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Chuyn bi dng HSG-----------------------------------------------------------------------Quan h cu trc v tnh cht

MI QUAN H CU TRC TNH CHT


(IM SI, TNH AXIT, TNH BAZ)
I. Mi quan h gia cu trc vi tnh axit
Mt s im cn ch khi dy v tnh axit ca cc cht
1. Khi gii thch tnh axit cn gii thch hiu ng trng thi cha phn li v c trng thi phn li.

BH+ + AV d:
AH + B

Cc ion sinh ra cng bn th tnh axit cng mnh.


V d: Xt tnh axit ca C2H5OH, C6H5OH, CH3COOH.
+

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

II. Mi quan h gia cu trc vi tnh baz


Mt s im cn ch khi dy v tnh baz ca cc cht.
1. Khi gii thch tnh baz ca cc cht cn ch trng thi u v cc trng thi to ra cation.
V d: Xt tnh baz ca NH3, CH3NH2 v CH3NHCH3.

NH3 + H2O

NH +4 + OH-

(1)
+

CH3 N H3 + OHCH3 CHNH


3 2 + H2O

(2)

CHc
CH3
3 CPhng-------------------------------------------------------------------------------------------------------------Gv: Trn
N CH3 CH CH2 CH3
N
CH3

CH3

CH3H CH2 CH2 CH2 CH3

Chuyn bi dng HSG-----------------------------------------------------------------------Quan h cu trc v tnh cht


+I
+I
+

CH3 - N H - CH3 + OHCH3 - NH - CH3 + H2O

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

CH3NH2 > NH3.


2. Trong phn t nu c cha nhm y e s lm tng tnh baz, ngc li nhm ht e s lm gim tnh baz ca
hp cht.
V d: Tnh baz gim dn theo chiu:
CH3 CH2 NH2 > CH3 NH2 > NH3 > C6H5 NH2 > C6H5 NH C6H5
3. Amin bc 2 c tnh baz ln hn amin bc 1 v amin bc 3.
4. Tnh baz ca amin d vng no ln hn amin d vng thm.
V d: Tnh baz gim dn theo chiu:
sp3 >

sp2

>

sp

III. Mi quan h gia cu trc vi nhit si ca cc cht.


- Nhit si ca cc cht ph thuc vo: phn t khi, lin kt hidro lin phn t v lc Vanevan.
- Ta xt nhit si ca mt s hirocacbon v dn xut ca hirocacbon.
1. Nhit si ca hirocacbon
a. Ankan
- Nhit si ch yu ph thuc vo lc Vanevan.
+ Khi phn t khi (M) tng th nhit si tng
V d: nhit si ca C3H8 > C3H6.
+ phn nhnh trong ankan cng tng th lc Vanevan gim nn nhit si gim.
V d: Nhit si tng theo chiu:
neopentan
<
isopentan
< pentan
+ S ng vng lm cho nhit si tng.
V d: nhit si: CH3 CH2 CH2 CH2 CH2 CH3 <
(690C)

(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:

t s0 : CH2=CHCH=CH2CH3 > CH2=CHCH2CH=CH2


(420C)

(260C)

2. Nhit si ca cc dn xut ankan


a. Dn xut RX khng c lin kt hidro
phn cc ca cc phn t (momen lng cc) cng ln th nhit si cng cao.
V d: Hp cht:
C6H14
C4H9Cl
C4H9CHO
C3H7NO2

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

<

CH3 CH2 CH CH3 < CH3CH2CH2CH2Cl


Cl

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

Chuyn bi dng HSG-----------------------------------------------------------------------Quan h cu trc v tnh cht

CH3 CH CH3

< CH3CH2CH2CH3 <

CH3

CH3 N CH3
CH3

< CH3CH2CH2NH2 <

< CH3CH2CH2OH < CH3CH2COOH.


d. Cc amin
+ Nhit si ca cc amin bc 2 > nhit si ca amin bc 3.
V d:

t s0 (CH3)2NH > (CH3)3N

(70C)
(30C)
+ Nhit si ca amin a chc > amin n chc.
V d:

t s0 H2NCH2CH2NH2 > CH3CH2CH2NH2.

(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

. Hy in gi tr pKa vo cc nhm COOH.

Bi 5:
a. Hy sp xp theo chiu tng dn

t s0 (c gii thch) ca dy sau: C6H5C2H5 (A), C6H5CH2OH (B), C6H5O

CH3 (C), C6H5CH=O (D), C6H5COOH (E).


b. Trong 5 cht trn c 1 cht trng thi rn (nhit thng) v mt cht lng dn dn ha rn khi ngoi
khng kh. Hy cho bit 2 cht trn v gii thch, nu phng php bo qun cht lng nu.
c. Trong 5 cht trn th nhng cp cht no c th tc dng c vi nhau (iu kin phn ng c ). Vit
phng trnh phn ng.

Gv: Trn c Phng--------------------------------------------------------------------------------------------------------------

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