Bi s 1.

1. Th no l s lai ho sp3, sp2, sp?

2. Lin kt xichma(), lin kt pi() l g?
Trn c s s lai ho cc obitan nguyn t hy m t s hnh thnh cc lin kt trong
phn t CH4, C2H4, C2H2.
Bi gii.
1.
a. Lai ho sp3:
- Xt cho nguyn t cacbon.
2 2
2
Cu hnh electron:
6C 1s 2s 2p .
Lp electron ngoi cng:

Trng thi kch thch

Trng thi c bn

Mt obitan 2s t hp vi ba obitan 3p to ra bn obitan mi(4 obitan lai ho sp3) hon

ton ng nht v c dng khc vi cc obitan ban u. Bn obitan lai ho sp3 c cc trc to
vi nhau mt gc 109028' v hng v bn nh ca mt hnh t din u. S lai ho ny
c gi l lai ho sp 3 hay lai ho t din.
z

10

9 02

8'

2pz

2s

y
2py
sp3

2px

b. Lai ho sp2:
Mt obitan 2s t hp vi hai obitan 2p cho ba obitan lai ho sp2 hon ton ng nht.
Ba obitan lai ho sp2 ny c trc to vi nhau mt gc 1200 v hng v ba nh ca mt tam
gic u. S lai ho ny gi l lai ha sp2 hay lai ho tam gic.

1200

2p

2p
2s

sp2

Mi nguyn t C cn mt obitan 2p c trc thng gc vi mt phng cha 3 obitan lai

ho sp2.

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c. Lai ho sp:
Mt obitan 2s t hp vi mt obitan 2p cho hai obitan lai ho sp hon ton ng nht.
Hai obitan lai ho sp ny c trc nm trn mt ng thng nhng hng v hai pha khc
nhau. S lai ho ny gi l lai ho sp hay lai ho ng thng.

2p

sp

2s

Mi nguyn t C cn hai obitan 2p c trc thng gc vi nhau v thng gc vi trc

ca hai obitan lai ho sp.
2.a. Lin kt xichma():
- Lin kt c hnh thnh do s xen ph ca cc obitan dc theo trc ni hai ht nhn
nguyn t(xen ph trc).

s-s

v.v...

b. Lin kt pi():
- Lin kt c hnh thnh do s xen ph bn ca hai obitan p c trc song song vi nhau.
Vng xen ph nm hai pha ca ng thng ni hai ht nhn.

CH4
- Nguyn t C trng thi lai ho sp3.
- Bn obitan lai ho sp 3 ca C xen ph vi 4 obitan s ca nguyn t H to thnh 4 lin kt .

H
H

H
H

Phn t c dng t din u.

C2H4
- Hai nguyn t C u trng thi lai ho sp2.
- Mi nguyn t C s dng mt obitan sp2 xen ph vi nhau v hai obitan sp 2 cn li xen
ph vi obitan 1s ca hai nguyn t H to nn cc lin kt . Cc nguyn t C v H nm
trong cng mt mt phng.
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H
C

Hai nguyn t C cn hai obitan 2p khng tham gia lai ho c trc song song vi nhau
v thng gc vi mt phng cha cc nguyn t C v H. Hai obitan ny xen ph bn vi nhau
to thnh lin kt .

C2H2
- Hai nguyn t C trng thi lai ho sp.
- Mi nguyn t C s dng mt obitan lai ho sp xen ph vi nhau v obitan sp cn li xen
ph vi obitan 1s ca nguyn t H hnh thnh nn cc lin kt . Cc nguyn t C v H nm
trn mt ng thng.

Mi nguyn t C cn li hai obitan 2p khng tham gia lai ho, chng xen ph bn
tng i mt to ra hai lin kt .

------------------------------------------------------------------------------------------------------Ghi ch
- Obitan lai ho c kh nng xen ph cao hn so vi obitan cha lai ho.
- Lin kt tng i bn do vng xen ph gia hai obitan tng i ln.
Lin kt t bn do vng xen ph gia hai obitan khng ln.
- Lin kt n: gm 1 lin kt .
Lin kt i: gm 1 lin kt v 1 lin kt .
Lin kt ba: gm 1 lin kt v 2 lin kt .
- Tng t nguyn t C, khi tham gia lin kt nguyn t N cng c th cc trng thi lai ho
sp3(R1 R2 R3N), sp2(RCH = NOH), sp(HC N), v.v...
- Do s xen ph trc ca cc obitan khi to lin kt n(lin kt ) nn c s quay t do xung
quanh trc ni hai ht nhn nguyn t to lin kt m vn bo ton lin kt.
Lin kt i, lin kt ba vi s xen ph bn ca cc obitan to lin kt nn lm trit
tiu s quay t do xung quanh trc ni hai ht nhn nguyn t to lin kt.
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Bi s 2.
1. Cho bit kiu lai ho v loi lin kt(, ) ca cc nguyn t trong cc hp cht sau:
ClCH2 - CHO; CH2 = CH - CN; CH2 = C = O
2. Cho bit kiu lai ho ca cc nguyn t C, N, S, Br trong cc hp cht sau:
CH3 - CH3; CH2 = CH2; CH CH; C6 H6; CH2 = C = CH2; NH2OH; H2S; BF4-; HO - C
N.
Bi gii.
1.

Cl
p

CH2
sp3

CH2

CH
sp2

CH2

sp2

sp2

O
sp2

C
sp

C
sp

CH
sp2

N
sp

O
sp2

2.
CH3 - CH3 :

C sp 3 C sp 3

CH2 = CH2 :

C sp 2 C sp 2

CH CH

C sp C sp

C sp2

C6H6 :

CH2 = C = CH2 :
NH2OH:

C sp 2 C sp C sp 2

N sp 3

H2S : Sp
BF4- :

Bsp 3

HO - C N : Csp - Nsp.

Bi s 3.
1. So snh di lin kt:

a.

*
b'
a'
b*
CH3 a CH2
CH3 CH3
CH
CH2
*

CH3

c*

c'

Gia (a , b , c ); (a', b', c').

b. CH

CH

CH

CH2

CH

CH

CH2

CH

CH

CH2

Gia (m, n, l).

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2. So snh gc lin kt, di lin kt C - C, C - H, phn cc ca lin kt CH gia cc

cht sau:
C2H2; C2H4; C2H6
Bi gii.
1. a. Do s lai ho cc obitan ca nguyn t cacbon m ta c bn knh ca cacbon lai ho:

C sp3 > C sp 2 > C sp .

rC

C th:

sp 3

= 0,771A 0 ; rCsp 2 = 0,665 A 0 ; rC

= 0,602 A0
sp

a* > b* > c* v a' > b' > c' ( bi lin kt cng tng th di lin kt cng gim).
C th: C sp 3 C sp 3 = 1,54 A ; C sp 2 C sp 2 = 1,30 A ; C sp C sp = 1,20 A
0

b. Tng t phn a ta c: n > l > m.

c. - Gc lin kt: V cc nguyn t cacbon trng thi lai ho khc nhau th gc lin kt khc
nhau.
0

109 28'

120

C sp 2

C sp 3

180

C sp

Gc lin kt trong C2H6(C lai ho sp 3)< C2H4(C lai ho sp2) < C2H2(C lai ho sp).
- di lin kt C - C: bi lin kt cng tng th di lin kt cng gim.
C2H2 < C2H4 < C2H6.
- di lin kt C - H: Do s lai ho ca nguyn t cacbon nn:
di lin kt C - H: C2H2 < C2H4 < C2H6.
- phn cc ca lin kt CH: Do cc trng thi lai ho khc nhau th nguyn t cacbon
c m in khc nhau.

C th:

sp 3

sp 3

< C

sp 2

< Csp

= 2,5 ; Csp 2 = 2,8 ; Csp = 3,3

phn cc ca lin kt CH: C2H6 < C2H4 < C2H2.

c. Xiclohexan - 1(S),3(S) - iol.

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Bi s 4.
Khi cho 2 - brombutan v 2 - metyl - 3 - trimetylamonipentan tc dng vi dung dch
KOH/C2H5 OH thu c nhng sn phm no?
Bi gii.
1.

CH3 CH2 CH CH3

KOH/C2H5OH

CH3 CH CH CH3 + CH3 CH2 CH2 CH2

Sn phm chnh
Br
Sn phm ph
------------------------------------------------------------------------------------------------------Ghi ch
Qui tc Zaixep. Trong phn ng tch nucleofin, nhm X(Br, H2O+, ...) tch ra cng vi
nguyn t cacbon bn cnh c bc tng i cao hn to ra olefin c tng i nhiu
nhm th hn hai nguyn t cacbon mang ni i.
Br
C

CH 3CH 2

- HBr

H
H
H

OH

Br
CH 3CH CH
H

CH2
H

OH

H
C

H 3C

OH

HO

I'

H
CH 3
II

Br

H
C

II'

CH 3CH2
H
CH 3
H 3C
Trng thi chuyn tip II n nh hn I bi c nhiu nhm ankyl hn. Sn phm II'
bn hn (nhit hiro ho 119,54kJ/mol) sn phm I'(nhit hiro ho 126,94kJ/mol).
Lp th phn ng tch.
Qui tc Ingol: S tch lng phn t ch xy ra d dng khi m 4 trung tm phn ng
nm trong mt mt phng v cc nhm th c tch ra dng trans(v tr anti) i vi nhau.
KOH/C2H5OH
CH3 CH2 *CH CH3
CH3 CH CH CH3
- HBr
Dng cis hay trans
Br
Xt mt i quang v nhn dc theo trc C2 - C3:
H
Br
CH3 CH3
H
CH3
C
Br H
C
CH3
H
CH3
CH3
H
H
H
H
Cu dng bn
OH
trans - 2 - buten

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CH3

Br
CH3

CH3

C
C

CH3

Br CH3

H
CH3

H
H

OH

cis - 2 - buten
Cu dng km bn
------------------------------------------------------------------------------------------------------CH3
2.
CH 3 CH CH
CH 3
CH3
CH
1
2
3
4
OH
Sn phm Hopman(chnh)
CH 3 CH CH CH2 CH 3
CH3
- N(CH3)3, HOH
H 3C N CH 3
CH 3 C
CH 2 CH 3
CH
Sn phm Zaixep(ph)
CH 3
Qui tc Zaixep khng p dng c vi X c th tch ln, ht electron.
Gii thch.
- Mun xt s to thnh sn phm Zaixep ta nhn dc theo trc C2 - C3:
C2

C3

OH

H
H

H 3C
H 3C

CH 2CH 3

CH 3
CH3

C
CH2CH3

CH3
Sn phm Zaixep(ph)

CH3
Cu trc ny rt khng bn.

- Nhn dc theo trc C3 - C4:

C4

C3

OH
H
H

CH 3
CH
CH 3

H 3C
H 3C

H
CH 3

CH3

C
CH(CH3)2

H
Sn phm Hopman(chnh)

CH 3
Cu trc ny bn hn.

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Bi s 5.
t chy hon ton mt hirocacbon A ri hp th ht sn phm chy vo mt bnh
ng dung dch Ca(OH)2. Sau th nghim thy khi lng bnh tng 26,24 gam. Lc thu c
20 gam kt ta. un si nc lc mt thi gian lu li thu c 10 gam kt ta na.
Khi cho mt lng A bng ng lng t chy trn vi clo 3000C thu c
hn hp C gm 4 sn phm dn xut cha clo ca A l ng phn ca nhau vi hiu sut
100%. Hn hp C c t khi hi so vi H2 nh hn 93.
Xc nh cng thc ca A v tnh thnh phn % theo khi lng mi cht trong hn
hp C.
Bi gii.
Ghi ch
Trong phn ng th halogen ca ankan, thc nghim cho thy, nu coi kh nng phn
ng ca CI - H l 1 th kh nng phn ng ca CII - H v CIII - H nh sau:
CI - H
CII - H
CIII - H
1
3,9
5,1
Clo ho 27 C
0
1
4,3
7,0
Clo ho 100 C
1
3,3
4,4
Clo ho 300 0C
0
1
82
1600
Brom ho 127 C
------------------------------------------------------------------------------------------------------0

t
A + O2
CO2 + H2O
Khi dn sn phm chy vo dung dch Ca(OH)2 th hi nc ngng t cn CO2 c
phn ng:
CO2 + Ca(OH)2 CaCO3 + H2O
(1)
c th c:
2CO2 + Ca(OH)2 Ca(HCO3)2
(2)
0

mbnh tng =

mCO2 + m H 2 O

un nng nc lc li thu c kt ta chng t c (2), v:

t0
Ca(HCO3)2
CaCO3 + CO2 + H2O
1),( 2 ), ( 3 )
(

nCO2 = nCaCO 3 (1) + 2nCaCO 3 (3 ) =

n H 2O =

26,24 0,4.44
= 0,48mol
18

(3)

20
10
+ 2x
= 0,4mol
100
100

nCO2 < n H 2O A l ankan CnH2n + 2.

CnH2n + 2

3n + 1
t0
O2
nCO2 + (n + 1)H2O
2

n
0, 4
=
n = 5. A : C5H12.
n + 1 0,48
Ta c:

C5H12

nCl2 C5H12 - nCln +

nHCl

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M C 72 + 34,5n
=
< 9,3 n = 1, 2, 3.
2
2

dC / H2 =

C5H12

CH3 - CH2 - CH2 - CH2 - CH3

CH3

CH2

CH

CH3

CH3

> 11

> 10

>6

>6

S dn xut clo

CH3
CH3

CH3

CH3
A l:

CH3

CH

CH2

CH3 (n = 1)

CH3

CH3

CH

CH2

CH3

CH2

CH

Cl

CH3

CH3

CCl

Cl2, 3000C

CH2

CH3

CH2

CH3

CH3

1:1

CH3

CH3

CH3

CH

CH

CH3

Cl

CH

CH2

CH3

CH2Cl

CH3
I

Kh nng phn ng vi clo ca H - C : H - C : H - C III = 1 : 3,3 : 4,4

% CH2

CH

Cl

CH3

Tng t:

%CH3

CCl

6.1

CH2

CH3 =

CH2

CH3 = 22%

II

. 100% = 30%

6.1 + 2.3,3 + 1.4,4

CH3
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CH

% CH3

CH

%CH3

CH3 Cl
CH CH2

CH3 = 33%
CH2Cl = 15%

CH3
l % mi cht v s mol cng l % v khi lng ca mi cht do chng c khi
lng phn t bng nhau.

Bi s 6.
Khi cho isobutilen vo dung dch H2SO4 60%, un nng ti 800C thu c hn hp
gi tt l i - isobutilen gm hai cht ng phn ca nhau A v B. Hiro ho hn hp ny
c hp cht C quen gi l isooctan. C l cht c dng nh gi nhin liu lng.
C cng c th c iu ch bng phn ng trc tip ca isobutilen vi isobutan khi
c mt axit v c lm xc tc.
Hy gi tn C theo IUPAC v vit cc phng trnh phn ng gii thch s to thnh
A, B, C.

Bi gii.
H2SO4 H+ +

HSO4-

+
C CH2 + H

CH3

CH3

CH3

CH3

CH3 + CH3

CH2

C
CH3

CH3

CH2

C
CH3

CH3

CH2

Zaixep

CH

CH3 (2)

CH3

CH3
CH3
CH3

CH3
CH3

(1)

CH3

CH3
CH3

CH3

CH3

CH3

CH3
CH3
CH3 (A) (> 80%)

-H
CH3

C
CH3

H sinh ra li quay v (1). Qu trnh xy ra lin tc.

CH2

CH2

CH3
(B) (< 20%)

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CH3

CH3
CH3

CH

CH3

H2/Ni

CH3

CH3

CH CH3
CH3

CH3

CH3

(A)

CH2

Isooctan(C)
2,2,4 - trimetylpentan
(Qui c c ch s octan l 100)

Isobutilen vi isobutan khi c mt axit v c lm xc tc cng to ra C: C ch ca

qu trnh tng t trn nhng ch khc qu trnh:
CH3
CH3

CH3

CH2

CH3 + CH3

CH3

CH3

CH

CH3

C
CH3

CH3

CH3
H3C

CH3

CH2

CH CH3
CH3

(C)

+ CH3
CH3 sinh ra li lp li (2). C nh vy.

CH3
C
CH3

Bi s 7.
Hon thnh phn ng theo dy bin ho sau:

dd Na2CO3

A'

A
Cl2 B
CCl4

Propilen
Cl2
CCl4

NaOH c Hn hp hai cht

cha 2 nguyn t Cl

Zn, t0

B'

(CH3)3COK Hn hp cht (CH3)3COK Hn hp

cha 1 nguyn
hai hirocacbon
C
t Cl

AgNO3/NH3

B'
Bi gii.
500 C
400

CH2 = CH - CH3

+ Cl2

CH2 = CH - CH2Cl + HCl

(A)
CH2 = CH - CH2Cl + Na2CO3 + H2O CH2 = CH-CH2OH + NaHCO3 + NaCl
(A')

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CH2

CH

CH2 + Cl2

CCl4

Cl

CH2

CH

CH2

Cl

Cl

Cl (B)

CH2
CH2 CH

CH2 + NaOHc

Cl

Cl

Cl

CH2

Cl

Cl

Cl

CH2

CH

Cl

CH3

CH3

CH2
CH3

CH2

CH + Zn
Cl

CH

CH2 + Cl2

CH

CH2

Cl

Cl

C
C

Cl
CH2 + NaCl + H2O

(CH3)3COK
- (CH3)3COH
- KCl

CH2

CH

CH3

CH

CH3
CH3

ZnCl2

C CH2 +
(B')

CH3

CH2 AgNO /NH

3
3
CH

CH + NaCl + H2O

Cl
Cl
C CH2 +
(B')

CH2

CH2 + Zn

CH2 C

CH

CH

CH2

Cl

Cl

ZnCl2

CH2
Cl (CH3)3COK CH2
CH
- (CH3)3COH
CH3
Cl - KCl
CH2

Cl
C CAg + CH2

CH2

CH

CH2

Bi s 8.
Su hirocacbon A, B, C, D, E, F u c cng thc phn t C4H8. Cho tng cht vo
brom trong CCl4 khi khng chiu sng th thy A, B, C, D tc dng rt nhanh., E tc dng
chm hn, cn F th hu nh khng phn ng. Cc sn phm thu c t B v C l nhng
ng phn quang hc khng i quang(ng phn lp th i - a) ca nhau. Khi cho tc dng
vi H2(Pd, t0) th A, B, C u cho cng mt sn phm G. B c nhit si cao hn C.
1. Xc nh cng thc ca 6 hirocacbon trn. Gii thch?
2. So snh nhit si ca E v F.
3. Nu c C, D, E, F. Hy nu phng php ho hc nhh bit chng.

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Bi gii.

1. Cc ng phn c th c ca C4H8:

CH3

CH2

CH2

CH

CH3

CH3

CH

CH3

CH3

CH3
CH

H2C

CH2

H2C

CH2

CH2

CH

CH
CH3

CH2
H2C

CH

CH3

- V F hu nh khng phn ng vi Br2/CCl4, nn F l:

H2C

CH2

H2C

CH2

- E tc dng chm vi Br2/CCl4, nn E l:

CH2

H2C

CH

CH3

- V A, B, C c hiro ho u cho cng mt sn phm G chng t A, B, C c khung C nh

nhau, nn cn li D:

CH3

CH2

C
CH3

- V B, C tc dng vi Br2/CCl4 cho nhng ng phn quang hc khng i quang ca

nhau(c t nht 2 *C), nn B v C l ng phn cis - trans ca nhau.
Do B c nhit si cao hn C nn B l ng phn cis(phn cc hn).

B: CH3

CH3
C

C:

CH3
C

C
H

C
CH3

A: CH3 - CH2 - CH = CH2

C ch(cng hp trans):

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H
C

Br2

CH 3

H3 C

H3C

Br

(1) H

H3C

Br
CH 3

H3C Br

Br

Br

Br
H

(2)

CH 3
Br

CH 3

CH 3

Br
CH 3

CH 3

CH 3

CH 3
H

Br

Br

Br

C
(C)

C
CH3

CH 3
II

(Threo)

I
H

CH 3

Br

CH 3

(1)

(2)

Br

H3C

H
C

H
CH 3

Br

CH 3

CH 3

Br

CH 3

Br

Br

Br

CH3
Br2

Br

Br

CH3
III
Erythro(meso)

(I, III); (II, III) l nhng cp ng phn quang hc khng i quang.

2. ME = MF v d dng thy (E) > 0; (F) = 0 nn E c nhit si cao hn F.

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3. Nhn bit C, D, E, F.
- Dng dung dch Br2 nhn ra F v khng phn ng.
- Cn li D, E, F cho tc dng vi dung dch KMnO4 long, ngui. E khng phn ng nn
nhn ra.
- C, D em hp nc(H+) ri cho hai ru tng ng tc dng vi (HClc + ZnCl2).
Cht no vn c ngay l ru bc 3 sn phm ca D.
Cht no vn c kh chm l sn phm ca C(ru bc 2).
Cc phng trnh phn ng:

CH3
CH

CH2

CH3
CH
(C)

Br
Br2

CH3

CH

Br2

BrCH2

CH3

CH3

CH3
CH2
CH3 +

CH

Br2

CH2

CH2

Br
3CH3

CH3

Br Br

CH3

H2C

CH

CH

CH

CH

CH3

Br
3CH3

CH3 + 2KMnO4 + 4H2O

CH

CH

OH

OH

CH3

+ 2 MnO2 + 2KOH
CH3
3CH2

3CH2

CH3 + 2KMnO4 + 4H2O

OH

CH3
CH2

H2C
CH3
CH3

CH
CH
C
CH3

CH
CH2

+ HOH

H+

CH3 + 2 MnO2 + 2KOH

OH

khng phn ng

CH3 + KMnO4
CH3 + HOH

H+

CH3

CH2

CH3
CH3

CH

CH3

OH
OH

CH3

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CH3

CH3
CH3

OH + HCl

ZnCl2

CH3
CH3

CH2 CH

CH3 + HCl

CH3
ZnCl2

Cl

+ H2O(nhanh)

CH3
CH3

CH2 CH
Cl

OH
CH3

CH

CH2

OH

OH

CH3 + H2O(chm)

H+

CH3

CH

CH2

OH2 OH

- H 2O

CH3

CH

CH2
OH

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