gia
cc sinh vt.
6.3.2.2. Cu trc bc 2.
Cu trc ny c gi vng nh lin kt hydro.
Lin kt hydro c hnh thnh gia nhm - CO - ca lin kt peptit ny vi nhm
NH ca lin kt peptit kia, lin kt hydro c th xy ra trn mt mch hoc c 2 mch.
Nh c lin kt hydro m chui polipep c nhng hnh dng khc nhau: xon
(75%), xon xp (25%).
C
C
O
O
H
H C
N
N C
O
O
H
H
N
N
xon (75%)
6.3.2.3. Cu trc bc 3.
L cu trc khng gian ca ton mch polipeptit (s cun li ca cc chui polipeptit
c cu trc bc 2), cu trc ny c gi vng nh lin kt disunfua, lc ht VanderWaals.
Lin kt disunfua c hnh thnh gia 2 mch hay 1 mch polipeptit, lin kt ny c to
bi 2 nhm -SH ca 2 gc cysterin bin i thnh 1 gc cystin.
- NH - CH - CO - NH - CH - CO - - NH - CH - CO - NH - CH - CO -
CH2 - S - S - CH2 CH2 - S R
CH2 - S
- NH - CH - CO - NH - CH - CO -
trn 1 mch trn 2 mch R
Lc ht VanderWaals hnh thnh do s tng tc ca cc nhm th khng phn cc
c kch thc ln.
63
6.3.2.4. Cu trc bc 4.
Tp hp 2 hay nhiu cu trc bc 3 gi l "phn di n v" bng lin kt hydro,
lc ht VanderWaals ta c cu trc bc 4.
Cu trc bc 4 c hot tnh sinh hc cao.
V d: Hemoglobin (Hb) c cu to t 4 phn d i nv vi 1 nhm heme

(cha Fe2+).
Hb c chc nng vn chuyn O2 trong mu n cc c quan.
6.3.3. Ho tnh
6.3.3.1. Tnh lng tnh
Trong phn t protein vn cn nhm - NH2 v nhm - COOH t do nn c tnh
lng tnh nh axit amin
6.3.3.2. Phn ng thu phn
Protein b thu phn n cng cho cc axit amin
H2 O H2 O H2 O H2 O
Protein pepton polipeptit dipeptit axit amin
Tc nhn thu phn
Axit, baz: HCl, NaOH ...
Enzym : pepsin, tripsin
6.3.3.3. Phn ng nhn bit lu hunh trong protein
Cc protein c cha lu hunh c nhn bit bng thuc th (CH3 COO)2 Pb/NaOH
- u tin un nng protein vi NaOH
- NH - CH - CO - NH - + NaOH - NH - CH - CO - NH - + Na2 S + H2 O
SH OH
- Sau cho dung dch (CH3 COO)2 Pb vo nu c S s thy xut hin kt ta en ca
PbS.
(CH3 COO)2 Pb + Na2 S 2CH3 - COONa + PbS
64
I HC HU
TRUNG TM GING DY V THC HNH C BN
B MN HO
BI GING
HO HC HU C
Th.S. PHAN TH DIU HUYN
HU, 2007
MC LC
CHNG I. MT S NI DUNG C BN CA L THUYT

HA HU C
1.1. Phn ng hu co ......................................................................................................................... 1

1.1.1. Phn loi hp cht h u co ................................................................................................ 1
1.1.2. Phn loi phn ng hu co............................................................................................... 1
1.2. Bn cht lin kt trong Ha hu co............................................................................................ 2
1.2.1. Lin kt .......................................................................................................................... 2
1.2.2. Lin kt ........................................................................................................................... 3
1.3. Cu trc phn t cc hp cht hu co ....................................................................................... 3
1.3.1. ng phn cu to ............................................................................................................ 3
1.3.2. ng phn khng gian...................................................................................................... 3
1.4. Hiu ng ha hc.......................................................................................................................... 8
1.4.1. Hiu ng cm ng ............................................................................................................. 8
1.4.2. Hiu ng lin hp.............................................................................................................. 9
CHNG II. HYDROCACBON

2.1. Hydrocacbon no ........................................................................................................................... 11
2.1.1. Ankan................................................................................................................................. 11
2.1.2. Xycloankan ........................................................................................................................ 14
2.2. Hydrocacbon cha no.................................................................................................................. 15
2.2.1. Anken................................................................................................................................. 15
2.2.2. Ankadien............................................................................................................................ 17
2.2.3. Ankyn................................................................................................................................. 19
2.3. Hydrocacbon thm ...................................................................................................................... 21
2.3.1 Khi ni m - Phn loi ....................................................................................................... 21
2.3.2 Cu to benzen.................................................................................................................. 22
2.3.3. Danh php - V tr cc nhm th ..................................................................................... 22
2.3.4. iu ch - L tnh.............................................................................................................. 23
2.3.5. Ha tnh.............................................................................................................................. 23
CHNG III. DN XUT HALOGEN - ANCOL - PHENOL
3.1. Dn xut halogen.......................................................................................................................... 25
3.1.1. Danh php.......................................................................................................................... 25
3.1.1. iu ch - L tnh.............................................................................................................. 25
3.1.3. Ho tnh ............................................................................................................................. 26
3.2. Ancol.............................................................................................................................................. 27
3.2.1. Danh php.......................................................................................................................... 28
3.2.2. iu ch - L tnh.............................................................................................................. 28
3.2.3. Ho tnh.............................................................................................................................. 29
3..3. Phenol........................................................................................................................................... 31
3.3.1. Cu to phenol................................................................................................................... 32
3.3.2. iu ch .............................................................................................................................. 32
3.3.3. Ha tnh.............................................................................................................................. 32
CHNG IV. HP CHT CACBONYL - GLUXIT
4.1. Hp cht cacbonyl........................................................................................................................ 34

4.1.1 Danh php........................................................................................................................... 34
4.1.2. iu ch - L tnh.............................................................................................................. 34
4.1.3. Ho tnh.............................................................................................................................. 35
4.2. Gluxit............................................................................................................................................. 38
4.2.1. Monosaccarit ..................................................................................................................... 38
4.2.2. Disaccarit ........................................................................................................................... 43
4.2.3. Polisaccarit......................................................................................................................... 44
CHNG V. AXIT CACBOXYLIC - DN XUT CA AXIT

5.1. Axit cacboxylic.............................................................................................................................. 47
5.1.1. Khi ni m - Phn loi ....................................................................................................... 47
5.1.2. Danh php.......................................................................................................................... 47
5.1.3. iu ch - L tnh.............................................................................................................. 47
5.1.4. Ha tnh.............................................................................................................................. 48
5.2. Dn xut ca axit ......................................................................................................................... 49
5.2.1. Khi ni m Phn loi....................................................................................................... 50
5.2.2. Este ..................................................................................................................................... 50
5.2.3. Lipit .................................................................................................................................... 50
CHNG VI. HP CHT CHA NIT
6.1. Amin .............................................................................................................................................. 53
6.1.1. Khi ni m- Phn loi ....................................................................................................... 53
6.1.2. Amin bo........................................................................................................................... 53
6.1.3. Amin thm........................................................................................................................ 56
6.2. Amino axit.................................................................................................................................... 58
6.2.1. Khi ni m- Phn loi ....................................................................................................... 58
6.2.2. Ha tnh............................................................................................................................. 59
6.3. Protein.......................................................................................................................................... 62
6.3.1. Phn loi ........................................................................................................................... 62
6.3.2. Cc mc cu trc ca protein......................................................................................... 62
6.3.3. Ha tnh............................................................................................................................. 64
TI LIU THAM KHO
1. ng Nh Ti - Trn Quc Sn. Ha hoc hu c. Nxb i hc Quc gia, H

Ni (2003).
2. Hong Trng Ym. Ha hc hu c. Nxb Khoa hc v K thut, H Ni
(2003).
3. Trng Th K. Ha hc hu c. Trng i hc Y - Dc, T.P H Ch Minh
(1999).
4. Thi Don Tnh - Tp I,II. C s ha hc huc. Nxb Khoa hc v K thut ,
H Ni (2006).
5. Nguyn Hu nh - nh Rng. Ha hc hu c. Nxb Gio Dc H Ni,
(2006).
6. Trn M nh Bnh - Nguyn Quang t. Ho hc hu c. Trng i hc Dc
H Ni (2004)
7. inh vn Hng - Trn th T. Ha hc hu c. Nxb i hc v Gio dc
chuyn nghip, H Ni (1990).

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TRNG I HC NNG LM HU

D N HP TC VIT NAM H LAN

Ngi bin son: Phan Th Diu Huyn

CH3 Cl + NaOH CH3OH + NaCl (SN: th nucleophin)

CH3 - CH = CH2 + HBr CH3 - CH2 - CH2Br (AR)

Cc orbital p dng cha lai ho c hnh qu t i cn i.

C 2 loi ng phn khng gian:

dng cis dng trans

dng syn dng anti C6 H5

b. Trng hp vng no: cng tng t

cht hot quang

Phn t c 1C* th s c 2 cu hnh ging nhau nhng khng th chng kht

4. Danh php D,L

D (+) glucose L (-) glucose

- Hiu ng I gip ta gii thch tnh axit, baz v kh nng phn ng ca

Hydrocacbon l hp cht hu c m thnh phn phn t ch gm 2 nguyn t l C v H.

Hydrocacbon no Hydrocacbon cha no Hydrocacbon thm

ankan xycloankan ankan ankadien ankyn aren

1. Hydro ho anken: Cho anken tc dng vi H2 c Ni xc tc

2. i t mui axit hu c: Cho mui tc dng vi NaOH co mt CaO

3. Phng php ghp mch (Wurts - Fittig)

2. Phn ng hu: t0 cao khng c O2KK cc ankan b phn hu b gy mch C to thnh

2.2. Hydrocacbon cha no

Phn ng tun theo quy tc Zay Xep (tch H C bc cao)

(1) : phn ng tun theo qui tc Maccopnhicop

Mc ch phn ng ny dng xc nh v tr lin kt i trong hp cht u.

CH3 - C = CH - CH2 - CH2 - C = CH - CH2OH (tinh du hoa hng)

CH3 CH3 CH3 CH3

cis Retinal trans Retinal

Cu to benzen c th c biu din:

2.3.3. Danh php - V tr cc nhm th

metyl benzen isopropyl

1,2 - dimetyl benzen 1,3 -dimetylbenzen

Kh nng phn ng ph thuc vo cc nhm th c trn nhn.

Sn phm to thnh c 8 ng phn hnh hc, trong 8 ng phn ch c ng phn

3.1. Dn xut halogen

R-X Y- .... R ..... X- R - Y + Z - X-

Ngoi dn xut monohalogen no ra cc loi dn xut khc cng c nhiu ng

Ancol loi nc to anken: c H2SO4 xc tc t0 1700C

R CH2 CH2 OH R - CH = CH2 + H2O

R CHOH - R R - CO - R' + H2O

phenol o. cresol pyrocatechin resorcin hydroquinon

C6H5Cl + H2O C6H5OH + HCl

Salixylat dng xoa bp thp khp cp tnh

COOH + Cl CO CH3 COOH

Aspirin: tr bnh nhc u

4.1. Hp cht cacbonyl

(+) > ' (+)

C=O + HCN C(OH) - CN

Tactrat kali natri ng

(dung dich mu hng)

CHI3 + CH3 COO- -

Phn t c 3C* nn c N = 23 = 8 ng phn quang hc (4 cp i quang)

Hu ht cc monosaccarit dng D c nhiu ng dng hn dng L

** i vi cht oxi ho yu: thuc th Tollens, FeLing.

CH2 OH-(CHOH)4 -CHO + Ag(NH3 )2 OH t0 CH2 OH-(CHOH)4 -COONH4 + Ag

** i vi cht oxi ho mnh: HNO3

* * * Nhn chung i vi phn ng ca nhm cacbonyl th kh nng phn ng ca monosaccarit

mnh hn so vi hp cht cacbonyl, s d nh vy l do trong monosaccarit xut hin hiu ng

-I tng h gia cc nhm OH.

2. Phn ng ca nhm OH: c trng nht l phn ng este ho.

Este quan trng nht l este photphat

4.2.2.2. Disaccarit c tnh kh: in hnh l maltose