CHUYN : ESTE V LIPIT

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CU TO, DANH PHP, TNH CHT, IU CH, NG DNG

I. CU TO PHN T
1. Khi nim
Este l sn phm ca phn ng este ho gia axit hu c (este hu c) hoc axit v c (este v c) vi ru.

Khi thay nhm OH nhm cacboxyl ca axit cacboxylic bng nhm OR' th c este.
H

R COO R ' HOH

R CO OH H O R '
Este n gin c cng thc cu to nh sau :
Gc R l: H hoc cha nguyn t Cacbon
R C O R'
Gc R' l: Bt buc phi cha nguyn t Cacbon
O
2. ng phn:
Este no, n chc, mch h: CnH2nO2 n 2 hay R-COO-R'
+ Bc 1:
Chn R l H
+ Bc 2:
Dn s nguyn t Cacbon sang bn R'
Nu s C trong R' 3 => xut hin dng mch Cacbon (mch thng; mch nhnh)
+ Bc 3:
Tng s Cacbon bn pha R (chuyn C t R' qua R)
Nu s C trong R 3 => xut hin dng mch Cacbon (mch thng; mch nhnh)
O C C C C
O C C
C
C
O C

O C
C

O C

C
* Nu nh trong phn t Este c cha lin kt i, th ta cn ch quan tm ti v tr ca lin kt i trong
dng mch Cacbon v ng phn hnh hc (ng phn cis trans)
V d: Vit cng thc cc ng phn ca este sau:
a. C4H8O2
b. C3H6O2
c. C3H4O2
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d. C4H6O2
e. C7H6O2 (c vng benzen)
f. C8H8O2 (c vng benzen)
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II. DANH PHP
Tn este gm: tn gc hirocacbon R' + tn anion gc axit (ui "at").
* Tn mt s axit cn ghi nh:
* Tn gc ankyl (phn R')
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Bin son ging dy: Thy Ng Xun Qunh T: 0979.817.885 E_mail: admin@hoahoc.org - http://www.hoahoc.org

Mi bi tp khng ch n gin l tnh ton, ng sau l nhng tng

III. TNH CHT VT L

+ tso Axit tso Ancol tso Este tso Hidrocacbon (Do este khng c cha lin kt hidro trong phn t)
+ Cc este thng l nhng cht lng, nh hn nc, rt t tan trong nc, c kh nng ho tan c nhiu cht
hu c khc nhau. Nhng este c khi lng phn t rt ln c th trng thi rn (nh m ng vt, sp
ong,...).
+ Cc este thng c mi thm d chu, chng hn :
isoamyl axetat CH3COO-CH2CH2CH(CH3)2 c mi chui chn.
benzyl propionat CH3-CH2-COO-CH2C6H5 : c mi hoa nhi.
etyl butirat CH3-CH2-CH2-COO-C2H5 c mi da.
etyl isovalerat : CH3-CH2-CH2-CH2-COOC2H5 : c mi to.
V d:
a. Hy sp xp chiu tng dn nhit si ca cc cht sau: Etanol; axit axetic; Etan; metyl fomat
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IV.TNH CHT HA HC
a. Phn ng nhm chc
Phn ng thu phn :
Tnh cht ho hc quan trng nht ca este l phn ng thu phn (phn ng vi nc). Trong qu trnh thu
phn c thc hin trong dung dich axit hoc baz.
Trong dung dch axit:
H

R COOH + R ' OH
R COO R ' H 2O
Phn ng theo chiu t tri sang phi l phn ng thu phn este, phn ng theo chiu t phi sang tri l phn
ng este ho.
Vy phn ng thu phn este trong dung dich axit l phn ng thun nghch.
H

R COONa + R ' OH
Trong dung dich baz: R COO R ' NaOH
V d: Vit cc phng trnh phn ng khi cho: Metyl axetat; Etyl axetat, Etyl fomat; vinyl axetat, metyl
acrylat; metyl benzonat, phenyl axetat tc dng ln lt vi NaOH.
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* Mt s trng hp lu : Phn ng thy phn este c 4 trng hp xy ra
+ Trng hp 1: to Ancol v mui
H

R COONa + R ' OH
R COO R ' NaOH
+ Trng hp 2: to Andehit v mui
R COO-CH=CH R '

R COONa + R ' CH 2 CHO

NaOH

+ Trng hp 3: to hai mui

R COO C6 H6 x - R x

R COONa + R ' OH
NaOH

+ Trng hp 4: to Xeton v mui

R COO-C(CH3 ) CH R '

R COONa + R ' CH 2 CO CH 3
NaOH

Mi li gii khng ch l p dng phng php m thc s l mt qu trnh phn tch v sng to

CHUYN : ESTE V LIPIT

-3-

b. Phn ng gc hirocacbon
Este c th tham gia phn ng th, cng, tch, trng hp,
Sau y ch xt phn ng cng v phn ng trng hp.
- Phn ng cng vo gc khng no: Gc hirocacbon khng no este c phn ng cng vi H 2, Br2, Cl2...
ging nh hirocacbon khng no.
Th d : Cho vinyl axetat tc dng vi H2 t 0 , Ni
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t0
CH3[CH2]7CH=CH[CH2]7COOCH3 + H2
CH3[CH2]16COOCH
Ni
Metyl oleat
Metyl stearat
- Phn ng trng hp: Mt s este n gin c lin kt C = C tham gia phn ng trng hp ging nh anken.
Th d : Trng hp cc cht: Vinyl axetat; Metyl acrylat; metyl metacrylat
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c. Phn ng chy
Este n chc chy m: nCO2 nH2O
Este NO, N CHC
CTTQ: CnH2nO2 n 2

3n 2
t0
O2
nCO2 nH 2O
2
V d: t chy este khng no, n chc v mt lin kt
CTPT: .......................................................................................................................................................................
Phn ng chy:..........................................................................................................................................................
Nhn xt: ..................................................................................................................................................................
V.IU CH
1. Este ca ancol
Phng php thng dng iu ch este ca ancol l un hi lu ancol vi axit hu c, c H 2SO4 c xc
tc, gi l phn ng este ho. Th d :
Cn H 2 nO2

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Phn ng este ho l phn ng thun nghch. nng cao hiu sut ca phn ng c th ly d mt trong hai
cht u hoc lm gim nng cc sn phm. Axit sunfuric va lm xc tc va c tc dng ht nc, do
gp phn lm tng hiu sut to este.
2. Este ca phenol:
iu ch este ca phenol khng dng axit cacboxylic m phi dng anhirit axit hoc clorua axit tc dng
vi phenol. Th d :

CH3COOC6H5 + CH3COOH
C6H5OH + (CH3CO)2O
Andehit axetic
Phenyl axetat
CH3COOH CH CH
CH3COO CH CH 2
3. Este khng no:
VI. NG DNG
- Lm dung mi (butyl v amyl axetat c dng pha sn tng hp)
- Poli(metyl acrylat), poli(metyl metacrylat) dng lm thy tinh hu c, poli(vinyl axetat) dng lm cht do
hoc thy phn thnh poli(vinyl ancol) dng lm keo dn
- Mt s este c mi thm ca hoa qu c dng trong cng nghip thc phm (bnh ko, nc gii kht) v
m phm (x phng, nc hoa)
Bin son ging dy: Thy Ng Xun Qunh T: 0979.817.885 E_mail: admin@hoahoc.org - http://www.hoahoc.org

Mi bi tp khng ch n gin l tnh ton, ng sau l nhng tng

B. LIPIT
I PHN LOI, KHI NIM V TRNG THI T NHIN
1. Phn loi lipit
- Lipit l nhng hp cht hu c c trong t bo sng, khng ha tan trong nc nhng tan trong cc dung mi
hu c khng phn cc nh t, clorofom, xng du
- Lipit c chia lm hai loi: lipit n gin v lipit phc tp.
+ Lipit n gin: sp, triglixerit v steroit
+ Lipit phc tp: photpholipit
Sp: - Este ca monoancol phn t khi ln vi axit bo phn t khi ln
- L cht rn iu kin thng (sp ong)
Steroit: - Este ca axit bo c phn t khi ln vi monoancol a vng c phn t khi ln (gi l sterol)
- L cht rn khng mu, khng tan trong nc
Photpholipit : - Este hn tp ca glixerol vi axit bo c phn t khi cao v axit photphoric
- V d: lexithin (trong lng trng g)
2. Khi nim cht bo
- Cht bo l trieste ca glyxerol vi cc axit monocacboxylic c s chn nguyn t C (thng t 12C n 24C)
khng phn nhnh, gi chung l triglixerit.
- Khi thy phn cht bo th thu c glyxerol v axit bo (hoc mui)
- Cht bo c cng thc chung l:

(R1, R2, R3 l cc gc hirocacbon no hoc khng no, khng phn nhnh, c th ging nhau hoc khc nhau)
- Axit bo no thng gp l:
C15H31COOH (axit panmitic, tnc = 63oC)
C17H35COOH (axit stearic, tnc = 70oC)
- Axit bo khng no thng gp l:
C17H33COOH (axit oleic, tnc = 13oC)
C17H31COOH (axit linoleic, tnc = 5oC)
- Tristearin (glixeryl tristearat) c tnc = 71,5oC
Tripanmitin (glixeryl panmitat) c tnc = 65,5oC
Triolein (glixeryl trioleat) c tnc = - 5,5oC
* Tn gi ca cht bo: Trong trng hp cc gc hidrocacbon ca axit bo ging nhau, tn ca cht bo c th
c gi tn mt cch n gin nh sau:
Tn cht bo = Tri + tn thng thng ca axit (i ui "IC" thnh ui "IN"
V d: (C17H33COO)3C3H5
Triolein (lng)
(C17H33COO)3C3H5
Tristearin (rn)
3. Trng thi t nhin
II TNH CHT CA CHT BO
1. Tnh cht vt l
- R1, R2, R3: Ch yu l gc hirocacbon no th cht bo l cht rn.
- R1, R2, R3: Ch yu l gc hirocacbon khng no th cht bo l cht lng.
Khng tan trong nc nhng tan nhiu trong cc dung mi hu c khng cc: benzen, clorofom,
Nh hn nc, khng tan trong nc.
- Cc cht bo khng tan trong nc do gc hirocacbon ln ca cc axit bo lm tng tnh k nc ca cc
phn t cht bo
- Du thc vt thng c hm lng axit bo cha no (u dng cis) cao hn m ng vt lm cho nhit
nng chy ca du thc vt thp hn so vi m ng vt. Thc t, m ng vt hu nh tn ti trng thi rn
cn du thc vt tn ti trng thi lng
Mi li gii khng ch l p dng phng php m thc s l mt qu trnh phn tch v sng to

CHUYN : ESTE V LIPIT

-5-

2. Tnh cht ha hc
a) Phn ng thy phn trong mi trng axit:

Triglixerit
b) Phn ng x phng ha:

Glixerol

Axit bo

Triglixerit
Glixerol
X phng
- Khi un nng cht bo vi dung dch kim th to ra glixerol v hn hp mui ca cc axit bo. Mui natri
(hoc kali) ca axit bo chnh l x phng
- Phn ng x phng ha xy ra nhanh hn phn ng thy phn trong mi trng axit v khng thun nghch
c) Phn ng hiro ha:

Triolein (lng)
Tristearin (rn)
Phn ng hiro ha cht bo lm tng nhit nng chy ca cht bo
d) Phn ng oxi ha:
Ni i C=C gc axit khng no ca cht bo b ox ha chm bi oxi khng kh to thnh peoxit, cht ny b
phn hy thnh anehit c mi kh chu. l nguyn nhn ca hin tng du m b i thiu
II VAI TR CA CHT BO
1. S chuyn ha ca cht bo trong c th

2. ng dng
- Thc n cho ngi, l ngun dinh dng quan trng v cung cp phn ln nng lng cho c th hot ng.
- L nguyn liu tng hp mt s cht khc cn thit cho c th. Bo m s vn chuyn v hp th c
cc cht ho tan c trong cht bo.
- Trong cng nghip, mt lng ln cht bo dng sn xut x phng v glixerol. Sn xut mt s thc
phm khc nh m si, hp,
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Mi bi tp khng ch n gin l tnh ton, ng sau l nhng tng

C. CHT GIT RA
I KHI NIM V TNH CHT CA CHT GIT RA
1. Khi nim cht git ra
- L nhng cht khi dng cng vi nc th c tc dng lm sch cc cht bn bm trn cc vt rn m khng
gy ra phn ng ha hc vi cc cht
- Cc cht git ra ly trc tip t thin nhin nh b kt, b hn,v cc cht git ra tng hp
2. Tnh cht git ra
a) Mt s khi nim lin quan:
- Cht ty mu lm sch cc vt bn nh nhng phn ng ha hc nh nc Gia-ven, nc clo
- Cht u nc l cht tan tt trong nc nh etanol, axit axetic,
- Cht k nc l nhng cht hu nh khng tan trong nc nh hirocacbon, dn xut halogen. Cht k nc
th a du m, tc tan tt vo du m. Cht u nc th thng k du m
b) c im cu trc phn t mui natri ca axit bo:

(Cng thc cu to gn nht ca phn t mui natri stearat)

- Gm u a nc l nhm COO Na+ ni vi mt ui k nc, a du m l nhm CxHy (thng x 15)
- Cu trc ha hc gm mt u a nc gn vi mt ui di a du m l hnh mu chung cho phn t cht
git ra
c) C ch hot ng ca cht git ra:
Ly trng hp natri stearat lm v d, ui a du m CH3[CH2]16 thm nhp vo vt bn, cn nhm COO
Na+ a nc li c xu hng ko ra pha cc phn t nc. Kt qu l vt bn b chia thnh nhng ht rt nh
c gi cht bi cc phn t natri stearat, khng bm vo vt rn na m phn tn vo nc ri b ra tri i.
II X PHNG V CHT GIT RA TNG HP
X phng

Ging nhau

Cht git ra tng hp

Cng kiu cu trc, ui di khng phn cc a du m kt hp vi u phn cc a nc

ui di khng phn cc a du m
u phn cc a nc
C17H35
COO Na+
Natri stearat C17H35COONa (trong x phng)
C12H25
OSO3 Na+

Natri lauryl sunfat C12H25OSO3Na (trong cht git ra)

- ui l gc hirocacbon ca axit bo, - ui l bt k gc hirocacbon di no, u c th
u l anion cacboxylat
l anion cacboxylat, sunfat
2+
2+
Khi
gp
Ca
,
Mg
trong
nc
cng
th
- Natri lauryl sunfat khng c hin tng nn c
Khc nhau
natri stearat cho kt ta lm gim cht u im l dng c vi nc cng
lng x phng
- un du thc vt hoc m ng vt vi Oxi ha parafin c axit cacboxylic, hiro ha
xt hoc KOH nhit v p xut cao
axit thu c ancol, cho ancol phn ng vi H2SO4
Phng
- Oxi ha parafin ca du m nh oxi ri trung ha th c cht git ra loi ankyl
php sn
khng kh, c xc tc, ri trung ha axit sunfat
xut
sinh ra bng NaOH:
- Cc mui natri (hoc kali) ca axit bo, -Ngoi cht git ra tng hp, cht thm, cht mu,
thng l natri stearat (C17H35COONa), cn c th c cht ty trng nh natri hipoclorit
Thnh phn natri panmitat (C15H31COONa), natri
oleat (C17H33COONa)
chnh
- Cc ph gia thng l cht mu, cht - Natri hipoclorit c hi cho da khi git bng tay
thm

Mi li gii khng ch l p dng phng php m thc s l mt qu trnh phn tch v sng to