TT LUYN THI & BI DNG KIN THC NGY MI 18A/88 INH VN T - TP.

HI DNG

AMIN, AMINO AXIT, PEPTIT

A. AMIN
I. KHI NIM, PHN LOI, DANH PHP V NG PHN
1. Khi nim
- Khi thay th mt hay nhiu nguyn t hidro trong phn t NH3 bng 1 hay nhiu gc hirocacbon ta c phn t amin.
- Gc hirocacbon c th l gc no, cha no, thm
=> Khi gc no ngi ta gi l amin bo, khi gc l nhn thm gi l amin thm.

2. Phn loi
a) Theo c im cu to ca gc hirocacbon: amin thm, amin bo, amin d vng. V d:

b) Theo bc ca amin: Bc amin: l s nguyn t H trong phn t NH3 b thay th bi gc hirocacbon. Theo , cc
amin c phn loi thnh: amin bc 1, bc 2, bc 3. V d:

Note: Bc ca amin bng s nguyn t H c thay th trong phn t NH3 hay ni cch khc bng s gc hirocacbon
lin kt vi 1 nguyn t N.
3. Danh php
- Tn ca amin c gi theo danh php gc chc; tn thay th; v ngoi ra mt s c gi theo tn thng (tn ring).
- Nhm NH2 khi ng vai tr nhm th th gi l nhm amino, cn khi l nhm chc th gi l nhm amin.
a. Tn gc chc: tn gc hirocacbon + amin (vit lin nhau). (ank + yl + amin)
b. Tn thay th: tn hirocacbon + amin. (ankan + v tr + amin)
* Amin bc 1: Tn mch chnh s ch v tr nhm NH2 - amin
* Amin bc 2 v 3: (N hoc N,N (tri) + tn gc hidrocacbon + tn ca amin mch chnh (mch di nht)
c. Mt s tn thng thng ca amin
C6H5-NH2 : Anilin
Ch :
- Tn cc nhm ankyl c theo th t ch ci a, b, c
- Vi cc amin bc 2 v 3, chn mch di nht cha N lm mch chnh, N c ch s v tr nh nht. t mt nguyn t N
trc mi nhm th ca amin - Khi nhm NH2 ng vai tr nhm th th gi l nhm amino.
V d: CH3CH(NH2)COOH (axit 2-aminopropanoic)
Hp chat Ten goc - chc Ten thay the Ten thng
CH3NH 2 Metylamin Metanamin
C2H5NH2 Etylamin Etanamin
CH3CH2CH2 NH2 Propylamin Propan - 1 - amin
CH3CH(NH2)CH3 Isopropylamin Propan - 2 - amin
H 2N(CH2)6NH2 Hexametyleniamin Hexan - 1,6 - iamin
C6H5NH2 Phenylamin Benzenamin Anilin
C6H5NHCH3 Metylphenylamin N -Metylbenzenamin N -Metylanilin
C2H5NHCH3 Etylmetylamin N -Metyletanamin
4. ng phn:
S ng phn ca amin: 2 n-1 (1<n<5)
Bi ton: Vit ng phn amin C nH 2n+3N
1. ng phn amin bc 1.

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 TI LIU LUYN THI & BI DNG KIN THC NM 2011

Vit cc ng phn ca mch cacbon Cn. m tt c s cacbon bc 1, 2, 3 khng i xng (nu c 2 cacsbon i xng th ch tnh 1). chnh l s
ng phn bc I
2. ng phn amin bc 2.
Tng t, ta vit ng phn mch cacbon Cn. Sau m s ni n khng i xng. chnh l s ng phn bc 2.
3. ng phn amin bc 3.
Cch 1: Vit ng phn mch cacbon Cn+1 ri m s cacbon bc III khng i xng. chnh l s ng phn amin bc III.
Cch 2: Ta thy s ng phn amin bc III tun theo cng thc:
1 n 3 1 n 3
D 1 2
2

1 2
2

- ng phn v mch cacbon
- ng phn v tr nhm chc
- ng phn v bc ca amin
Ch : Nu nh trong phn t amin c cha lin kt i th s n cn bao gm c cc ng phn hnh hc na
V d:

C C C C C C C C N C C
C C
Amin bc 1: 4 ng phn Amin bc 2: 3 ng phn Amin bc 3: 1 ng phn
a) C4H11N Tng c 8 ng phn
+ + +
C
C C C C C C C C C C N C C C C C
C C C
Amin bc 1: 8 ng phn Amin bc 2: 6 ng phn Amin bc 3: 3 ng phn
b) C5H13N Tng c 17 ng phn

C C N C
C
Amin bc 1: 5 ng phn Amin bc 2: 2 ng phn Amin bc 3: 1 ng phn
c) Amin l dn xut ca benzene C8H11N. Tng c 8 ng phn
II. TNH CHT VT L
- CH3NH2, (CH3)2NH, (CH3)3N, C2H5NH2 l cht kh nhit thng, mi kh chu, c, d tan trong nc.
- Cc amin ng ng cao hn l cht lng hoc rn, tan trong nc gim theo chiu tng PTK.
- Nhit si ca cc amin cao hn cc ankan v thp hn ancol c cng PTK. Cc amin phn cc v xut hin lin kt
hiro, nhng lin kt hiro gia cc amin yu hn lin kt hiro gia cc ancol.
- Trong cc amin c bc khc nhau, amin bc ba si thp hn do khng c lin kt hiro, amin bc nht lun si cao hn
do c nhiu lin kt hidro hn.
III. CU TO PHN T V TNH CHT HA HC
1. Cu trc phn t ca amoniac v cc amin

2. Cu to phn t ca amoniac v cc amin

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Trn nguyn t nit u c cp electron t do nn NH 3 v cc amin u d dng nhn proton => u c tnh baz.
3. c im cu to ca phn t aniline
- Do gc phenyl (C6H5) ht cp electron t do ca nit v pha mnh, s chuyn dch electron theo
hiu ng lin hp p p (chiu nh mi tn cong) lm cho mt electron trn nguyn t nit gim i,
kh nng nhn proton gim i.
=> Tnh baz ca anilin rt yu (khng lm xanh c qu tm, khng lm hng c phenolphtalein).
- Nhm amino (NH2) lm tng kh nng th Br vo gc phenyl (do nh hng ca hiu ng +C). Phn
ng th xy ra cc v tr ortho v para do nhm NH2 y electron vo lm mt electron cc v tr
ny tng ln
4. So snh lc baz
a) Cc yu t nh hng n lc baz ca amin:
- Mt electron trn nguyn t N: mt cng cao, lc baz cng mnh v ngc li
- Hiu ng khng gian: gc R cng cng knh v cng nhiu gc R th lm cho tnh baz gim i, ph thuc vo gc
hirocacbon.
V d tnh baz ca (CH3)2NH > CH3NH2 > (CH3)3N ; (C2H5)2NH > (C2H5)3N > C2H5NH2
b) Phng php
Gc y electron lm tng tnh baz, gc ht electron lm gim tnh baz.
V d: p-NO2-C6H4NH2 < C6H5NH2 < NH3 < CH3NH2 < C2H5NH2 < C3H7NH2
1. Tnh cht ca chc amin
a. Tnh cht baz: tc dng ln giy qu tm m hoc phenolphtalein v tc dng vi axit
- Nguyn nhn gy tnh baz - So snh tnh baz ca cc cht
- Dung dch metylamin v nhiu ng ng ca n c kh nng lm xanh giy qu tm hoc lm hng phenolphtalein do
kt hp vi proton mnh hn amoniac
- Anilin v cc amin thm rt t tan trong nc. Dung dch ca chng khng lm i mu qu tm v phenolphtalein

b. Phn ng vi axit HNO2

- Amin bc mt dy bo tc dng vi axit HNO2 nhit thng cho ancol hoc phenol v gii phng N2.
- Anilin hoc amin thm bc mt tc dng vi HNO3 nhit thp cho mui iazoni.
- Amin no bc 1 + HNO2 ROH + N 2 + H2O. V d: C2H5NH2 + HONO C 2H5OH + N2 + H2O
- Amin thm bc 1 tc dng vi HNO2 nhit thp to thnh mui iazoni.

V d: C 6H 5NH2 + HONO + HCl C6H5N2+ Cl- + 2H2O

benzeniazoni clorua
c. Phn ng ankyl ha: ankyl bc mt hoc bc hai c th tc dng vi dn xut halogen (ankyl halogenua) CH3I, .
Phn ng ny dng iu ch amin bc cao t amin bc thp hn.
V d: C2H5NH2 + CH3I C 2H5NHCH3 + HI
d) Phn ng ca amin tan trong nc vi dung dch mui ca cc kim loi c hiroxit kt ta
3CH3NH2 + FeCl3 + 3H2O Fe(OH)3 + 3CH3NH3Cl
2. Tnh cht ca gc hirocacbon

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 TI LIU LUYN THI & BI DNG KIN THC NM 2011

C6H5-NH2 + 3Br2 => C6H2Br3NH2 + 3HBr

2,4,6-tribromanilin (kt ta trng)
IV. IU CH
a) Thay th nguyn t H ca phn t amoniac
Ankylamin c iu ch t amoniac v ankyl halogenua.
CH I CH I CH I
V d: NH 3 3
HI
CH 3 NH 2 3
HI
CH 3 2 NH 3
HI
CH 3 3 N
b) Kh hp cht nitro
Anilin v cc amin thm thng c iu ch bng cch kh nitrobenzen (hoc dn xut nitro tng ng) bi hiro mi
sinh nh tc dng ca kim loi (nh Fe, Zn) vi axit HCl.
0
t
V d: C6 H 5 NO2 3Fe 7 HCl C6 H 5 NH 3 Cl 3FeCl2 2 H 2O
Fe HCl
Hoc vit gn l: C6 H 5 NO2 6 H t0
C6 H 5 NH 2 2 H 2O
B. AMINO AXIT, PEPTIT

I. NH NGHA, CU TO V DANH PHP

1. nh ngha: Amino axit l loi hp cht hu c tp chc m phn t cha ng thi nhm amino (NH2) v
nhm cacboxyl (COOH) - Cng thc chung: (H2N)x R (COOH)y
Cc nhm chc c th gn vi nhng nguyn t cacbon no hay cacbon thm. Tuy nhin, cc amino axit c nhm
cacboxyl v nhm amino lin kt vi nguyn t cacbon no (nht l khi lin kt vi cng mt nguyn t cacbon no) c tm
quan trng c bit v nhiu cht trong s l nhng n v cu to ca phn t protein.
Hu ht cc amino axit thin nhin c trong thnh phn cu to ca protein l nhng -amino axit.
2. Cu to phn t:
- Trong phn t amino axit, nhm NH2 v nhm COOH tng tc vi nhau to ion lng cc.
=> V vy amino axit kt tinh tn ti dng ion lng cc
- Trong dung dch, dng ion lng cc chuyn mt phn nh thnh dng phn t

3. Danh php: c 3 loi tn

a) Tn thay th: axit + v tr + amino + tn axit cacboxylic tng ng.
V d: H2NCH2COOH: axit aminoetanoic HOOC[CH2]2CH(NH2)COOH: axit 2-
aminopentanioic
b) Tn bn h thng: axit + v tr ch ci Hi Lp (, , , , , ) + amino + tn thng thng ca axit cacboxylic tng
ng.
V d: CH3CH(NH2)COOH : axit -aminopropionic H2N[CH2]5COOH : axit -aminocaproic
H2N[CH2]6COOH: axit -aminoenantoic
c) Tn thng thng: cc amino axit thin nhin (-amino axit) u c tn thng.
V d: H2NCH2COOH c tn thng l glyxin (Gly) hay glicocol
Cong thc Ten thay the Ten ban he thong Ten thng K hieu
CH2 -COOH
Axit aminoetanoic Axit aminoaxetic Glyxin Gly
NH2
CH3 - CH - COOH Axit Axit
Alanin Ala
NH2 2 - aminopropanoic - aminopropanoic
CH3 - CH CH -COOH Axit - 2 amino -3 -
Axit - aminoisovaleric Valin Val
CH3 NH 2 metylbutanoic

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HO CH2 CH COOH Axit - 2 - amino -3(4 - Axit - amino -

(p - hiroxiphenyl) propionic Tyrosin Tyr
NH2 hiroxiphenyl)propanoic
HOOC(CH2)2CH - COOH Axit Axit Axit
Glu
NH 2 2 - aminopentanioic 2 - aminopentanioic glutamic
H 2N - (CH2)4 - CH - COOH Axit Axit
Lysin Lys
NH2 2,6 - iaminohexanoic , - iaminocaproic

4. Phn loi
Da vo cu to gc R phn 20 amino axit c bn thnh cc nhm.
Mt trong cc cch phn loi l 20 amino axit c phn thnh 5 nhm nh sau:
a) Nhm 1: cc amino axit c gc R khng phn cc k nc: Gly (G), Ala (A), Val (V), Leu (L), ILe (I), Pro (P)
b) Nhm 2: cc amino axit c gc R l nhn thm: Phe (F), Tyr (Y), Trp (W)
c) Nhm 3: cc amino axit c gc R baz, tch in dng: Lys (K), Arg (R), His (H)
d) Nhm 4: cc amino axit c gc R phn cc, khng tch in: Ser (S), Thr (T), Cys (C), Met (M), Asn (N), Gln (Q)
e) Nhm 5: cc amino axit c gc R axit, tch in m: Asp (D), Glu (E)
II TNH CHT VT L
Cc amino axit l cc cht rn khng mu, v hi ngt, d tan trong nc v chng tn ti dng ion lng cc (mui ni
phn t), nhit nng chy cao (v l hp cht ion)
III TNH CHT HA HC
1. Tnh cht axit baz ca dung dch amino axit
a) Tc dng ln thuc th mu: (H2N)x R (COOH)y.
Khi: - x = y th amino axit trung tnh, qu tm khng i mu
- x > y th amino axit c tnh baz, qu tm ha xanh
- x < y th amino axit c tnh axit, qu tm ha
b) Tnh cht lng tnh:
- Tc dng vi dung dch baz (do c nhm COOH)
H2NCH2COOH + NaOH H2NCH2COONa + H2O
hoc: H3N+CH2COO + NaOH H 2NCH2COONa + H2O
- Tc dng vi dung dch axit (do c nhm NH2)
H2NCH2COOH + HCl ClH 3NCH2COOH
hoc: H3N+CH2COO + HCl ClH3NCH2COOH
2. Phn ng este ha nhm COOH
HCl

H 2 N CH 2 COOH C2 H 5 OH ClH 3 N CH 2 COOC2 H 5 H 2O
3. Phn ng ca nhm NH 2 vi HNO2
H 2NCH2COOH + HNO2 HOCH 2 COOH + N2 + H 2O
axit hiroxiaxetic
4. Phn ng trng ngng
- Do c nhm NH2 v COOH nn amino axit tham gia phn ng trng ngng to thnh polime thuc loi poliamit
- Trong phn ng ny, OH ca nhm COOH phn t axit ny kt hp vi H ca nhm NH2 phn t axit kia to thnh
nc v sinh ra polime
Th du :
... + H - NH -[CH2]5CO- OH + H - NH[CH2]5CO - OH + H - NH - [CH2]5CO -OH +
T
. . . - NH - [CH2]5CO - NH - [CH2]5CO - NH -[CH2]5CO - ... + nH2O
Hay vet gon la :
T
n H2N[CH2]5COOH (- HN[CH2]5CO -)n + n H2O

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 TI LIU LUYN THI & BI DNG KIN THC NM 2011

V - NG DNG
- Amino axit thin nhin (hu ht l -amino axit) l c s kin to nn cc loi protein ca c th sng
- Mui mononatri ca axit glutamic c dng lm m chnh (hay bt ngt)
- Axit -aminocaproic v axit -aminoenantoic l nguyn liu sn xut t tng hp (nilon 6 v nilon 7)
- Axit glutamic l thuc h tr thn kinh, methionin (CH3SCH2CH2CH(NH2)COOH) l thuc b gan
III. PEPTIT
I KHI NIM V PHN LOI
1. Khi nim
Lin kt ca nhm CO vi nhm NH gia hai n v -amino axit c loi l lin kt peptit
C N
O H
Peptit l nhng hp cht cha t 2 n 50 gc -amino axit lin kt vi nhau bng cc lin kt petit
Th du : ipeptit glyxylalanin H2N CH2 CO NH CH COOH
CH 3
Lien ket peptit
2. Phn loi
Cc peptit c phn thnh hai loi:
a) Oligopeptit: gm cc peptit c t 2 n 10 gc -amino axit v c gi tng ng l ipeptit, tripeptit
b) Polipeptit: gm cc peptit c t 11 n 50 gc -amino axit. Polipeptit l c s to nn protein
II CU TO, NG PHN V DANH PHP
1. Cu to v ng nhn
- Phan t peptit hp thanh t cac goc - amino axit noi vi nhau bi lien ket peptit theo mot trat t nhat nh :
amino axit au N con nhom NH2, amino axit au C cua nhom COOH.
H2N CH CO NH CH CO NH CH CO .... NH CH COOH
R1 R2 R3 Rn
au N - Lien ket peptit - au C
- Nu phn t peptit cha n gc -amino axit khc nhau th s ng phn loi peptit s l n!
H2N CH2 CO NH CH COOH ; H2N CH CO NH CH2 COOH
CH3 CH 3
n!
- Nu trong phn t peptit c i cp gc -amino axit ging nhau th s ng phn ch cn
2i
2. Danh php
Tn ca peptit c hnh thnh bng cch ghp tn gc axyl ca cc -amino axit bt u t u N, ri kt thc bng tn
ca axit u C (c gi nguyn).
Th du : H2NCH2CO NH-CHCO - NH - CH - COOH
CH3 CH(CH3)2
Glyxylalanylvanin(Gly-Ala-Val)
III TNH CHT
1. Tnh cht vt l
Cc peptit thng th rn, c nhit nng chy cao v d tan trong nc
2. Tnh cht ha hc
a) Phn ng mu biure:
- Da vo phn ng mu ca biure: H2NCONHCONH2 + Cu(OH)2 phc cht mu tm c trng
- Amino axit v ipeptit khng cho phn ng ny. Cc tripeptit tr ln tc dng vi Cu(OH)2 to phc cht mu tm
b) Phn ng thy phn:
- iu kin thy phn: xc tc axit hoc kim v un nng
- Sn phm: cc -amino axit
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B PROTEIN
I KHI NIM V PHN LOI
Protein l nhng polipeptit cao phn t c phn t khi t vi chc nghn n vi triu. Protein c phn thnh 2 loi:
- Protein n gin: c to thnh ch t cc -amino axit
- Protein phc tp: c to thnh t cc protein n gin kt hp vi cc phn t khng phi protein (phi protein) nh
axit nucleic, lipit, cacbohirat
II TNH CHT CA PROTEIN
1. Tnh cht vt l
a) Hnh dng:
- Dng si: nh keratin (trong tc), miozin (trong c), fibroin (trong t tm)
- Dng cu: nh anbumin (trong lng trng trng), hemoglobin (trong mu)
b) Tnh tan trong nc: Protein hnh si khng tan, protein hnh cu tan
c) S ng t: L s ng li ca protein v tch ra khi dung dch khi un nng hoc thm axit, baz, mui
2. Tnh cht ha hc
a) Phn ng thy phn:
- iu kin thy phn: xc tc axit hoc kim v un nng hoc xc tc enzim
- Sn phm: cc -amino axit
b) Phn ng mu:
Anbumin (Protein c trong long trng trng0
HNO3 c Kt ta mu vng (do sn phm c nhm NO2)
Cu(OH)2 Phc cht mu tm c trng (phn ng biure)
III KHI NIM V ENZIM V AXIT NUCLEIC
1. Enzim
Hu ht c bn cht l protein, xc tc cho cc qu trnh ha hc c bit l trong c th sinh vt. Enzim c gi l cht
xc tc sinh hc v c c im:
- Tnh chn lc (c hiu) cao: mi enzim ch xc tc cho mt phn ng nht nh
- Hot tnh cao: tc phn ng nh xc tc enzim rt cao, gp 109 1011 cht xc tc ha hc
2. Axit nucleic
Axit nucleic l mt polieste ca axit photphoric v pentoz
+ Nu pentoz l riboz, axit nucleic k hiu ARN
+ Nu pentoz l eoxiriboz, axit nucleic k hiu ADN
+ Phn t khi ADN t 4 8 triu, thng tn ti dng xon kp
+ Phn t khi ARN nh hn ADN, thng tn ti dng xon n

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MT S CH KHI GII BI TP

1. Mt s dng bi tp hay hi:

a) So snh lc baz ca cc amin
b) m ng phn amin, amino axit, peptit
c) Xc nh cng thc phn t amin, amino axit theo phn ng chy
d) Xc nh cng thc phn t amin theo phn ng vi dung dch axit hay dung dch mui
e) Xc nh cng thc phn t amino axit theo phn ng axit baz
f) Xc nh cng thc cu to ca hp cht
g) Phn bit tch cc cht

2. Mt s cng thc hay dng:

a) Cng thc phn t ca amin:
- Amin n chc: CxHyN (y 2x + 3)
- Amin n chc no: CnH2n + 1NH2 hay CnH2n + 3N
- Amin a chc: CxHyNt (y 2x + 2 + t)
- Amin a chc no: CnH2n + 2 z(NH2)z hay CnH2n + 2 + zNz
- Amin thm (ng ng ca anilin): CnH2n 5N (n 6)
b) Cng thc phn t CxHyO2N c cc ng phn cu to mch h thng gp:
- Amino axit H2NRCOOH
- Este ca amino axit H2NRCOOR
- Mui amoni ca axit ankanoic RCOONH4 v RCOOH3NR
- Hp cht nitro RNO2
c) Cng thc hay dng:
2x 2 t y
- Cng thc bt bo ha (s lin kt + v) ca CxHyNt: =
2
2x 2 t y
- Cng thc bt bo ha (s lin kt + v) ca CxHyOzNt: =
2
Ch : Cng thc ch ng khi gi thit tt c cc lin kt u l lin kt cng ha tr, i vi hp cht ion th cng thc
khng cn ng na.
2.2 2 1 7
V d CH3COONH4 c = 0 nhng trong CH3COONH4 lun 1 lin kt (bi y l hp cht lk ion)
2
- Nu phn t peptit cha n gc -amino axit khc nhau th s ng phn loi peptit s l n!
n!
- Nu trong phn t peptit c i cp gc -amino axit ging nhau th s ng phn ch cn
2i
3. Mt s phn ng cn lu
3CnH2n + 3N + FeCl3 + 3H2O Fe(OH)3 + 3CnH2n + 4NCl
(H2N)x R(COOH)y + xHCl (ClH3N)x R(COOH)y
(ClH3N)x R(COOH)y + (x + y)NaOH (H2N)x R(COONa)y + xNaCl + (x + y)H2O
(H2N)x R(COOH)y + yNaOH (H 2N)x R(COONa)y + yH2O
(H2N)x R(COONa)y + (x + y)HCl (ClH3N)x R(COOH)y + yNaCl
2(H2N)x R(COOH)y + xH2SO4 [(H3N)x R(COOH)y]2(SO4)n
2(H2N)x R(COOH)y + yBa(OH)2 [(H2N)x R(COO)y]2Bay + 2 yH2O
Tng hp/bin son : Thy Ng Xun Qunh

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