CacChuyenDe HoaHuuCo QuanHanThanh NguyenDinhDo

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1

c Son V Tng Hp Theo:
Sch Gio Khoa 11 Nng Cao
Cc Chuyn Ha Hc Hu C (Nguyn nh )
Cu Hi Gio Khoa Ha Hu C (Quan Hn Thnh)

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Mc Lc
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

3

7.0 Mt s dng ton v phng php gii trong ha hu c: ............................................... .....23
7.1 Phn ng oxi ha kh trong ha hu c: .................................................................... .....23
7.1.1 Tnh s oxi ha ca mt nguyn t cacbon (hay Nit) trong phn t hu c: ..........23
7.1.2 Cn bng phn ng oxi ha kh trong ha hu c ..................................................23
7.2 Bin lun tm CTPT t cng thc nguyn (cng thc n gin nht) ....................... .....25
7.2.1 Phng php tch ring nhm chc: .........................................................................25
7.2.2 Phng php dng s lin kt . ..............................................................................25
7.3 Bin lun tm CTPT t cc d kin phn ng. ............................................................. .....26
7.4 ng dng nh lut bo ton khi lng gii nhanh mt s bi ton ha hc hu c.
.......................................................................................................................................... .....27
7.5 Cc phn ng xy ra kh cho CO
2
( hoc SO
2
) tc dng vi dung dch baz. ........... .....29
7.5.1 Cc phn ng xy ra khi cho CO
2
(hoc SO
2
) tc dng vi mt dd NaOH. ........ .....29
2
tc dng vi Ca(OH)
2
hoc Ba(OH)
2
. ........ .....30
7.5.3 Ton v s tng, gim khi lng dung dch: ...................................................... .....31
7.5.4 Vit s phn ng, iu ch............................................................................... ......33

BI TP ............................................................................................................................ ......34

4
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).

+Kiu xen ph bn: s xen ph thc hin hai bn
trc ni gia hai ht nhn nguyn t. Lin kt cng
ha tr hnh thnh bng cch xen ph bn l lin kt
.

+Th tch xen ph cng ln, lin kt cng bn. Xen
ph bn hn lin kt .

2. Gc Hidrocacbon- Nhm th- Nhm chc.
2.1 Gc Hidrocacbon: L phn cn li ca phn t hidrocacbon sau khi mt i mt hay nhiu nguyn
t hydro. Nu mt 1 H ta c gc ha tr I, mt 2 H ta c gc ha tr II, thng thng k hiu l R.
V d: Gc no, ha tr I nh: Metyl:(CH
3
-); etyl:(C
2
H
5
-)cn gi l gc ankyl ( cng thc tng qut
C
n
H
2n+1
- ).
2.2 Nhm th: L nhm nguyn t quyt nh cc tnh cht ha hc c trng ca mt loi hp cht.
V d: Nhm chc cc ru l (-OH), ca axit l (-COOH).
2.3 Cacbocation: L ion ca hidrocacbon, c mt in tch dng nguyn t cacbon ( tuy c th tn ti
c lp nhng rt km bn).
V d: Cation metyl CH
3
- ( Nguyn t cacbon thiu 1 electron nn mang mt in tch dng).
2.4 ng ng: Hin tng cc HCHC c cu to v tnh cht tng t nhau, nhng thnh phn phn t
hn km nhau mt hay nhiu nhm (-CH
2
) gi l cc cht ng ng vi nhau, chugn1 hp thnh mt
dy ng ng.
2.5 ng phn: Hin tng cc cht c cng mt cng thc phn t nhng c cu to khc nhau nn c
tnh cht khc nhau c gi l ng phn ca nhau.
5
*Cc loi ng phn chnh:
-ng phn dng mch cacbon ( do thay i dng mch h khng h, c nhnh v dng mch vng):
V d:

-ng phn v tr ( do thay i v tr nhm th, nhm chc, ni i hay ni ba):
V d: CH
2
=CH-CH
2
-CH
3
v CH
3
-CH=CH-CH
3

(but-1-en) (but-2-en)
-ng phn nhm chc ( do cc cht hu c c nhm chc khc nhau).
V d: CH
3
-CH
2
-OH v CH
3
-O-CH
3
( Ru etylic) (Dimetyl ete)
-ng phn hnh hc ( hay lp th: Cis Trans):
*Nguyn nhn: Do s xp xp trong khng gian khc nhau ca nguyn t hay nhm nguyn t gn vi
cacbon mang ni i.
*iu kin c ng phn hnh hc:
-iu kin cn: HCHC phi c cha ni i.
-iu kin : Cc nhm th gn cng mt cacbon mang ni i phi khc nhau.

* Cch xc nh ng phn cis v trans:
-Bc 1: mi C
mang ni i, chn mt
nhm th ln.
-Bc 2: Nu hai nhm
th ln cng pha ->
dng cis.
Nu hai nhm
th ln khc pha ->
dng trans.
V d:

6

*Cch vit ng phn ng vi cng thc phn t:
-Bc 1: Xc nh bt bo ha () v nhm chc c th c.
bt bo ha (): cho bit s lin kt (ni i, ni ba) hoc dng mch vng, hoc c hai m
HCHC c th c.
Cch tnh gi tr (): Vi HCHC dng C
x
H
y
O
z
N
t
X
u
(X l halogen) ta c:
2 2 ( )
2
x y u t + +
=

Bng gi tr v loi HCHC tng ng ( c th c )

C
x
H
y
C
x
H
y
O C
x
H
y
O
z
C
x
H
y
N
t
0 Ankan
Ru no, n
chc, Ete no, n
chc
Ru no, 2 chc
este + ru
Amin no
1 Anken xicloanken
Andehit, xeton,
ru, ete cha no
Axit. Este,
Andehit+Ru,
andehit+este
Amin khng no
2
Ankin, ankadien,
xicloanken
Andehit, xeton c
cha ( C=C)
Axit, este cha no,
andehit 2 chc

4
Benzen dn xut
ca halogen
Amin thm
5
Benzen c 1 lin
kt (C=C) ngoi
vng.

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 C
x
H
y
O
z
N
t
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 .

7

3. Mt s gc hidrocacbon v gi tn cn ch :

Gc
Cu to Gi tn
CH
3
CH
2
CH
2
- n-propyl
CH
3
-CH-
|
CH
3
Iso-propyl (iso: nhm CH
3
gn
vo v tr C th 2 t ngoi mch
m vo)
CH
3
CH
2
CH-
|
CH
3

Sec-butyl (Sec: -CH
3
gn vo v
tr C th 3 t ngoi mch m
vo )
CH
3

|
CH
3
C
|
CH
3

Tert- Butyl
No
CH
3

|
CH
3
C CH
2

|
CH
3

Neo-pentyl
CH
2
=CH- Vinyl
CH
3
-CH=CH- Propenyl
Khng no
CH
2
=C
|
CH
3
Iso- propenyl
C
6
H
5
- Phenyl
C
6
H
5
CH
2
Benzyl
Thm
CH
3
C
6
H
4
p-Tolyl

8

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:
3 2 5
3 2 2 5 2
C H OH Cl CH

C
CH OH H OH COOH
CH NH H NH

2
3 3 3 2
H Cl
Cl CH
NH
CH NH CH CH COOH COOH

Nu nhm th X y electron, ta ni X gy ra hiu ng cm dng (+I). Nu nhm th X ht
electron, ta ni X gy ra hiu ng cm m. ( -I).
V d: Nu ta ly lin kt n ( -C-H) lm chun. Nu nguyn t hay nhm nguyn t ht e mnh
hn H th s gy hiu ng cm m. Nu nguyn t hay nhm nguyn t y e mnh hn H th s gy
hiu ng cm dng.
Sau y l nhm th X gy ra hiu ng cm thng gp:
(-I): -NO
2
> -F > -Cl > -Br> -I > -OH
(+i): -C(CH
3
)
3
> -CH(CH
3
)
2
> -C
2
H
5
> -CH
3
> -H

4.2 ng dng
Hiu ng cm dng gii thch v so snh tnh axit hay tnh baz ca cc cht hu c hoc dng
gii thch c ch ca phn ng.
V d: So snh tnh linh ng ca nguyn t H trong nhm (-OH) ca Phenol v ru?
Trong khi nhm Phenyl ht e th gc ankyl trong phn t ru y e v pha nguyn t O. Do vy
mt d e trn nguyn t O tng ln, s phn cc ca lin kt trong nhm (-OH) gim i, tnh linh ng
ca nguyn t H gim theo:
R O H , C
6
H
5
O H

Hoc theo sch gio khoa Ha Hc11 nng cao trang 231 c gii thch nh sau ( theo chng trnh
phn ban- Khoa hc t nhin).
V sao phenol c lc axit mnh hn ancol? V sao phn ng th vo nhn thm phenol d hn
benzen? l do nh hng qua li gia gc phenyl v nhm hydroxyl nh
sau:

Cp electron cha tham gia lin kt ca nguyn t oxi do cch cc
electron ca vng benzen ch mt lin kt nn tham gia lin hp vi cc
electron ca vng benzen lm cho mt electron dch chuyn vo vng
benzen. iu dn n h qu sau:
9
+Lin kt O-H tr nn phn cc hn, lm cho nguyn t H linh ng hn.
+Mt electron vng benzen tng ln, nht l v tr ortho v para( v tr ortho-v tr cacbon th 6
v 2,para-cacbon th 4, meta -cacbon th 3 v 5 .. xem SGK Ha hc 11 nng cao trang 187), lm cho
phn ng th d dng hn so vi benzen v ng ng ca n.
+Lin kt C-O tr nn bn vng hn so vi ancol, v th nhm OH phenol khng b th bi gc axit
nh nhm OH ancol
4.2.1 Dng hiu ng cm so snh mnh yu ca cc axit hu c:
Trong phn t axit hu c
O
R C O H
, do s c mt ca nhm cacbonyl ||
O
C
nn lin kt O- H
vn 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
C
2
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 :

C
||
O
H O H

3 2 5

|| ||
O O
CH C O H C H C O H

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:
3 2
Cl CH Cl CH
|| || ||
O
CH C O H C O H C O H
O 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:
3 2 2 3 3
H CH
(I) (II) (III)
CH NH NH NH CH

Kt qu l mt in tch m trn nguyn t N ca (III) > (I)>(II).
4.2.3 D on sn phm phn ng- kh nng phn ng.
Da vo s ht hoc y electron ca nhm th X, ta c th d on c sn phm phn ng, hoc
kh nng phn ng ca mt cht.
V d:D on sn phm phn ng ( sn phm chnh ) ca phn ng: CH
3
CH =CH
2
+HCl .
10
Do CH
3
l nhm y electron nn trong phn t propen xy ra s phn cc: .
Kt qu l phn cation ca tc nhn tn cng vo nhm CH
2
, cn phn anion ca tc nhn kt hp
vo nhm CH nh sau:
CH
3
CH =CH
2
+ HCl CH
3
CHCl CH
3

V d 2: D on kh nng phn ng ca benzen v toluen vi Br
2
( bt st xc tc).
Trong phn t toluen, do CH
3
l nhm y electron lm tng mt electron trong vng thm
khin phn ng th Brom xy ra d hn so vi benzen.

5. Cc loi phn ng chnh trong ha hu c.
5.1 Phn ng th
L phn ng trong mt hoc mt nhm nguyn t phn t hu c b thay th bi mt hoc mt
nhm nguyn t khc .

Tn Ankan Aren Ankin
CH
4
+Cl
2
CH
3
Cl +HCl

C ch gc t do
+ Br
2
+HBr
C ch ion

HC CH + 2 AgNO
3
+3 NH
3

Ag C C Ag
+2NH
4
NO
3
+NH
3
Th ion kim loi

Cc loi phn ng th thng gp:
Halogen ha, nitro ha.Ankyl ha ankan, aren.
Th H ca axit, andehit, xeton, este ha, thy phn, trng ngng.

5.2 Phn ng cng.
L phn ng trong phn t tc nhn tch thnh 2 phn, gn vo phn t phn ng, phn ng xy ra
ch yu lin kt . bt bo ha phn t gim ( nh ngha theo SGK11 Nng cao trang 130: Phn
t hu c kt hp thm vi cc nguyn t hoc phn t khc ).
HC CH + 2H
2
H
3
C -CH
3

Cc phn ng cng thng gp:
Cng H
2
(kh H
2
), cng H
2
O (hyrat ha), cng halogen, cng halogenua hiro, trng hp

*Quy tc cng Mc- cp-nhi cp.(SGK 11 nng cao trang 162)
Khi cng mt tc nhn bt i xng ( cng axit hoc nc HA, H
2
O) vo lin kt C=C ca anken
bt i xng, H ( phn mang in tch dng) u tin cng vo C mang nhiu H hn (cacbon bc thp
hn), cn A (phn mang in tch m) u tin cng vo C mang t H hn ( cacbon bc cao hn).

11
CH
2
=CH CH
3
+ HCl
2 3
2 3
| |
H Cl
( Chnh)
| |
Cl H
(Sp Phu.)
CH CH CH
sp
CH CH CH

;
2 3
3
|
CH
CH C CH HOH = +
2 3
3
2 3
3
H OH
| |
|
CH
( chnh)
H
| |
|
CH
(sp phu. )
CH C CH
Sp
OH
CH C CH

5.3 Phn ng tch.
L phn ng trong mt vi nguyn t hoc nhm nguyn t b tch ra khi phn t.
2 2
| |
H OH
H C CH
H
2
C=CH
2
+ H
2
O
Cc phn ng tch thng gp:
hiro (tch H
2
); hyrat ( tch H
2
O);
Crackinh ankan; tch ihalogen; tch halogennua hiro.
5.4 Phn ng oxi ha:
L phn ng trong tc nhn cung cp oxi, phn t cht phn ng c s tng s oxi ha.
+Oxi ha hon ton: phn ng chy ca HCHC vi oxi.
+Oxi ha khng hon ton (oxi ha chm): tc nhn oxi ha thng l KMnO
4
, CrO
3
, K
2
Cr
2
O
7
, O
2
,
c xc tc bng Cu, Pt, NO,
************So snh v phn bit mt s phn ng thng gp trong hu c*************
Cng Trng hp
-L phn ng 1 ln gia 2 phn t to thnh mt
phn t mi

-Cht phn ng phi khng no ( hoc c cha lin
kt ).
V d: CH
2
=CH
2
+HBrCH
3
CH
2
Br
-L qu trnh cng hp lin tip nhiu phn t nh
ging nhau hay tng t nhau to thnh phn t
ln hay cao phn t.
-Cht phn ng v tc nhn phi u khng no.

V d: nCH
2
=CH
2
(-CH
2
CH
2
-)
n

Trng hp Trng ngng
-Qu trnh cng hp lin tip nhiu phn t
nh (monome) to thnh phn t ln(polime)
c gi l phn ng trng hp.

-c im cu to cc monome tham gia phn
ng trng hp l phi c lin kt kp.
V d:CH
2
=CH
2
;
C
6
H
5
CH=CH
2
;
CH
2
=CH Cl ;
CH
2
=CH CH=CH
2
;

nCH
2
=CH
2
(-CH
2
CH
2
-)
n

-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 H
2
O, NH
3
,
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: H
2
N CH
2
COOH ;
H
2
N (CH
2
)
6
NH
2
;
HOOC (CH
2
)
4
COOH ;
H
2
N (CH
2
)
5
COOH ;
nH
2
N CH
2
COOH
2 2
( ) + nH
||
O
n
HN CH C O

12

Hyrat ha Thy phn
-Cht phn ng c lin kt cn tc nhn l H
2
O.

-Phn ng xy ra 1 chiu.
V d:
CH
2
=CH
2
+H
2
O CH
3
CH
2
OH
-Cht phn ng l este, ete, dn xut halogen ca
C
x
H
Y
, cn tc nhn l nc.
-Phn ng thun nghch.
V d:
CH
3
Cl+H
2
O CH
3
OH + HCl

X phng ha Thy phn
-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 +H
2
O ROH+RCOONa +H
2
O
-Cht phn ng l este, ete, dn xut halogen ca
C
x
H
Y
, cn tc nhn l nc.

-Phn ng thun nghch.
V d:
CH
3
Cl+H
2
O CH
3
OH + HCl

6. Hp cht hu c c nhm chc.
6.1 Phn loi HCHC c nhm chc.
-Thnh phn: Gc hyrocacbon + nhm chc.
-Cng thc tng qut: C
x
H
y-k
A
k
(iu kin k y).
n chc a chc Tp chc
1 nhm chc ( k=1) 2 nhm chc cng loi tr ln (k 2) 2 nhm chc khc loi tr ln
(k 2)
Gc C
x
H
y
no (C
n
H
2n+2-k
A
k
) HCHC no.
Gc C
x
H
y
khng no (C
n
H
y-k
A
k
) HCHC khng no.

6.2 Bng cng thc tng qut mt s HCHC quan trng.
Hp cht hu c Cng thc tng qut iu kin
Hp cht cha C, H, O
Hp cht cha C, H, O, N
Hp cht cha C, H, O, X
(X l halogen)
C
x
H
y
O
z

C
x
H
y
O
z
N
t

C
x
H
y
O
z
X
u

y 2x +2
y 2x +2 +t
y 2x +2 u
Ru , no
Ru n chc
Ru bc I, n chc

Ru n chc, no, bc I
R(OH)
x
hay C
n
H
2n+2-x
(OH)
x
C
x
H
y
OH
C
x
H
y
CH
2
OH
C
n
H
2n+1
(OH) hay C
n
H
2n+2
O
C
n
H
2n+1
CH
2
OH

x,n 1
x 1, y 2x+1
x 0, y 2x+1
n 1
n 0
Andehit
Andehit no
Andehit n chc
Andehit on chc, no
R(CHO)
x

C
n
H
2n+2-x
(CHO)
x

R CHO hay C
x
H
y
CHO
C
n
H
2n+1
CHO hay C
m
H
2m
O
x 1
x 1, n 0
x 0, y 2x+1
n 0, m 1
13
Axit n chc
i axit no
Axit n chc, no
R COOH hay C
x
H
y
COOH
C
n
H
2n
(COOH)
2

C
n
H
2n+1
COOH hay C
m
H
2m
O
2

x 0, y 2x+1
n 0
n 0, m 1
Este n chc
Este n chc, no
R COO R
C
n
H
2n
O
2

R H
n 2
Amin n chc
Amin n ch, no
Amin bc I, no, n chc
C
n
H
y
N
C
n
H
2n+3
N
C
n
H
2n+1
NH
2

y 2x+3
n 1
n 1
iu kin chung: x, y, z, t, u, n, m u N
(R ) l gc hidrocacbon no hay khng no

6.3 Bng cc dy ng ng thng gp ng vi CTTQ ( cng thc tng qut ).
CTTQ C th thuc dy cc ng ng iu kin
C
n
H
2n
O
+ Andehit no, n chc ( ankanal)
+ Xeton no, n chc.
+Ru n chc, khng no (c mt ni i
phn gc hidrocacbon)
n 1
n 3
n 3

n 3
C
n
H
2n
O
2

+Axit hu c no, n chc.
+Este no, n chc.
n1
n 2
C
n
H
2n+2
O
+Ru no, n chc (ankanol)
+Ete no, n chc
n 1
n 2

6.4 Ha tnh ca mt s cht hu c cn ch :
6.4.1 Ru:
*Ru l hp cht c nhm OH lin kt vi gc hyrocacbon. Bc ca ru bng bc ca C mang
nhm OH
*Nu thay th H on mch nhnh ca hirocacbon thm bng nhm ( -OH) ta c ru thm.
Cn phn bit ru thm vi cht thuc loi phenol:
V d: ( Ru benzylic)
( p-Crezol)
Ru thm c phn ng th trn gc (C
6
H
5
-):

14

*Tc dng vi natri :
+Ancol tc dng vi kim loa kim to ra ancolat v gii phng kh hiro.
2
( ) ( )
2
x y z x y z
z
C H OH zNa C H ONa H + +
CH
3
CH
2
OH +Na C
2
H
5
ONa +
2
1
2
H
+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.
2 2
2 2 2 2
CH HO
| |
2 ( ) 2
|
OH CH
CH CH CH Cu OH CH O Cu O CH H O

+ +
2 2
| | | |
OH OH OH CH HO OH CH

ng (II) glixerat, mu xanh lam
Phn ng ny dng nhn bit glixerol v cc poliancol m cc nhm OH nh vi nhng nguyn
t C cnh nhau, chng hn nh etylen glicol.
*Tch nc to ete:

*Tch nc to lin kt .
Khi un nng vi H
2
SO
4
c 170
0
C, c mi phn t ancol tch 1 phn t nc to thnh 1 phn t
Anken.

Hoc ankadien nu cht phn ng co 1 lin kt :

CH
3
OH khng c phn ng tch nc to anken
Hng ca phn ng tch nc tun theo quy tc zai-xp:

Quy tc zai-xp (Zaitsev):
Nhm OH u tin tch ra cng vi H nguyn t C bc cao hn bn cnh to thnh lin kt i
C=C.
15
V d:

*Este ha:
Axit + Ru Este +H
2
O

*Oxi ha:
+Ru bc (I) b oxi ha cho andehit.
RCH
2
OH +CuO RCHO +Cu +H
2
O
+Ru bc (II) b oxi ha cho xeton.
'
|
OH
R CH R
+CuO
2
'
||
O
R C R Cu H O + +

*Cch chuyn ru bc (I) sang bc (II):
R CH
2
CH
2
OH R CH =CH
2
+H
2
O

R CH =CH
2
+H
2
O
3
|
OH
R CH CH

6.4.2 Phenol.
-Phenol l nhng hp cht hu c m phn t c cha nhm hiroxyl (-OH) lin kt tc tip vi
nguyn t cacbon ca vng benzen.
*Tnh axit.
Phenol c lc axit mnh hn ancol ( khng nhng tc dng c vi kim loi kim m cn phn ng
c vi NaOH), tuy nhin n vn ch l mt axit rt yu (b axit cacbonic y khi phenolat). Dung
dch phenol khng lm i mu qu tm.
+Tc dng vi Na

Phenolat natri
+Tc dng vi NaOH.

* Phn ng th vng thm.
Phn ng th vng thm phenol d hn benzen ( iu kin m du hn, th c ng thi c 3
nguyn t H cc v tr ortho v para)
+Tc dng vi dung dch Brom.
16

+Tc dng vi HNO
3
c:

*Tc dng vi CH
2
O:

Ch : Tnh linh ng Ca H trong OH tng dn nh sau:

ROH < H
2
O < < H
2
CO
3
< ||
O
R C OH

Nn: + Na
2
CO
3
Khng phn ng
Ngc li:
+H
2
O +CO
2
+NaHCO
3

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); CH
3
CH=O( axetandehit)
*Phn ng cng H
2
( phn ng kh):
Khi c xc tc Ni un nng, andehit cng vi hiro to ra ancol bc I:
RCHO +H
2
RCH
2
OH
CH
3
CH=O + H
2
CH
3
CH
2
OH
17
*Phn ng cng nc, cng hiro xianua:
-Lin kt i C=C fomandehit c phn ng cng nc nhung sn phm c hai nhm OH cng
nh vo 1 C nn khng bn, khng tch ra khi dung dch c:
2
OH
|
|
OH
HCH O HOH H C = +
-Hiro xianua (H C N)cng vo nhm cacbonyl xy ra hai giai on, anion NC

phn ng giai
on u, ion H
+
phn ng giai on sau:
3 3
3 3
CH CH O
|
C N
| |
C
N C CH CH O
CH CH O H CH CH OH

+
= +
+
N C N

*Phn ng brom v kali pemanganat:
Andehit rt d b oxi ha, n lm mt mu nc Brom, dung dch kali pemanganat v b oxi ha
thnh axit cacboxylic.
RCH=O +Br
2
+H
2
O RCOOH + 2HBr

* Tham gia phn ng trng gng (Phn ng trng bc).
RCHO +2 AgNO
3
+3NH
3
+H
2
O RCOONH
4
+2NH
4
NO
3
+2Ag.
V d:OHC CHO + 4 AgNO
3
+6NH
3
+2H
2
O NH
4
OOCCOONH
4
+4NH
4
NO
3
+4Ag
Ch : HCHO khi tc dng vi dung dch AgNO
3
/NH
3
s to t l mol l 1:4 trong khi cc andehit
n chc khc ch to bc theo t l mol 1:2
HCHO + 4 AgNO
3
+6NH
3
+2H
2
O (NH
4
)
2
CO
3
+4NH
4
NO
3
+4Ag

*Phn ng vi Cu(OH)2 trong mi trng kim:
RCHO+2Cu(OH)
2
+NaOH RCOONa+Cu
2
O +3H
2
O
V d: CH
3
CHO + 2 Cu(OH)
2
+NaOH CH
3
COONa+Cu
2
O +3H
2
O

*Phn ng trng ngng vi phenol:

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: H
3
C CO CH
3

18
*Xeton cng tham gia phn ng cng hiro khi c mt Ni xc tc, un nng to thnh ancol bc (II):
3 3 2
||
O
CH C CH H +
3 3
|
OH
CH CH CH

*Phn ng cng nc, cng hiro xianua:
3 3 3 3
C N
|
||
CH C CH H CN CH C CH
+
|
O OH
(xianohidrin)

*Phn ng gc hirocacbon
Nguyn t hiro bn cnh nhm cacbonyl d tham gia phn ng.
V d:

6.4.5 Axit (axit cacboxylic)
-Axit cacboxylic l nhng hp cht hu c m phn t c nhm cacboxyl ( -COOH) lin kt trc
tip vi nguyn t cacbon hoc nguyn t hiro.
* Tnh axit:
Axit cacboxylic in li khng hon ton trong nc theo cn bng:
R COOH +H
2
O H
3
O
+
+ R COO
-
;
3
[ ][ ]
[ ]
a
H O RCOO
K
RCOOH
+
=
(K
a
l mc o lc axit, K
a
cng ln th axit cng mnh v ngc li)
Axit cacboxylic l mt axit yu. Tuy vy, chng c tnh cht ca 1 axit: lm qu tm ha , tc
dng c vi kim loi gii phng hiro, vi oxit kim loi, vi baz, vi mui v ru.
HCOOH +Na HCOONa +1/2 H
2

2CH
3
COOH +MgO (CH
3
COO)
2
Mg +H
2
O
2CH
2
=CH COOH +Na
2
CO
3
2CH
2
CH COONa +CO
2
+H
2
O
HOOC COOH +Ca(OH)
2

2
2
\ /
Ca
OOC COO H O +

-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 )

*Phn ng tch nc lin phn t:
Khi cho tc dng vi P
2
O
5
. hai phn t axit tch i mt phn t nc to thnh phn t anhirit axit:
19

*Phn ng th gc no.
Khi dng photpho xc tc, Cl ch th cho H cacbon bn cnh nhm cacboxyl
CH
3
CH
2
CH
2
COOH +Cl
2

3 2
|
Cl
CH CH CHCOOH HCl +

*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.

*Phn ng cng vo gc khng no.
Axit khng no tham gia phn ng cng H
2
, Br
2
, Cl
2
nh hirocacbon khng no.

*Mt s phn ng c bit.
+HCOOH cn cho phn ng trng gng:
HCOOH + 2AgNO
3
+4NH
3
+H
2
O (NH
4
)
2
CO
3
+2NH
4
NO
3
+2Ag
+Axit cha no cn cho phn ng cng, trng hp.
CH
2
=CH COOH +H
2
O HO CH
2
CH
2
COOH
nCH
2
=CH COOH ( )
2
|
COOH
n
CH CH
6.5 Cc phng php chnh iu ch mt s cht hu c quan trng:
6.5.1 iu ch ru:
* Ln men tinh bt:
(C
6
H
10
O
5
)
n
+nH
2
O nC
6
H
12
O
6

C
6
H
12
O
6
2C
2
H
5
OH + 2CO
2

*Hirat ha anken xc tc axit
C
n
H
2n
+H
2
O C
n
H
2n+1
OH
CH
2
=CH
2
+ H
2
O CH
3
CH
2
OH

* T andehit v xeton.
R CHO +H
2
R CH
2
OH ( ru bc I )
Ni

H
2
SO
4
, 300
0
C
H
+
enzim
enzim
xt, t
0
, P
P
20
R CO R R CHOH R ( Ru bc II)

*Thy phn dn xut halogen trong mi trng kim:
R Cl +NaOH R OH +NaCl
C
2
H
5
Cl + NaOH C
2
H
5
OH +NaCl

2 2 2 2
3 3
| | | | | |
Cl Cl OH OH OH
CH CH CH NaOH CH CH CH NaCl
Cl
+ +

*Thy phn este ( x phng ha):
R COO R + NaOH R COONa + ROH

*Metanol c th sn xut t 2 cch sau:
+CH
4
+H
2
O CO + 3H
2

CO +2H
2
CH
3
OH
+ 2CH
4
+O
2
2CH
3
OH

6.5.2 Phenol:
*T C
6
H
6
:
C
6
H
6
C
6
H
5
CH(CH
3
)
2
C
6
H
5
OH + CH
3
COCH
3

C
6
H
6
+Cl
2
C
6
H
5
Cl +HCl
C
6
H
5
Cl + NaOH C
6
H
5
OH +NaCl
*T natri phenolat:
C
6
H
5
ONa +HCl C
6
H
5
OH + NaCl
C
6
H
5
ONa + CO
2
+H
2
O C
6
H
5
OH + NaHCO
3

* Oxi ha iso propyl benzen:

6.5.3 Andehit:
*Oxi ha ru bc (I):
R CH
2
OH +CuO R CHO +Cu +H
2
O

CH
3
OH +CuO HCHO +Cu +H
2
O
t
o
,
t
o
,
t
o
, p
Fe
1)O
2
(kk); 2)H
2
SO
4
CH
2
=CHCH
3
, H
+

t
o
,xt,p
t
o
,xt,p
t
o
,xt
t
o

t
o

t
o

Ni,t
o

21

Fomandehit cn c iu ch bng cch oxi ha metanol nh oxi khng kh 600-700
0
C vi xc
tc l Cu hoc Ag.
2CH
3
OH + O
2
2HCHO + 2H
2
O
*Oxy ho ankan iu kin thch hp.
CH
4
+ O
2

HCHO + H
2
O
*Thy phn dn xut 1,1 ihalogen.
3
Cl
|
2
|
Cl
CH CH NaOH + CH
3
CHO +2NaCl +H
2
O

*Oxi ha cumen ri ch ha vi axit sunfuric thu c axeton vi phenol:
(CH
3
)
2
CH C
6
H
5
tiu phn trung gian CH
3
CO CH
3
+C
6
H
5
OH

*2CH CH +O
2
2CH
3
CH=O
*C
2
H
2
+H
2
O CH
3
CHO

*RCOOH=CH
2
+NaOH RCOONa + CH
3
CHO

6.5.4 Xeton:
*Oxi ha ru bc (II):
'
|
OH
R CH R +CuO
2
'
||
O
R C R Cu H O + +
*T Canxi axetat
(CH
3
COO)
2
Ca CH
3
CO CH
3
+CaCO
3

Hoc t CH
3
COONa:
2CH
3
COONa CH
3
CO CH
3
+Na
2
CO
3

6.5.5 Axit cacboxylic.
*Oxi ha hirocacbon, ancol
C
6
H
5
CH
3
C
6
H
5
COOK C
6
H
5
COOH
+Oxi ha ru bc I tng ng:
5CH
2
CH
2
OH + 4KMnO
4
+ 6H
2
SO
4
5CH
3
COOH + 2K
2
SO
4
+4MnSO
4
+11H
2
O
+Oxi ha hirocacbon cha no:
5CH
3
CH = CH CH
3
+8KMnO
4
+12H
2
SO
4
10CH
3
COOH + 4K
2
SO
4
+8MnSO
4
+12H
2
O
+Oxi ha ankan thch hp:
H
3
O
+
KMnO
4
, H
2
O,t
0

t
o
,
t
o
,
2)H
2
SO
4
, 20% 1)O
2

HgSO
4
,t
o
PdCl
2
, CuCl
2
t
o
,
t
o
,xt
22
R CH
3
RCOOH +H
2
O

*T dn xut halogen:
R X R C N R COOH
+Thy phn dn xut 1,1,1 trihalogen.
3
Cl
|
3
|
Cl
CH C Cl NaOH + CH
3
COOH +3NaCl + H
2
O

*Ln men gim:
CH
3
CH
2
OH +O
2
CH
3
COOH +H
2
O

*Oxi ha andehit tng ng:
CH
3
CH=O + O
2
CH
3
COOH
OHC CHO + O
2
HOOC COOH

*T metanol
CH
2
OH +CO CH
3
COOH
*T mui natri ca axit cacboxylic:
R COONa +H
2
SO
4()
R COOH +NaHSO
4

t
0

[O], xt. t
0

t
o
, xt
t
o
, xt
t
o
, xt
Men gim, 20-30
0
c
H
3
O
+
,t
0
KCN
23

7. Mt s dng ton v phng php gii trong ha hu c:
7.1. Phn ng oxi ha kh trong ha hu c:
7.1.1 Tnh s oxi ha ca mt nguyn t cacbon (hay Nit) trong phn t hu c:
Mt phn ng oxi ha kh trong ha hu c thng xy ra s bin i s oxi ha ca cacbon ( hay
nit), do ta cn nm cch tnh s oxi ha ca chng.
-Vit CTCT dng khai trin ca cht hu c.
-Tnh in tch xut hin trn nguyn t C (hay N); cn tnh s oxi ha ( vi gi thit cc i electron
chung b lch hon ton v pha nguyn t c m in ln hn). y cng chnh l s oxi ha cn
tnh.
Cn ch rng m in O> N> C> H.

V d: Tnh s oxi ha ca cc nguyn t C v N trong cc hp cht:
a) CH
2
=CH CH
2

b) CH
3
CH
2
CH
2

c) CH
3
NO
2

d) CH
3

Gii
2 1 3
) H b) H H H

= C H
a H
C C H C

3 1 3

H H H H H H
) H O
C N
c

3 3 3 1
d) H

H

H
H C N C C H
+ +

O H O

7.1.2 Cn bng phn ng oxi ha kh trong ha hu c
-Tnh s oxi ha ca cc nguyn t trong phn ng. tm ra cc nguyn t (thng l hai v thng c
cacbon) c s thay i s oxi ha.
-Vit cc bn phn ng th hin qu trnh oxi ha kh.
-Tm h s thch hp khi nhn cc bn phn ng cho mi h s ri cng li th s electron trit
tiu.
-t cc h s tm c trn vo phng trnh cho ri kim tra s nguyn t ca mi nguyn t
hai v cho bng nhau.
V d: Cn bng phn ng oxi ha kh sau theo phng php thng bng electron:
a)CH
2
=CH
2
+KMnO
4
+H
2
O CH
2
OH CH
2
OH +MnO
2
+KOH
b)CH
3
CH
2
OH +KMnO
4
+H
2
SO
4
CH
3
COOH + K
2
SO
4
+H
2
SO
4

c)CH
3
CH
2
OH +K
2
Cr
2
O
7
+H
2
SO
4
CH
3
CHO + K
2
SO
4
+Cr
2
(SO
4
)
3
+H
2
O
d)C
6
H
5
NO
2
+Fe +HCl C
6
H
5
NH
2
+FeCl
2
+H
2
O
e) C
6
H
5
CH
3
+KMnO
4
C
6
H
5
CH
3
COOK +MnO
2
+KOH +H
2
O

24
Gii
2 2 7 1 4
2 2 4 2 2 2 2
2 1
7
)
| |
OH OH
2 2 2
3
a
C H C H K MnO H O C H CH MnO KOH
C e C
Mn e Mn
+ +

+
= + + + +
=
+ =
3
4
2
2 2 4 2 2 2 2
1 7 3 2
3 2 4 2 4 3 4 2 4 2
1 3
X 5
7 2
4
1 7 3 2
3 2 4 2 4 3 4 2 4 2

3 2 4 3 2 2
)
4

5
5 4 6 5 4 2 11
X
X
X
CH CH KMnO H O CH OH CH OH MnO KOH
b
CH C H OH K MnO H SO CH COOH Mn SO K SO H O
C e C
Mn e Mn
CH C H OH K MnO H SO CH COOH Mn SO K SO H O
+
+ + +
+
+ +
+ + +
= + + + +
+ + + + +
=
+ =
+ + + + +
( )
( )
1 6 1 3
3 2 2 6 7 2 4 3 2 4 2 4 2
3
1 1
3
6 3
1
1 6 1 3
3 2 2 6 7 2 4 3 2 4 2 4 2
3
3 0 3 2
6 5 2 6 5 2 2 2
)
CH H OH K O H SO CH HO K SO SO H O
2

2 6 2
3CH H OH K O 4H SO 3CH HO K SO SO 7H O
.
X
X
c
C Cr C Cr
C e C
Cr e Cr
C Cr C Cr
d
C H N O Fe HCl C H N H FeCl H
+ +

+ +
+ +
+ +
+ + + + +
=
+ =
+ + + + +
+ + + +
3 3
1
0 2
3
3 0 3 2
6 5 2 6 5 2 2 2
3 7 3 4
6 5 3 4 6 5 3 2 2
3 3
1
7 4
2
3 7 3 4
6 5 3 4 6 5 3 2
6

2
3 6 3 2
.
C H H K O C H H COOK O KOH H O
6

3
C H H 2K O C H H COOK 2 O
X
X
X
X
O
N e N
Fe e Fe
C H N O Fe HCl C H N H FeCl H O
e
C Mn C Mn
C e C
Mn e Mn
C Mn C Mn
+
+
+ +
+ + +
+
+ +
+ + +
+ =
=
+ + + +
+ + + +
=
+ =
+ +
2
KOH H O + +

25

7.2.Bin lun tm CTPT t cng thc nguyn (cng thc n gin nht)
7.2.1 Phng php tch ring nhm chc:
-Theo phng php ny, ta tch cng thc cht hu c cho thnh cng thc c nhm chc(ha tr I
) ri dng cng thc:
S H +s nhm chc 2s C+2
(Du = xy ra khi cht hu c cho l no, mch h)
V d: Cng thc nguyn ca mt andehit no, mch h l (C
2
H
3
O)
n
. Tm CTPT andehit trn:
Gii
Cng thc andehit trn c th vit C
2n
H
3n
O
n
hay C
n
H
2n
(CHO)
n

Ta phi c : 2n+n=2n+2 n =2
Vy CTPT andehit trn l C
4
H
6
O
2

V d 2: t chy hon ton 14.6g axit cacboxylic A thu c 26.4g CO
2
v 9gH
2
O. Tm CTPT axit.
Gii
3
26, 4. 7, 2
11
9
1
9
14, 6 (7, 2 1) 6, 4
C
H
O
m
m
m
= =
= =
= + =

Gi cng thc A l C
x
H
y
O
z
, ta c:
7, 2 1 6, 4
: : : :
12 1 16
=0, 6 :1: 0, 4
=3:5:2
x y x =

Vy A c cng thc nguyn ( cng thc n gin nht) l (C
3
H
5
O
2
)
n

Cng thc A cp1 th vit C
3n
H
5n
O
2n
hay C
2n
H
4n
(COOH)
n

Ta phi c: 4n + n 2.2n +2 => n 2
Nhng n=1 cho cng thc C
3
H
5
O
2
khng tn ti.
Vy n=2, tc A c CTPT l C
6
H
10
O
4

7.2.2 Phng php dng s lin kt .
Ta bit rng hp cht C
x
H
y
O
z
Q
t
c s lin kt ti a l:
2 2 ( )
2
x y t + +

Theo phng php ny, ta tnh xem cht hu c cho c cha bao nhiu lin kt ( hoc ti thiu
bao nhiu lin kt ), ri dng cng thc tnh s lin kt trn tm n.
V d:Mt axit cacboxylic mch h A c cng thc nguyn (C
3
H
4
O
3
)
n
. Tm CTPT ca A.
Gii
Cng thc A c th vit C
3n
H
4n
O
3n

A c cha
3
2
n
nhm COOH (or 2O to nn 1 nhm COOH => nO s to n.O/2 )
26
Do mi nhm COOH c 1 lin kt , ngoi ra A mch h, no nn phn t A c
3
2
n
lin kt .
Vy
3 2.3 2 4
2 2
3 2 2 2
n n n
n n n
+
=
= + =

Do A c CTPT l C
6
H
8
O
6
.

V d 2:
Mt hp cht A c cng thc (C
4
H
9
ClO)
n

a) Tm cng thc phn t ca A.
b) Xc nh cng thc phn t ca A, bit un A vi dung dch NaOH thu c 1 xeton.
Gii
a)S lin kt trong phn t A 0 nn:
2.4 2 (9 )
0
2
2 2 0 1
n n n
n n
+ +

+

A c CTPT l C
4
H
9
ClO
b)A pha c CTPT l
3 2 3
|
Cl
CH COH CH CH

7.3. Bin lun tm CTPT t cc d kin phn ng.
Vi dng ny ta cn nm vng tnh cht ha hc cc hp cht hu c:
-Cc lin kt trong vng benzen ca Hirocacbon thm cho c phn ng cng H
2
nhng khng
lm mt mu dung dch Brom. Chng han 1 mol stiren C
6
H
5
CH =CH
2
c th cng hp 4 mol H
2
nhng
ch lm mt mu 1 mol Br
2
trong dung dch Brom.
-Ch c cc hp cht axit, pehnol, este v axit cho phn ng vi dung dch NaOH.
-Cc hp cht cho phn ng trng gng gm c andehit, axitfomic, este fomiat v cc mui fomiat.
-S x phng ha este phi to mui v ru; nu khng thy ru trong sn phm phn ng th l
do ru to ra khng bn, chuyn thnh andehit, xeton hoc axit (sau axit bin thnh mui).
Cn bit nhng ru khng bn gm:
+Ru c nhm OH gn C mang ni i. Trng hp ny, ru s chuyn thnh andehit hoc
xeton.
V d:
. nh
2 3
C th
CH CH OH CH CHO =

(khng bn) (bn)
. nh
2 3 3 3
| ||
OH O
C th
CH C CH CH C CH =

(khng bn) (bn)
+Ru c hai hoc ba nhm OH gn cng 1 C. Trng hp ny, ru s tch nc tr thnh
andehitm xeton hoc axit
V d:
27
2
2
3 3
3 3 3
|
OH
OH
|
CH
| ||
OH O

H O
H O
CH CH OH CH CHO
C OH CH C CH

2
3 3
OH
|
CH
|
OH
H O
C OH CH COOH

V d:
A l hp cht c cng thc C
8
H
8
. 3,12g A phn ugn71 va vi 2,688 lt H
2
(ktc) hoc vi 4,8g
Br
2
trong dung dch Brom. Xc nh CTCT ca A.
Gii
S mol
2
2
3,12
0, 03
104
2, 688
0,12
22, 4
4, 8
0, 03
160
H
Br
A
n
n
= =
= =
= =

V
2
: 1: 4
A H
n n =

nn A c 4 lin kt phn ng c vi H
2
.
V n
A
: n Br
2
= 1:1 nn A c 1 lin kt phn ng dc vi H
2.

=>A c 3 lin kt khng phn ng c vi dung dch Brom, 3 lin kt ny phi nm trong vng
benzen
=>A c vng benzen l 1 lin kt ngoi vng
=>A c CTCT l C
6
H
5
CH=CH
2

7.4. ng dng nh lut bo ton khi lng gii nhanh mt s bi ton ha hc hu c.
C nhng bi ton hu c nu gii theo cch thng thng s xut hin nhng kh khn nh:
+C qu nhiu kh nng phn ng, khin phi chia thnh nhng trng hp gii, lm bi ton tr
nn di dng ( v d phn ng crackinh butan c th to C
4
H
8
v H
2
; CH
4
v C
3
H
6
; C
2
H
6
v C
2
H
4
. Hoc
dn hn hp C
2
H
2
v H
2
qua bt Ni thu c hn hp X c th gm C
2
H
6
v H
2
; C
2
H
6
, C
2
H
4
v H
2
; C
2
H
6

v C
2
H
4
).
+c mt h phng trnh ton hc c qu nhiu n s, khin vic bin lun tr nn phc tp, lm
bi ton tr nn rm r.
Nhng kh khn ny c th gii quyt nh bit ng dng nh lut bo ton khi lng.
28
Pht biu nh lut : Khi lng cc cht trc phn ng phi bng tng khi lng cc cht sau
phn ng.
i khi nh lut ny cn c pht biu di dng nguyn l bo ton nguyn t: Khi lng
nguyn t X trc phn ng phi bng khi lng nguyn t X sau phn ng.
u im ca vic ng dng nh lut bo ton khi lng l hu ht khng t n s mol cho cc
cht dng ban u
V d:
Tin hnh crackinh , gan n-butan c hn hp X. Dn X qua bnh nc Brom d thy khi lng
bnh tng 16,8g. Kh thot ra khi bnh em t chy hon ton c 23,4g H
2
O v 35,2 CO
2
. Tnh m v
vit cc phn ng xy ra.
Gii
Cc phn ng c th xy ra:
C
4
H
10
C
4
H
8
+H
2

C
4
H
10
C
2
H
4
+C
2
H
6

C
4
H
10
C
3
H
6
+CH
4

C
4
H
8
+ Br
2
C
4
H
8
Br
2

C
2
H
4
+Br
2
C
2
H
4
Br
2

C
3
H
6
+ Br
2
C
3
H
6
Br
2

Kh thot ra c th gm CH
4
; C
2
H
6
; H
2
v C
4
H
10
d.
Cc phn ng chy:
CH
4
+2O
2
CO
2
+ 2H
2
O
2H
2
+ O
2
2 H
2
O
2C
2
H
6
+ 7O
2
4CO
2
+ 6H
2
O
2 C
4
H
10
+ 13O
2
8CO
2
+10H
2
O

p dng nh lut bo ton khi lng ta c:
m = m
x
= m
cc anken
+m
cc kh thot ra

nhng theo nguyn l bo ton nguyn t th:
m
cc kh tha ra
= m
C
trong CO
2
+ m
H
trong H
2
O

3 23, 4
35.2
11 9
12, 2
= +
=

Vy m= 16,8+12,2=29 (g).

29
7.5. Cc phn ng xy ra kh cho CO
2
( hoc SO
2
) tc dng vi dung dch baz.
y l vn xy ra bn v c nhng li gp nhiu trong hu c, v hu ht cc sn phm chy thu
c khi t cht hu c u hp th vo dung dch baz xc nh khi lng kt ta, khi lng
tng hoc gim ca dung dch

2
(hoc SO
2
) tc dng vi mt dung dch NaOH.
Khi cho CO
2
(hoc SO
2
) tc dng vi dung dch NaOH u xy ra ba kh nng to mui. bit kh
nng no xy ra, ta tnh t l
2
NaOH
CO
n
k
n
= ( hoc
2
NaOH
SO
n
k
n
= ), nu:
*k 2: ch to mui Na
2
CO
3

*k 1: ch to mui NaHCO
3

*1< k< 2: to c mui NaHCO
3
v Na
2
CO
3
.
Lu : Nu NaOH dng d th hn nhin k > 2 do ch to mui Na
2
CO
3
.

C nhng bi ton khng th tnh k. Khi y c th da vo nhng d kin ph tm ra kh nng to
mui.
V d:
+Hp th CO
2
vo dung dch NaOH d =>ch to mui Na
2
CO
3
.
+Hp th CO
2
vo dung dch NaOH, sau thm BaCl
2
d vo thy kt ta. Thm tip Ba(OH)
2
d
vo, li thy xut hin thm kt ta =>C s to c Na
2
CO
3
v NaHCO
3

Trong trng hp khng c cc d kin ph trn, ta phi chia trng hp gii.

V d:
t chy hon ton 0,1 mol C
2
H
6
ri hp th ton b sn phm chy vo bnh cha 200ml dung dch
NaOH 2.5M. Tnh khi lng cc mui sinh ra.
Gii
2 6 2 2 2
7
2 3
2
C H O CO H O + +
0,1mol 0,2mol
N
NaOH
=0,2.2,5=0,5
2
0,5
2,5
0,2
NaOH
CO
n
k
n
= = =
=> ch to mui Na
2
CO
3

CO
2
+2NaOH Na
2
CO
3
+H
2
O
0,2mol 0,2mol
Vy m Na
2
CO
3
= 0,2.106=21,2 (g).

30
2
tc dng vi dung dch Ca(OH)
2
hoc Ba(OH)
2
.

Tng t nh khi CO
2
tc dng vi NaOH; khi cho CO
2
tc dng vi dung dch Ba(OH)
2
cng xy ra
ba kh nng to mui. bit kh nng no xy ra, ta tnh t l
2
2
( ) Ca OH
nCO
k
n
= , nu:
*k 1: ch to mui CaCO
3

*k 2: ch to mui Ca(HCO
3
)
2

*k < k < 2: to c mi CaCO
3
v Ca(HCO
3
)
2

Ch :
Khi nhng bi ton khng th tnh k, ta c th da vo nhng d kin ph tm ra kh nng to
mui.
V d:
+Hp th CO
2
vo nc vi d =>ch to mui CaCO
3
.
+Hp th CO
2
vo nc vi trong thy c kt ta, thm NaOH d vo, li thy c kt ta na =>C
s to c CaCO
3
v Ca(HCO
3
)
2
.
+Hp th CO
2
vo nc vi trong thy c kt ta, lc b kt ta ri un nng phn nc lc li thy
kt ta na =>c s to c CaCO
3
v Ca(HCO
3
)
2
.
Nu khng c cc d liu ph trn, ta phi chia trng hp gii.

V d:
t chy hon ton 0,1 mol C
2
H
5
OH ri hp th ton b sn phm chy vo bnh cha 75 ml dung
dch Ba(OH)
2
2M. Tnh khi lng mui to ra.
Gii
Ta c phn ng chy :
C
2
H
5
OH +3O
2
2CO
2
+ 3H
2
O
0.1mol 0.2mol

2
2
2
( )
( )
0.075.2 0.15( )
0.2
1.33
0.15
Ba OH
CO
Ba OH
n mol
n
k
n
= =
= = =

=>C s to c BaCO
3
v Ba(HCO
3
)
2

Gi s to a mol BaCO
3
v b mol Ba(HCO
3
)
2
, ta c cc phn ng:
CO
2
+ Ba(OH)
2
BaCO
3
+H
2
O
a a a

2CO
2
+ Ba(OH)
2
Ba(HCO
3
)
2

2b b b

31
3
3 2
( )
2 0, 2 0,1
0,15 0, 05
197.0,1 19, 7( )
259.0, 05 12.59( )
BaCO
Ba HCO
a b a
a b b
m g
m g
+ = =

+ = =

= =
= =

Ch : Trong trng hp to c BaCO
3
v Ba(HCO
3
)
2
, nht thit CO
2
v Ba(OH)
2
u phi phn
ng ht.

7.5.3 Ton v s tng, gim khi lng dung dch:

Khi hp th sn phm chy vo dung dch baz, nht thit phi xy ra s tng, gim khi lng dung
dch.
Thng gp nht l hp th sn phm chy bng dung dch Ca(OH)
2
hoc dung dch Ba(OH)
2
. Khi
:

Khi lng dung dch tng = m
hp th
-m
kt ta

Khi lng dung dch gim = m
kt ta
- m
hp th

V d:
t chy hon ton hn hp A gm 2 hirocacbon lin tip trong dy ng ng. Hp th ton b sn
phm chy vo 3 phit dung dch Ca(OH)
2
0,01M c kt ta v khi lng dung dch tng 2.46g.
Cho dung dch Ba(OH)
2
d vo li thy kt ta na. Tng khi lng kt ta ca hai ln l 6.94g.
a) Tm CTPT 2 hirocacbon.
b) Tnh khi lng mi hirocacbon dng.
Gii
a)Theo bi CO
2
tc dng vi dung dch Ca(OH)
2
to 2 mui(xem 7.5.2). Gi s to a mol
CaCO
3
v b mol Ca(HCO
3
)
2
, ta c cc phn ng:
CO
2
+ Ca(OH)
2
CaCO
3
+ H
2
O
a a a

2CO
2
+ Ca(OH)
2
Ca(HCO
3
)
2

2b b b

Ca(HCO
3
)
2
+ Ba(OH)
2
CaCO
3
+ BaCO
3
+2H
2
O
b b b
3.0, 01 0, 03 0, 01
100 100 197 6,94 0, 02
a b a
a b b b
+ = = =

+ + = =

Vy
2
CO
n = a +2b =0,05
Mc khc do khi lng dung dch tng 2,46g nn ta c:
32
2 2
2
2
2
( ) 100 2, 46
(44.0, 05 ) 100.0, 01 2, 46
1, 26
1, 26
0, 07
18
CO H O
H O
H O
H O
m m a
m
m
n
+ =
+ =
=
= =

Do A l 2 hirocacbon ng ng chy cho
2 2
H O CO
n n > nn A phi l 2 Ankan .
t cng thc trung bnh 2 ankan l
2 2 n n
C H
+

Gi x l s mol 2 ankan dng, ta c cc phn ng:
2 2 2 2 2
3 1
( 1)
2
x x x( 1)
0, 05 0, 02
( 1) 0, 07 2, 5
o
t
n n
n
C H O nCO n H O
n n
xn x
x n n
+
+ | |
+ + +
|
\
+
= =

+ = =

Do n =2,5 nn 2 ankan lin tip l C
2
H
6
v C
3
H
8
.
b)Gi b,c l s mol 2 ankan trn, ta c:
0, 02
0, 01
2 3
2, 5 0, 01
0, 02
b c
b
b c
c
+ =

+
= =

Vy:
2 2
3 8
30.0, 01 0, 3( )
44.0, 01 0, 44( )
C H
C H
m g
m g
= =
= =

33

7.5.4 Vit s phn ng, iu ch.
Ngoi vic phi nm vng tnh cht ha hc ca cc hp cht hu c vit s phn ng v iu
ch cc hp cht huc, hc sinh cn phi nm vng cc quy tc phn ng( chn sn phm phn ng
cho ng), hiu c tng loi ru khng bn chuyn ha thnh nhng hp cht g ( chn phn ng
ph hp vi s ), nm c cc phn ng iu ch cc loi hp cht hu c v hiu ng chuyn dch
electron trong phn t hu c.
Nhc li cc quy tc phn ng:
+Quy tc Maccopnhicop: Dng xc nh sn phm chnh trong phn ng cng ca mt
hirocacbon cha no bt i xng vi mt tc nhn bt i xng:
Khi cng mt tc nhn bt i xng ( cng axit hoc nc HA, H
2
O) vo lin kt C=C ca anken
bt i xng, H ( phn mang in tch dng) u tin cng vo C mang nhiu H hn (cacbon bc thp
hn), cn A (phn mang in tch m) u tin cng vo C mang t H hn ( cacbon bc cao hn).
V d:
CH
2
=CH CH
3
+ HCl
2 3
2 3
| |
H Cl
( Chnh)
| |
Cl H
(Sp Phu.)
CH CH CH
sp
CH CH CH

;
2 3
3
|
CH
CH C CH HOH = +
2 3
3
2 3
3
H OH
| |
|
CH
( chnh)
H
| |
|
CH
(sp phu. )
CH C CH
Sp
OH
CH C CH

+Quy tc zai-xp: Dng xc nh sn phm chnh trong phn ng tch H
2
O ca ru hoc tch
HX ca dn xut halogen:
Nhm OH u tin tch ra cng vi H nguyn t C bc cao hn bn cnh to thnh lin kt i
C=C.
V d:

+Quy tc th vo vng benzen:Dng xc nh hng th tip theo sau nhm th th nht:
Khi trong vng benzen c sn mt nhm th y electron nh OH ; -NH
2
; -CH
3
... th hng th
tip theo l vo v tr ortho v para. Khi trong vng benzen c sn mt nhm th rt electron nh
NO
2
; -CHO... th hng th tip theo l kh hn, v u tin v tr meta.

V d:

34
V d:
Hon thnh s sau:
0
1500
m lanh. nhanh 4
2
B D E F CHO

C
C HCl NaOH
l
HCl NaOH
CH A H
+ +
+ +

Bit E l mui natri
Gii
0
0
0
0
0
1500
4 2 2
m lanh. nhanh
2
2 3
3 2 3 2 2
3 4 2 3
4 2 2
600
3 2
2
2 ( ) 3
2
C
L
t
t
t
NO
C
CH C H
CH CH HCl CH CHCl
CH CHCl NaOH CH CHO NaCl
CH CHO Cu OH NaOH CH COONa Cu O H O
CH COONa NaOH CH Na CO
CH O HCHO H O
CH CH HCl CH CHCl
C
+ =
= + +
+ + + +
+ +
+ +
+
0
3 2 3 2
2 2
t
H CHCl NaOH CH CHO NaCl H O + + +

BI TP:
1) So snh tnh baz ca NH
3
(I) ; CH
3
NH
2
(II) v C
6
H
5
CH
2
NH
2
(III).
(p n: (II) > (I) > (III) ).
2) Cn bng cc phn ng oxi ha kh sau theo phng php thng bng electron:
a. CH
3
CH=CH
2
+KMnO
4
+H
2
SO
4
CH
3
COOH +CO
2
+ K
2
SO
4
+MnSO
4
+H
2
O
b. CH
3
CH=C(CH
3
) CH
3
+KMnO
4
+H
2
SO
4
CH
3
COOH +CH
3
COCH
3
+K
2
SO
4
+MnSO
4
+H
2
O
(p n: a 1:2:3:1:1:1:2:4
b 5:6:9:5:5:6:3:1 )
3) Tnh s oxi ha ca cc nguyn t C c nh du * trong cc hp cht sau:
*
3 2
*
3 2
*
*
2 2
)
)
)
)
a CH C H OH
b CH O C H CH
c H COOH
d NH C H COOH
=

(p n: a= -1 ; b = 0; c= +2; d= -1 )
4) Phn tch thnh phn nguyn t ca mt axit cacboxylic c %C=34,61; %H=3,84.Tm CTPT A
(p n C
3
H
4
O
4
)
5) Tin hnh Crackinh ( C
n
H
2n+2
crackinh C
a
H
2a+2
+C
b
H
2b
trong a+b = n) m gam hn hp X
gm propan v butan c hn hp Y. Dn Y qua bnh cha Brom d thy khi lng bnh tng
8,2 v c 3,8g hn hp Z thot ra khi bnh. Vit cc phn ng c th xy ra v tnh m.
35
(p n: khi crackinh c 5 phn ng xy ra ta thu c 3 anken v khi lng anken chnh l khi
lng bnh Brom tng. Theo L bo ton khi lng ta tnh c m= 12 g).
6) Mt hn hp A gm 0,12 mol C
2
H
2
v 0,18 mol H
2
. Cho A qua Ni nung nng, phn ng khng
hon ton v thu c hn hp B. Cho B qua bnh Brom d thu c hn hp kh thot ra X. t
chy hon ton X ri hp th ton b sn phm chy vo bnh cha dung dch Ca(OH)
2
d thu
c 12g kt ta v khi lng bnh tng 8,88g. Tnh tng khi lng bnh Brom.
(HQG TP.HCM 99)
(p n: B c th gm C
2
H
4
; C
2
H
6
v C
2
H
2
; H
2
(v phn ng khng hon ton).
m Brom tng = m
A
m
x
=1,64 g ).
7) t chy hon ton 5,2 mt hirocacbon A. Sn phm chy c hp th ht vo dung dch
Ba(OH)
2
th c 39,4g kt ta. Thm NaOH d vo phn nc lc li thy xut hin 19,7g kt ta
na.
a)Tm CTPT ca A. Bit 96 < M
A
<115
b)Xc nh CTCT ca A bit 1 mol A tc dng vi ti a 4 mol H
2
hoc ti a 1 mol Br
2
trong
dung dch Brom.
(p n: a: C
8
H
8
; b: A c 4 lin kt c kh nng tc dng vi H
2
nhng ch c 1 lin kt c
kh nng tc dng vi Brom. Nn 3 lin kt cn li ca A nm trong vng benzen. Vy A c
vng benzen v 1 lin kt ngoi vng, CTCT: C
6
H
5
CH=CH
2
).
8) Hon thnh s sau:

2 2 3 3
A B E

CH

C
C H CHO F CH COOH

B

(Gi : A: C
2
H
4

B: C
2
H
5
OH
C: CH
2
=CH Cl
E: CH
3
COONa
F:CH
3
COONH
4
)
9) Hon thnh s :
3 3
0
2 4
/
,
B C

F
AgNO NH
E
H SO t
D E
A
G
+
+

Bit A,G ln lt c cng thc C
2
H
4
Br
2
v C
6
H
10
O
4

(HQG TP.HCM 2000)
(Gi : A:CH
2
Br CH
2
Br G: CH
3
COO CH
2
CH
2
OOCCH
3

B: CH CH F: HOCH
C: CH
3
CHO D:CH
3
COONH
4

E: CH
3
COOH

CacChuyenDe HoaHuuCo QuanHanThanh NguyenDinhDo

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