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Culture Documents
1. Mt s c im ca cc hp cht hu c: ....................................................................04
2. Gc Hidrocacbon- Nhm th- Nhm chc. ....................................................................04
2.1 Gc hirocacbon ........................................................................................................04
2.2 Nhm th ....................................................................................................................04
2.3 Cacboncation ..............................................................................................................04
2.4 ng ng ..................................................................................................................04
2.5 ng phn ..................................................................................................................04
Cch xc nh ng phn cis-trans ...........................................................................05
Cch vit ng phn ng vi cng thc phn t ......................................................06
3. Mt s gc hidrocacbon v gi tn cn ch : ................................................................07
4. Hiu ng cm ...................................................................................................................08
4.1 Khi nim ...................................................................................................................08
4.2 ng dng .....................................................................................................................08
4.2.1
Dng hiu ng cm so snh mnh yu ca cc axit hu c ..................09
4.2.2
Dng hiu ng cm so snh mnh yu ca cc baz hu c. ...............09
4.2.3
D on sn phm phn ng- kh nng phn ng. .........................................09
5. Cc loi phn ng chnh trong ha hu c. ...................................................................10
5.1 Phn ng th ................................................................................................................10
5.2 Phn ng cng .............................................................................................................10
5.3 Phn ng tch ..............................................................................................................11
5.4 Phn ng oxi ha .........................................................................................................11
5.5 Bng So snh v phn bit mt s phn ng thng gp trong hu c .........................11
6. Hp cht hu c c nhm chc. .....................................................................................12
6.1 Phn loi HCHC c nhm chc. ...............................................................................12
6.2 Bng cng thc tng qut mt s HCHC quan trng ..............................................12
6.3 Bng cc dy ng ng thng gp ng vi CTTQ ( cng thc tng qut ). .......13
6.4 Ha tnh ca mt s cht hu c cn ch : .............................................................13
6.4.1
Ru ................................................................................................................13
6.4.2
Phenol ..............................................................................................................15
6.4.3
Andehit ............................................................................................................16
6.4.4
Xeton ...............................................................................................................17
6.4.5
Axit Cacboxylic ..............................................................................................18
6.5 Cc phng php chnh iu ch mt s cht hu c quan trng: .........................19
6.5.1
Ru ................................................................................................................19
6.5.2
Phenol ..............................................................................................................20
6.5.3
Andehit ............................................................................................................20
6.5.4
Xeton ...............................................................................................................21
6.5.5
Axit cacboxylic ................................................................................................21
BI TP
........................................................................................................................34
1. Mt s c im ca cc hp cht hu c:
-a s HCHC (hp cht hu c) c lin kt cng ha tr ( cn hp cht v c phn ln l lin kt ion).
-Phn ln HCHC khng bn nhit, bay hi, d chy, thng khng tan trong nc.
-Tc phn ng gia cc HCHC thng rt chm v theo nhiu hng khc nhau nn to thnh hn hp
cc sn phm v thng phi dng xc tc.
*Bn cht s gp chung electron trong lin kt cng ha tr ca HCHC:
-Bn cht ca s gp chung eltectron trong lin kt cng ha tr l s xen ph nhng obitan (xem sch gio
khoa lp 10) gia hai nguyn t t th nng cc tiu.
C hai kiu xen ph:
+Kiu xen ph trc: S xen ph ny xy ra trn trc ni
gia hai ht nhn nguyn t.Lin kt cng ha tr hnh
thnh bng cch xen ph trc gi l lin kt (xch ma).
2x 2 ( y u t )
2
CxHy
CxHyO
CxHyOz
CxHyNt
Ankan
Ru no, n
chc, Ete no, n
chc
Ru no, 2 chc
este + ru
Amin no
Anken xicloanken
Andehit, xeton,
ru, ete cha no
Axit. Este,
Andehit+Ru,
andehit+este
Amin khng no
Ankin, ankadien,
xicloanken
Andehit, xeton c
cha ( C=C)
Benzen dn xut
ca halogen
Benzen c 1 lin
kt (C=C) ngoi
vng.
Amin thm
Xc nh nhm chc (c th c) :
-Da vo cng thc phn t, gi tr c th suy ra cc nhm chc c th c.
V d: Vi hp cht CxHyOzNt nu >0 th:
= tng s lin kt v dng mch vng m HCHC c th c.
Cc lin kt c th thuc ( C=C); (-C C-); (C=O); (C=N-); (-N=O), t suy ra c nhm nh chc
v s ni a trong HCHC.
-Bc 2: Vit mch cacbon c th c, t mch di nht ( mch thng) n mch chnh ngn nht, bng cch
bt dn s nguyn t cacbon mch chnh to nhnh ( gc ankyl).
-Bc 3: Thm ni a(i, ba), nhm chc, nhm th vo cc v tr thch hp trn tng mch cacbon.
-Bc 4: Bo ha gi tr cacbon bng s nguyn t Hidro sao cho .
3. Mt s gc hidrocacbon v gi tn cn ch :
Gc
No
Khng no
Thm
Cu to
Gi tn
CH3CH2CH2-
n-propyl
CH3-CH|
CH3
CH3CH2CH|
CH3
CH3
|
CH3 C
|
CH3
CH3
|
CH3 C CH2
|
CH3
CH2=CH-
CH3-CH=CHCH2=C
|
CH3
C6 H 5 -
Propenyl
Iso- propenyl
Phenyl
C6H5 CH2
CH3 C6H4
Benzyl
p-Tolyl
Neo-pentyl
Vinyl
4. Hiu ng cm
4.1 Khi nim.
Hiu ng cm (I) l s phn cc ca lin kt gy nn s do s chnh lch v m in ca 2 nguyn
t hay 2 nhm nguyn t to nhm lin kt. ( ni cch khc hiu ng cm l s dch chuyn cp electron
trong ni n do nhm th X ht hay y cp electron ).
Hiu ng cm c biu din bng
hng theo chiu di chuyn ca i in t dng chung.
V d:
CH 3 OH
C2 H 5 OH
H OH
Cl CH COOH
Cl
CH 3 NH 2
C2 H 5 NH 2
H NH 2
CH 3 NH CH 3
CH 3 COOH
Cl CH 2 COOH
tr
xem
C
R C O H
, do s c mt ca nhm cacbonyl || nn lin kt O- H vn
O
O
phn cc tr nn phn cc rt mnh. Kt qu l phn t RCOOH d dng phng thch H+, th hin tnh axit.
Axit hu c cng mnh th n phng thch H+ cng d. iu ny xy ra khi trn R c cc nhm th gy
hiu ng cm m.
V d: So snh tnh axit ca ru etylic vi nc:
Trong phn t ru etylic v nc xy ra cc hiu ng cm
C2 H 5
O H
H
O H
Kt qu l lin kt O H trong nc linh ng hn trong ru nn nc c tnh axit mnh hn ru.
V d 2: So snh tnh axit ca:
a) axit fomic; axit axetix; axit propionic
b) axit axetic; axit monoclo axetic; axit iclo axetic.
a. Trong phn t axit trn xy ra cc hiu ng cm :
CH 3 C O H
||
O
H C O H
||
O
C2 H 5 C O H
||
O
Kt qu l lin kt O H trong axit formic linh ng nht, ri n axit axetic v axit propionic. Vy tnh
axit ca axit formic > axit axetix> axit propionic.
b. Trong cc phn t axit trn xy ra hiu ng cm:
CH 3 C O H
||
O
Cl CH 2 C O H
||
O
Cl CH C O H
||
Cl O
Kt qu l lin kt O H trong axit iclo axetic linh ng nht ri n axit monoclo axetic v n axit
axetic. Do tnh axit ca axit iclo axetic > axit monoclo axetic > axit axetic.
4.2.2 Dng hiu ng cm so snh mnh yu ca cc baz hu c.
Cc amin u c tnh baz.
Tnh baz cng mnh th kh nng thu nhn H+ cng d. iu ny xy ra khi cc gc R gn trn nguyn
t N ca amin l cc gc gy hiu ng cm dng mnh.
V d: So snh tnh baz ca metylamin vi amoniac v imetylamin.
Trong cc phn t amin trn xy ra cc hiu ng cm:
CH 3 NH 2
(I)
H NH 2
(II)
CH3 NH CH 3
(III)
Tn Ankan
CH4+Cl2
Aren
Ankin
CH3Cl +HCl
C ch gc t do
+HBr
+ Br2
C ch ion
HC CH + 2 AgNO3+3 NH3
Ag C C Ag
+2NH4NO3+NH3
Th ion kim loi
10
CH 2 CH CH 3
|
|
Cl
H
( sp Chnh)
CH2=CH CH3 + HCl
CH 2 CH CH 3
|
|
Cl
H
(Sp Phu.)
OH
H
|
|
CH 2 C CH 3
|
CH
3
CH 2 C CH 3 HOH ( Sp chnh)
|
;
CH 3
H
OH
|
|
CH C CH
2
3
CH
(sp phu. ) 3
H2C=CH2 + H2O
Trng ngng
-Qu trnh nhiu phn t nh (monome) kt hp vi
nhau thnh phn t ln (polime) ng thi gii phng
nhng phn t c khi lng nh (nh H2O, NH3,
HCl,) c gi l phn ng trng ngng.
-c im cu to cc monome tham gia phn ng
trng ngng l phi c t hai nhm chc tr ln.
V d: H2N CH2 COOH ;
H2N (CH2)6 NH2
;
HOOC (CH2)4 COOH ;
H2N (CH2)5 COOH
;
11
( HN CH 2 C )n + nH 2 O
||
O
Hyrat ha
-Cht phn ng c lin kt cn tc nhn l H2O.
-Phn ng xy ra 1 chiu.
V d:
CH2=CH2 +H2O CH3 CH2 OH
X phng ha
-L phn ng thy phn este ca axit hu c trong
mi trng kim (NaOH, KOH, ) to mui
ca axit cacboxylic.
-Phn ng mt chiu.
RCOOR +H2O
ROH+RCOONa +H2O
Thy phn
-Cht phn ng l este, ete, dn xut halogen ca
CxHY, cn tc nhn l nc.
-Phn ng thun nghch.
V d:
CH3Cl+H2O CH3OH + HCl
Thy phn
-Cht phn ng l este, ete, dn xut halogen ca
CxHY, cn tc nhn l nc.
-Phn ng thun nghch.
V d:
CH3Cl+H2O CH3OH + HCl
R(CHO)x
CnH2n+2-x(CHO)x
R CHO hay CxHyCHO
CnH2n+1CHO hay CmH2mO
R COOH hay CxHyCOOH
12
iu kin
y 2x +2
y 2x +2 +t
y 2x +2 u
x,n 1
x 1, y 2x+1
x 0, y 2x+1
n1
n0
x
x
x
n
x
1
1, n 0
0, y 2x+1
0, m 1
0, y 2x+1
i axit no
CnH2n(COOH)2
Axit n chc, no
CnH2n+1COOH hay CmH2mO2
Este n chc
R COO R
Este n chc, no
CnH2nO2
Amin n chc
CnHyN
Amin n ch, no
CnH2n+3N
CnH2n+1 NH2
Amin bc I, no, n chc
iu kin chung: x, y, z, t, u, n, m u N
(R ) l gc hidrocacbon no hay khng no
n0
n 0, m 1
R H
n2
y 2x+3
n1
n1
V d:
( Ru benzylic)
( p-Crezol)
Ru thm c phn ng th trn gc (C6H5-):
13
+Ancol hu nh khng phn ng c vi NaOH, m ngc li, natri ancolat ( RO Na) b thy phn
hon ton:
RO Na +H OH RO H +NaOH
Natri etylat
* Tc dng vi Cu(OH)2: Ch phn ng vi ru a chc c t nht 2 nhm OH k nhau cho dung dch
c mu xanh lam.
CH 2 OH HO CH 2
|
|
2CH 2 CH CH 2 Cu (OH )2 CH O Cu O CH 2 H 2O
|
|
|
|
|
OH OH OH
CH 2 OH HO CH 2
*Tch nc to lin kt .
Khi un nng vi H2SO4 c 1700C, c mi phn t ancol tch 1 phn t nc to thnh 1 phn t
Anken.
14
*Este ha:
Axit + Ru
Este +H2O
(RCOOH + ROH
RCOO R + H2O)
*Oxi ha:
+Ru bc (I) b oxi ha cho andehit.
RCH2OH +CuO
RCHO +Cu +H2O
+Ru bc (II) b oxi ha cho xeton.
R C R ' Cu H 2 O
||
O
R CH R '
|
+CuO
OH
R CH =CH2 +H2O
R CH CH 3
|
OH
R CH =CH2 +H2O
* Phn ng c bit:
M gO ,Zn
2 C2H5OH
to
Phenolat natri
+Tc dng vi NaOH.
Nn:
Ngc li:
R C OH
||
O
+H2O +CO2
+NaHCO3
6.4.3 Andehit:
-Andehit l nhng hp cht hu c m trong phn t c nhm (CH=O) lin kt trc tip vi nguyn t
cacbon hoc Hiro. Nhm CH=O c gi l nhm chc ca andehit, n c gi l nhm cacbanehit.
Vd: HCH=O ( fomandehit); CH3CH=O( axetandehit)
*Phn ng cng H2( phn ng kh):
Khi c xc tc Ni un nng, andehit cng vi hiro to ra ancol bc I:
RCHO +H2
CH3CH=O + H2
RCH2OH
CH3CH2 OH
16
6.4.4 Xeton.
-Xeton l hp cht hu c m phn t c nhm >C=O lin kt trc tip vi hai nguyn t cacbon
V d: H3C CO CH3
*Xeton cng tham gia phn ng cng hiro khi c mt Ni xc tc, un nng to thnh ancol bc (II):
17
CH 3 CH CH 3
|
OH
*Phn ng gc hirocacbon
Nguyn t hiro bn cnh nhm cacbonyl d tham gia phn ng.
V d:
[ H 3O ][ RCOO ]
[ RCOOH ]
OOC COO 2 H 2O
\ /
Ca
-Trong cc axit no n chc, axit fomic (HCOOH) mnh hn c. Cc nhm ankyl y electron v pha
nhm cacboxyl nn lm gim lc axit. Cc nguyn t c m in ln gc R ht electron ca nhm
cacboxyl .
*Phn ng vi ancol ( phn ng este ha )
18
*Phn ng th gc no.
Khi dng photpho xc tc, Cl ch th cho H cacbon bn cnh nhm cacboxyl
CH3CH2 CH2COOH +Cl2
*Phn ng th gc thm.
Nhm cacboxyl vng benzen nh hng cho phn ng th tip theo vo v tr meta lm cho phn ng
kh khn hn so vi th vo benzen.
xt, t0, P
CH 2 CH n
|
COOH
enzim
nC6H12O6
enzim
C6H12O6
2C2H5OH + 2CO2
*Hirat ha anken xc tc axit
CnH2n +H2O
H+
CH2=CH2 + H2O
CnH2n+1OH
H2SO4, 3000C
CH3CH2OH
* T andehit v xeton.
R CHO +H2
Ni
R CH2OH ( ru bc I )
19
R CO R
R CHOH R ( Ru bc II)
R Cl +NaOH
R OH +NaCl
t
C2H5Cl + NaOH
C2H5 OH +NaCl
CH 2 CH CH 2 3 NaOH CH 2 CH CH 2 3 NaCl
|
|
|
|
|
|
Cl
Cl Cl
OH OH OH
R COO R + NaOH
R COONa + ROH
+CH4 +H2O
CO + 3H2
CO +2H2
t ,xt,p
CH3OH
t ,xt,p
+ 2CH4 +O2
2CH3 OH
6.5.2 Phenol:
*T C6H6:
CH2=CHCH3 , H+
C6 H 6
Benzen
C6H6 +Cl2
Fe
1)O2(kk); 2)H2SO4
C6H5CH(CH3)2
Cumen (isopropyl benzen)
C6H5Cl +HCl
to, p
C6H5Cl + NaOH
C6H5OH +NaCl
*T natri phenolat:
C6H5ONa +HCl C6H5OH + NaCl
C6H5ONa + CO2 +H2O C6H5OH + NaHCO3
* Oxi ha iso propyl benzen:
6.5.3 Andehit:
*Oxi ha ru bc (I):
R CH2 OH +CuO
CH3OH +CuO
to,
to,
C6H5OH + CH3COCH3
axeton
to,xt
CH4 + O2
HCHO + H2O
*Thy phn dn xut 1,1 ihalogen.
Cl
|
to,
CH 3 CH 2 NaOH
|
Cl
1)O2
2)H2SO4, 20%
HgSO4,to
*C2H2 +H2O
CH3CHO
R C R ' Cu H 2 O
||
O
*T Canxi axetat
(CH3COO)2Ca
to,
Hoc t CH3COONa:
2CH3COONa
to,
H O+
4
2
C6H5 CH3
C6H5COOK 3
C6H5 COOH
+Oxi ha ru bc I tng ng:
5CH2 CH2OH + 4KMnO4 + 6H2SO4 5CH3COOH + 2K2SO4+4MnSO4+11H2O
+Oxi ha hirocacbon cha no:
5CH3 CH = CH CH3 +8KMnO4+12H2SO4 10CH3COOH + 4K2SO4+8MnSO4 +12H2O
+Oxi ha ankan thch hp:
[O], xt. t0
R CH3
RCOOH +H2O
21
*T dn xut halogen:
H O+,t0
KCN
R X
R C N 3
R COOH
+Thy phn dn xut 1,1,1 trihalogen.
Cl
|
t0
CH 3 C Cl 3 NaOH
|
Cl
CH3COOH +H2O
CH3CH=O + O2
CH3COOH
OHC CHO + O2
t , xt
HOOC COOH
*T metanol
to, xt
CH3OH +CO
CH3COOH
*T mui natri ca axit cacboxylic:
R COONa +H2SO4() R COOH +NaHSO4
7. Hp cht hu c tp chc.
7.1. CACBOHIDRAT.
Cacbohidrat l nhng hp cht hu c tp chc v thng c CTC : Cn(H2O)m
Cacbohidrat chia lm 3 nhm ch yu :
+Monosaccarit l nhm khng b thy phn . vd: glucoz , fuctoz
+isaccarit l nhm m khi thy phn mi phn t sinh ra 2 phn t monosaccarit .vd : saccaroz , mantoz
+Polisaccarit l nhm m khi thy phn n cng mi phn t sinh ra nhiu phn t monosaccarit . vd : tinh bt ,
xenluloz .
7.1.1 GLUCOZ
I.L tnh .Trong mu ngi c nng glucoz khng i khong 0,1% .
II.Cu to .Glucoz c CTPT : C6H12O6
Glucoz c CTCT : CH2OH-CHOH-CHOH-CHOH-CHOH-CH=O hoc CH2OH[CHOH]4CHO .
Glucoz l hp cht tp chc
22
2Ag
+ Bng Cu(OH)2 mi trng kim: natri gluconat v Cu2O gch (nhn bit glucoz)
+ Tc dng vi dung dch nc Brom(Br2)
C5H11O5CHO + Br2 + H2O
C5H11O5COOH + 2HBr
Fructoz
OH
glucoz
23
( - glucoz)
C6H12O6
( fructoz )
c, Phn ng vi sa:
C12H22O11+ (CaOH)2 + H2O
C12H22O11CaO.2H2O + CO2
- glucoz)
Trong phn t cn c nhm OH hemiaxetal nn c th m vng to nhm chc CHO nn c phn ng trng bc v
lm mt mu nc brom
C12H22O11
AgNO3 / NH 3
2 Ag
a) Phn ng vi Cu(OH)2
24
( - glucoz)
C6H12O6
( glucoz )
7.1.4.TINH BT XENLULOZ
I. TINH BT
1. Tnh cht vt l:L cht rn, dng bt v nh hnh, mu trng, khng tan trong nc lnh, tan trong nc nng (
600C)
2. Cu trc phn t:
Tinh bt thuc loi polisaccarit, Phn t tinh bt gm nhiu mt xch -glucoz lin kt vi nhau.
CTPT : (C6H10O5)n .
Cc mt xch -glucoz lin kt vi nhau to hai dng:
-Dnh l xo: bng lin kt -1,4 - glucozit khng phn nhnh (amiloz) .
-Dng l xo bng lin kt -1,4 glucozit v -1,6 glucozit phn nhnh (amilopectin).
Tinh bt ( trong cc ht ng cc , cc loi c )
3. Tnh cht ha hc.
a) Phn ng thy phn: tinh bt b thy phn thnh glucoz.
(C6H10O5)n + nH2O n C6H12O6
b) Phn ng mu vi iot:To thnh hp cht c mu xanh tm (phn ng dng nhn bit Tinh bt)
II. XENLULOZ
1. Tnh cht vt l, trng thi t nhin.
-Xenluloz l cht rn dng si, mu trng, khng tan trong nc v dung mi hu c, nhng tan trong nc
Svayde (dd thu c khi ha tan Cu(OH)2 trong amoniac) .
2. Cu trc phn t:
- Xenluloz l mt polisaccarit, phn t gm nhiu gc -glucoz lin kt vi nhau bng lin kt -1,4 glucozit
-CT : (C6H10O5)n hay [C6H7O2(OH)3]n
25