Bi tp cu trc ni ha hc

(1) Cho bit cng thc phn t ng ca cc cht sau

(a) CCl4
(d) SiF4

(b) AlH3
(e) CH3NH2

(c) CH2Cl2
(f) PH3

(2) Cho bit s hydrogen lin kt vi tng carbon - cng thc nguyn - trng thi lai ha cc carbon
(a)

Molecular formula
1H
sp2

sp2

HOOC

sp

HO

OH
sp

sp2

NHCH3

1H
sp2

sp3 3H

sp3
2H

sp2
1H

2H
sp2

C10H13O3N

sp3 1H

(b)

sp2
1H

HO

sp
1H

(d)
(c)

HO
sp

sp

1H

sp2
1H

sp2
1H

sp2

C sp

CH3

H3CO
sp3
3H

sp2

sp 1H

Molecular formula

sp 1H
sp2

sp2

sp2

sp2 1H

sp2
sp2
1H

sp2
1H

sp

sp3

sp3 2H
3

sp3
1H
sp3
3H

COOH

sp2
1H

C9H11O

sp 1H

sp
3H

C10H14O3
2

sp2

sp2 2H

sp
2H

1H2
sp

sp2
2H

C18H21O2

sp2 2H

Molecular formula

1H
sp2

sp

sp2
1H
sp2
1H

Molecular formula
2

sp2
2H

(f)
(e)

sp2
2H

sp3 3H

sp2
1H

sp3 3H
1H sp

C8H9O2N

sp2

sp2
1H

Molecular formula
sp2 1H

sp

sp2
2H

sp2

sp2

3H3
sp

1H

sp2 1H

Molecular formula
sp2

sp2

1H

sp2

sp2
1H

sp2
2

sp
1H

sp3 1H
sp3
3H

sp3 3H

(3) Cho bit trng thi lai ha cacbon - v vn o tp chng - gc lin kt ca cc hp cht

(a)

(c)

(b)

(d)

C13H18O2

OH

(e)

(f)

(g)

(h)

(4) _ Carbocation c 6 electron ha tr v nguyn t cacbon lai ha sp 3 (trong c mt orbital trng ; ton phn t
tch in dng)
_ Carbanion c 8 electron ha tr v nguyn t cacbon lai ha sp 3 (trong c mt orbital cha cp e t do khng
lin kt ; ton phn t tch in m)
(5) a) Cng thc Lewis ca cyclopropane:
b) Phn t cyclopropane lai ha sp2 , c gc lin kt khong 120o > 109,28o (gi tr gc ca cc H
alkane mch thng lai ha sp3 thng thng
c) Do gc lin kt ln sc cng ni ti phn t ln. Cyclopropane d m vng tham H
gia cc phn ng cng nn c hot tnh cao

H
H
H

(6) a) Phn t
khng bn. Lin kt ba C C c di ngn hn lin kt n, lm cho cc lin kt C-C xung
quanh b ko cng hn so vi phn t cyclopentane. Sc cng ni ti ca phn t qu ln nn phn t khng bn.
CH3

b) _ Cng thc

CH3
H
CH3

khng ng do tng quan ni xa-gn b sai lch (phi o ngc li mi ng)

CH3

_ Cng thc H
khng ng do khng c ni phi cnh no c nm gia hai ni nm cng trn mt
mt phng (iu ny s dn n lin kt b che khut ch khng quan st c)
(7) Cc cng thc cng hng:

CH2

CH CH CH CH2

H2C

CH CH

H3C

CH CH CH

H2C

H2C

CH CH CH3
CH

CH2

CH CH CH CH2

CH2

H3 C

H
H2C

CH CH C

H
H2C

CH CH CH CH CH3

CH CH C
O

CH

CH

CH

CH

CH2

CH2

O
NH

NH

NH2

NH2

Cl

Cl

NH2

NH2

Cl

Cl

OH

OH

OH

O
O

OH

O
O

O
Na

Na

(8) V cc cng thc cng hng v cho bit cng thc cng hng no c gi tr hn. Gii thch
H

H
C N

H
C N
H

O
H2C

O
Cng thc bn phi c gi tr hn v cc nguyn t tha cu hnh bt t.

H2C
H

Cng thc bn phi c gi tr hn v in tch dng nn nm trn nguyn t t

m in hn (carbon thay v nitrogen)

H
Cng thc gia c gi tr ln hn v cc nguyn t tha cu hnh
bt t (phn trm tn ti ln hn so vi hai dng kia)

Cng thc bn phi c gi tr ln hn v cc H C

2
nguyn t tha cu hnh bt t

CH

CH

CH2

(9) Cho bit s lai ha ca cc nguyn t carbon v nitrogen trong nhng hp cht sau:

H2C

CH

CH

CH2

2
C sp
H2N
NH2

CH3 C CH2
sp3 sp2 sp3

sp3

sp2
sp

sp3

sp3
NH
sp2
sp2

H2N
sp3

CH

CH

sp2 sp2

CH2
sp3

(10) D on v chiu v ln ca moment lng cc (nu c) ca cc phn t sau

(a) CO2 , benzene, methane, ethane, ethylene, ethylene glycol : u c cu trc i xng v trit tiu. Vy =0

(b)
;
;
(c) ng phn trans ca 1,2-dichlorethylene c =0 , trong khi ng phn cis c >0
Trong ba dng para, meta, ortho ca phn t dihydroxylbenzene, dng para c =0 , hai dng cn li c >0
(11) (a) Phn ng c xy ra gia mt acid yu (acetylene) v baz mnh (OH-) to baz yu hn (H2O)
(b) Tng t nh (a) , vi baz mnh l NaNH2 v baz yu hn ca n l NH3
(12) pKa ca tert-BuOH = 18 pKb ca tert-butoxide = -4 . Tert-butoxide l baz rt mnh trong mi trng nc, v
vy n thy phn nc theo phng trnh
t-BuO- + H2O t-BuOH + OH(13) _ BH3 l acid Lewis do cn orbital 2p trng. BH3 + NaH NaBH4
_ 1-propylene l baz Lewis do l cht i nhn. CH2=CH-CH3 + H2 C3H8
_ Acetaldehyde l acid Lewis do l cht i in t . Phn ng v d : phn ng cng bisulfite (NaHSO3)
_ C methylamine v ethanol u l cc baz Lewis . Phn ng v d : s proton ha trong dung dch acid
_ Acid acetic khng l acid Lewis cng nh baz Lewis
(14) Ta c chiu gim dn mnh acid c biu din :
Cl2CHCOOH > FCH2COOH > CH3CH2CHClCOOH > CH3CHClCH2COOH > CH2ClCH2CH2COOH > C3H7COOH
(*) Mch cng ngn th hiu ng cm cng mnh
(*) Nguyn t Chlor cng nm gn nhm carboxylic th hiu ng cm m (-I) cng mnh
(15) So snh tnh baz:
(a) EtNH2 > Et2NH > MeNH2 > NH3
[ Et = C2H5- ; Me = CH3- ]
(*) S cn tr lp th (stegic effect) lm cho tnh baz ca Et2NH yu hn EtNH2
NH2
NH2
(b)
NH2
NH2
>
>
>
NO2

OCH3

(*) Nhm methoxy (-OCH3) c

hiu ng +I lm tng hot tnh baz (tm Nitrogen) ca

aniline
(*) Nhm nitro (-NO2) nm v tr para va c -R , -I nn tnh baz gim mnh. Nu nhm nitro nm v tr
meta ch b nh hng ca hiu ng -I
(16) _ Y v Z c hydrogen linh ng nn tnh acid vt tri hn. Tuy nhin , acid Z c h cng hng carboxylic
lm cho H-acid d phn ly hn nn pKa nh hn. (xem li v d cui bi 7)
_ H ca X gn vi nitrogen nn linh ng hn H ca W, v vy pKa c nh hn cht nh.

(17)

(a) N

_ N khng b lin hp vo vng nn tnh baz mnh hn N

_ Mt khc, N va b lin hp vo vng gim tnh baz va c hydrogen linh ng N c
N H tnh acid.

(b)

NH2 _ N va b lin hp vo vng gim tnh baz va c hydrogen linh ng N c

tnh acid.
_ Gia N v N , ch c N b hiu ng cm m ca vng thm lm gim hot tnh
tm baz N c tnh baz mnh hn

N
HN

(18) (a) y l hai ng phn hnh hc cis-trans nn l hai ng phn khc nhau (s sp xp khc nhau ca cc tiu
phn dn n s phn b khc nhau ca cht, biu hin ra tnh cht ha l khc nhau)
(b) Tng t, y cng l hai ng phn do s phn b khc nhau trong khng gian ca cc nhm th trong
cacbon bn phi
H

H
O N O

HNO3 , H2SO4

(19) Sn phm l B , do :

(20) Sn phm A hnh thnh vi t l p o do s cng hng nhn thm :