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BH+ + AV d:
AH + B
C2 H 5 O- + H3O+ (1)
C2 H5 O H + H2O
+I
+I
gg
OH
+ H 2O
gg
+
O- + H3O (2)
C, I
C, I
H+ H2O
CH3 C
O
O- CH3
CH3 C
O
1
2
1
2
C
O
+ H3O+ (3)
C, I
Nhn xt: bn ca cc ion (1) < (2) < (3) do tnh axit ca C2H5OH < C6H5OH < CH3COOH.
2. Trong bt k trng hp no, nu c nhm th ht e s lm cho tnh axit tng. Ngc li, nu c nhm th
y e s lm cho tnh axit gim.
V d: Tnh axit ca cc cht tng dn trong dy sau:
CH3CH2CH2COOH < CH3CHBrCH2COOH < CH3CH2CHBrCOOH <
< CH3CHICHBrCOOH < CH3CHBrCHBrCOOH.
3. Tnh axit ca axit khng no v axit thm ln hn axit no tng ng.
V d 1: Tnh axit tng dn theo dy sau:
CH3CH2CH2COOH < CH3CH=CHCOOH < CH3CCCOOH.
V d 2: Tnh axit ca
COOH >
COOH
Trong axit cha lin kt i C=C th tnh axit ca dng cis > tnh axit ca dng trans.
CH3
OH
<
CH3
C
H
C O
C O
C
H
H
OH
I lm Ka tng, +C tng lm Ka gim I lm Ka tng, +C gim lm Ka tng
4. Cc dng axit , khng no c tnh axit mnh hn dng , khng no.
V d: Tnh axit:
CH 3 C = C
I v + C
C< = O
C H 2 = C H CH 2 C = O
OH
ch c I
OH
NH3 + H2O
NH +4 + OH-
(1)
+
(2)
CHc
CH3
3 CPhng-------------------------------------------------------------------------------------------------------------Gv: Trn
N CH3 CH CH2 CH3
N
CH3
CH3
2
+I mnh
(3)
+I mnh
+
V bn cc cation gim theo chiu: CH 3 - N H -CH3 > CH3- N H > NH 4 nn tnh baz ca CH3NHCH3 >
2
sp2
>
sp
(810C)
b. Anken v polien
+ Trong anken th nhit si ca dng cis > nhit si ca dng trans.
+ Cc polien lin hp c nhit si > cc polien khng lin hp.
V d:
(260C)
0
1,86
2,49
3,15
t s0 (0C)
690
780
1030
1310
b. Phn t RX c bc R cng tng th nhit si cng gim, do i xng cu tng, lc Vanevan gim nn
nhit si gim.
V d: Nhit si tng trong dy sau:
CH3
CH3
C CCl
CH3
<
CH3
CH CH2 Cl
CH3
<
c. Hp cht RX c lin kt hidro lin phn t c nhit si ln hn hp cht khng c lin kt hidro lin
phn t, lin kt hidro lin phn t cng bn th nhit si cng tng.
V d: Nhit si tng theo chiu:
Gv: Trn c Phng-------------------------------------------------------------------------------------------------------------- 2
CH3 CH CH3
CH3
CH3 N CH3
CH3
(70C)
(30C)
+ Nhit si ca amin a chc > amin n chc.
V d:
(1170C)
(490C)
V s nhm to lin kt hidro lin phn t cng tng th s lin kt hidro tng nn nhit si tng.
e. Cc amit
+ Amit bc 1 (khng th) c nhit si cao hn amit (N.th).
V d:
O
O
C NH2 >
t s0
C N(C2H5)2 >
CH3 C NH2
O
Mt s bi tp tham kho
Bi 1: So snh v gii thch tnh axit trong dy.
a. CF3 [CH2]n COOH vi n = 0, 1, 2, 3.
b.
X
COOH vi X : H, Cl, CH3, OCH3, NO2.
Bi 2: Sp xp theo trnh t tng dn tnh baz ca cc cht sau:
a. CH3CH2NH2 (A),
(B), CH2=CHCH2NH2 (C).
b. C2H5NH2, NH3, CH3NH2, CH2=CHCH2NH2, C6H5NH2, CH3NHC6H5, (CH3)2NH, (C6H5)2NH.
Bi 3: Vitamin C c cng thc:
6
CH2OH
H 5 OH
OH
pKa = 4,21.
OH
Ti sao Vitamin C c tnh axit. Nu cho 1 mol Vitamin C tc dng vi 1 mol NaOH th phn ng xy ra nhm OH
no?
Bi 4: Cho axit v cc gi tr pKa nh sau: 4,76 ; 3,13 ; 6,40.
OH
HOOC CH2 C CH2 COOH
COOH
Bi 5:
a. Hy sp xp theo chiu tng dn