I HC QUC GIA THNH PH H CH MINH

Trng i Hc Khoa hc T nhin Khoa Ha B mn Ha Hc Hu c

GV. NGUYN TH THO TRN

HA HU C I CNG
CHNG 1: I CNG V HA HC HU C CHNG 2: NG PHN CHNG 3: C CU IN T CHNG 4: HIDROCARBON CHNG 5: HALOGENUR ALKIL, HP CHT GRINARD CHNG 6: ALCOL, PHENOL, ESTER CHNG 7: ALDEHID, CETON CHNG 8: ACID CARBOXILIC V CC DN XUT CHNG 9: AMIN V CC MUI DIAZONIUM CHNG 10: ACID AMIN, HIDRATCARBON, TRIGLICERID CHNG 11: CC HP CHT D HON

GIO TRNH

CHNG 1 : I CNG V HA HC HU C

1. Tnh cht chung ca cc hp cht hu c 2. Xc nh c cu hp cht hu c

2.1. C lp v tinh ch 2.2. Xc nh cng thc phn t 2.3. Xc nh cng thc cu to

3. Phn loi cc hp cht hu c

3.1. Theo sn 3.2. Theo nhm nh chc

TN HP CHT HU C
Phn t hu c: dy chnh (bao gm nhm th) v nhm chc ha hc

NHM CHC HA HC - Cc hp cht hu c c cng hot tnh ha hc: cng nhm chc - To tnh cht ha hc c th cho phn t hu c m n hin din

-Hp cht n chc: ch mang mt nhm chc -Hp cht a chc: c cha t 2 nhm chc tr ln (nhm chc c th ging hoc khc nhau)

TN HP CHT HU C
NHM CHC HA HC Cc nhm chc ha hc v danh php Cu trc R-H R-CH=CR-C C-R Nhm chc Alkan Alken Alkin Aren Halogenur Alcol Eter Amin Nitril Tip u ng Alkil Alkenil Alkinil Halogeno Hidroxi Oxid alkil alkil Amino Ciano Tip v ng -an -en -in -en Ol Alkil eter -amin -nitril -carbonitril

R-C6H5 C-X (X = F; Cl; Br; I) C-OH R-O-R R-NH2 R-C N

TN HP CHT HU C
NHM CHC HA HC Cc nhm chc ha hc v danh php Cu trc R-NO2 R-S-R R-SO-R R-SO2-R R-SH R-S-S-R R-CH=O R-CO-R R-CO-OH Nhm chc Nitro Sulfur; Tioeter Sulfoxid Sulfon Tiol Disulfur Aldehid Ceton Acid carboxilic Tip u ng Nitro Alkiltio Mercapto Oxo; formil Oxo Carboxi Alkil sulfur sulfoxid Sulfon -tiol -disulfur -al -carbaldehid -on Acid ic (oic) Acid carboxilic Tip v ng

TN HP CHT HU C
NHM CHC HA HC

Cc nhm chc ha hc v danh php Cu trc R-CO-X (X = halogen) R-CO-O-R R-CO-NH2 R-CO-O-CO-R R-C=NEster Amid Anhidrid acid Imin Alcoxi carbonil Carbamoil Amido Imino Nhm chc Halogenur acid Tip u ng Halogeno carbonil Tip v ng Halogenur il Halogenur oil Halogenur carbonil oat alkil -carboxilat alkil -amid -carboxamid Anhidrid oic Anhidrid carboxilic Imin

TN HP CHT HU C
GC Gc alkil: tn cng l -il Chi phng: - Bo ha: metil, etil, n-propil, i-propil, n-butil, metilen (-CH2-) - Bt bo ha: vinil hay etenil (-CH=CH2), alil hay 2-propenil (-CH2-CH=CH2), metiliden (=CH2), metilidin ( CH), viniliden (=C=CH2),

Chi hon (n hon): ciclohexil (-C6H11) Hng phng: phenil (-C6H5), benzil (-CH2-C6H5), benziliden (=CH-C6H5),

TN HP CHT HU C
GC Gc oxigen hoc gc c cha oxigen -O-R: Alkoxi (O-CH3: metoxi; O-CH2-CH3: Etoxi; ) -OH: Hidroxi -O-C6H5: Phenoxi; pheniloxi -O-CH2-C6H5: Benziloxi -CO-R: Alkanoil -CO-H: Metanoil; formil -O-C6H5: Phenoxi; pheniloxi -CO-O-R: Alkoxi carbonil -CO-CH3: Metoxi carbonil

TN HP CHT HU C
GC Gc nitrogen -NH2: Amino -NH-CH3: N-Metilamino -N(CH3)2: N,N-Diemtilamino - N(CH3)(CH2-CH3): N-Etil-N-metilamino -C N: Ciano -NO2:Nitro =N-C6H5: Phenilimino =N-OH:Hidroxiimino =N-NH2: Hidrazono -N=N-CH3: Metilazo

TN HP CHT HU C
GC Gc halogen -Cl: Cloro -Br: Bromo -I: Iodo Gc lu hunh -S-: Tio -SH: Mercapto -S-R: Alkiltio (-S-C6H5: Pheniltio) -S-S-R: Alkilditio -SO-R: Alkilsulfinil -SO2-R: Alkilsulfonil

CHNG 2 : TNH NG PHN

ng phn l nhng hp cht c cng cng thc phn t nhng cng thc khai trin khc nhau.

CHNG 2
ng phn

ng phn phng

ng phn lp th

P v tr

P cu to

H bin

P cu hnh

P cu trng

P hnh hc

P quang hc

P cis (Z)

P trans (E)

CHNG 2
1. ng phn phng 1.1. ng phn v tr

- Cng CTPT - Cng nhm chc - Khc sn carbon hoc khc v tr nhm chc

CHNG 2
1. ng phn phng

1.2. ng phn cu to
( = 1)
C 4H 8 O CH3CH CHCH2OH 2-Butenol OH Ciclobutanol CH3CH2CH2-CHO Butanal CH2OH Hidroximetilciclopropan H3C O CH3CH2CCH3 Butanon O CH3 O Tetrahidrofuran

1,2-Dimetiloxiran

- Cng CTPT - Khc nhm chc

CHNG 2
1. ng phn phng
1.3. S h bin Enol-ceton;amid-imid; imin-enamin; phenol-ceton; nitroso-oxim;
O OH O OH

Ceton
O N N H N Lactam N H NH2

Enol
OH N N H Guanin N N NH2

Lactimin

S chuyn i thun nghch gia hai ng phn cu to, do di chuyn ca mt nhm nguyn t hoc thng nht l ca hidrogen t v tr ny n v tr khc trong cng 1 phn t

ng phn

ng phn phng

ng phn lp th

P v tr

P cu to

H bin

P cu hnh

P cu trng

P hnh hc

P quang hc

P cis (Z)

P trans (E)

CHNG 2
2. ng phn lp th
2.1. Cng thc lp th 2.1.1. Thuyt carbon t din

a C d b e

C tp chng sp3

Vn o sp3(1 vn o 2s v 3 vn o 2p): s kt hp ca cc vn o 2s1 2px1 2py1 2pz1ca C

Cch biu din phn t hp cht hu c trong khng gian: - Cng thc phi cnh - Cng thc chiu Newman - Cng thc chiu Fisher

CHNG 2
2. ng phn lp th
2.1. Cng thc lp th 2.1.2. Cng thc phi cnh: thng biu din cho hp cht chi phng

Ni C-a v C-b trong mt phng Ni C-d hng ra ngoi mt phng Ni C-e hng ra sau mt phng

2.1.3. Cng thc chiu Newman Cho bit v tr tng i ca cc ni ca 2 nguyn t k nhau

CHNG 2
2. ng phn lp th
2.1. Cng thc lp th

2.1.4. Cng thc chiu Fischer

2 ni thng ng: hng ra sau mt phng 2 ni nm ngang : hng ra trc mt phng

Qui c: - Dy chnh: trc thng ng vi carbon u dy c oxi ha cao c t nh ca trc (cc nhm th c so snh u tin theo qui tc Cahn-IngoldPrelog).

CHNG 2
2. ng phn lp th
2.1. Cng thc lp th 2.1.5. Chuyn i t cng thc phi cnh sang cng thc chiu Fischer

CH3 H HO H COOH

CH3 OH COOH OH

CH3 COOH H HOOC

CH3 OH OH

Cl Br H

H Cl C2 H5 Br

C2H5 H H CH3 H H

CH3 Br Cl C2 H5

CH3

Tri qua

Phi qua

CHNG 2
2. ng phn lp th 2.2. ng phn cu trng
Cu trng l cc dng khc nhau ca mt cu hnh, chng c c l do s quay quanh mt ni n 2.2.1. Cu trng cc hp cht phi hon - Cu trng lch: cu trng bn lch v cu trng i lch - Cu trng che khut : che khut ton phn v che khut mt phn
Cl H H Cl H H Cl H H H H H H Cl H Cl H H Cl Cl H H H H H Cl Cl H H Cl Cl H Cl H H H Cl H Cl H H Cl

H H

H H

Cl H

i lch

Bn lch

Che khut ton phn Che khut mt phn

CHNG 2
2. ng phn lp th 2.2. ng phn cu trng
2.2.2. Cu trng cc hp cht chi hon

Cu trng gh

Cu trng tu

Cu trng tu xon

e (equatorial) : ni xch o a (axial) : ni trc : ni hng xung mt phng trung bnh ca vng : ni hng ln mt phng trung bnh ca vng
e a a e

CHNG 2
2. ng phn lp th 2.2. ng phn cu trng
2.2.2. Cu trng cc hp cht chi hon
CH3

CH3

Cu trng bn Nhm th v tr xch o c cu trng bn hn

CH3 C2 H5

t-C4H9

Nhm th ln u tin v tr xch o Nhm t-butil lun v tr xch o

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
ng phn hnh hc v ng phn quang hc 2.3.1. ng phn hnh hc ng phn cis trans ng phn E - Z a) Alken
4 3 1

H3C H

CH3
2

H3C H H

H CH3

cis-2-buten
H3C H C2H5 H

trans-2-buten
H3C H H H C2H5

Z-2-penten

E-2-penten

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.1. ng phn hnh hc b) Ciclan
C2H5

CH3 Cl H

C2H5

CH3 H Cl

cis-1-Cloro-3-etil-3-metilciclohexan

trans-1-Cloro-3-etil-3-metilciclohexan

C2H5 O2N H
3 5

H
1

C2H5 OH H H O2N
3 5

H
1

OH H

c-3-Etil-c-5-nitrociclohexan-r-1-ol

c-3-Etil-t-5-nitrociclohexan-r-1-ol

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc Mt hp cht c tnh quang hot khi c tnh khng i xng gng. - Khng c mt phng i xng - Khng c tm i xng a) Tnh quang hot : tnh cht lm xoay mt phng nh sng phn cc phng mt gc . Cht t trin: lm quay mt phng nh sng phn cc v bn tay tri K hiu : (-) hoc l Cht hu trin: lm quay mt phng nh sng phn cc v bn tay phi K hiu : (+) hoc d

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc

Sx

Dung dch [ ] Cht lng

t D

100 = = lc lc '

[ ]tD

ld

: gc quay quan st (nng lc trin quang) l : di ng cha mu c : nng dung dch (g/ml) ; c : g/100ml) d : t trng cht lng tinh cht (g/ml) T : nhit khi o (C) D : nh sng n sc ca n natrium ( = 589 nm)

b) Carbon th tnh: carbon phi i xng - carbon mang 4 nhm th khc nhau K hiu : C*

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
c) ng phn quang hc Nhng hp cht c cng cng thc khai trin trong mt phng nhng cng thc lp th khc nhau - i phn (i hnh ) : cng thc lp th i xng nhau qua gng phng - Xuyn lp th phn (bn i hnh) : CTLT khng i xng nhau qua gng
COOH COOH HO CH3 H H CH3 COOH OH H OH OH H COOH H H COOH OH OH COOH

Hai i phn ca acid lactic

Hai xuyn lp th phn ca acid tartric

Cc ng phn quang hc c ho tnh v l tnh ging nhau Tnh quang hot khc nhau do hot tnh sinh hc khc nhau

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc d) Xc nh cu hnh tuyt i: R - S (R : rectus, phi ; S : sinister, tri) - Cu hnh tuyt i: cu hnh thc s ca phn t trong khng gian

ng phn quang hc c cha C th tnh : C*abde

- Xp cc phi t a, b, d, e theo th t u tin da vo quy tc chui (a > b > d > e) - Quan st vin nhn C* theo chiu t C* n phi t c u tin thp nht - Xc nh chiu i t a n b ri n d. Nu chiu quay theo chiu kim ng h : R ngc chiu kim ng h : S
b a d R e d a b S e

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc Quy tc chui - Da theo bc s nguyn t : -I > -Br > -Cl > SH > -OH >-NH2 > -CH3 > -H - ng v c khi lng ln th u tin hn : 18O >17O >16O hay T > D > H - Ni ba > Ni i > Ni n (nguyn t mang ni a c xem tng ng vi nguyn t mang s lng ni n tng ng). - i in t t do c u tin thp nht - cis > trans, Z > E, R > S

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc Mt cht c n carbon th tnh
COOH H H OH OH COOH H OH

2n ng phn quang hc
COOH OH H COOH HO H COOH H OH COOH

Acid meso-tartric

Acid (+)-tartric

Acid (-)-tartric

i vi hp cht c 2 tm C th tnh, dng meso c tm thy ch khi 4 nhm gn trn C th tnh ny ging ht 4 nhm gn trn C th tnh cn li.
Y A A Z B B B B Y A A Z A B Z Y B A B A Y A B Z

eritro

treo

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc

ng phn quang hc khng cha C th tnh : trong trng hp ca alen, spiran v biphenil

Alen

Spiran

R1

R3

Biphenil
R2 R4

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc e) Xc nh cu hnh tng i: D & L - Cu hnh tng i: cu hnh c suy ra t cu hnh tuyt i theo nhng quy tc v lp th.
CHO H OH CH2OH HO CHO H CH2OH

D-(+)-Gliceraldehid

L-(-)-Gliceraldehid
CHO H OH CH2OH HgO COOH H OH CH2OH

D-(+)-Gliceraldehid

D-(-)-Gliceric acid

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc

Hnh chiu Fisher v ng phn D v L

Carbohidrat
1 2 3

O C H
1 2 3

O C H H C OH HO C H H C OH H C OH
6 5 4

O
1 2 3

C H CH2OH

O
1 2 3

HO C H H C OH HO C H HO C H
6 5 4

HO C H

C H CH2OH

H C OH
(D-Gliceraldehid)

(L-Gliceraldehid)

CH2OH

CH2OH

L-Glucose

D-Glucose

Nhm OH gn ln carbon bt i xng c s th t nh v ln nht quay sang phi l ng phn D, ngc li l ng phn (i phn) L.

CHNG 2
2. ng phn lp th 2.3. ng phn cu hnh
2.3.2. ng phn quang hc

Hnh chiu Fisher v ng phn D v L

-Amino acid
O
1

O H H H H
1 2 3 4

C C

C C C

H NH2 H

Nhm NH2 gn ln carbon bt i xng c s th t nh v nh nht quay sang phi l ng phn D, ngc li l ng phn (i phn) L.

H 2N

2 3

C H 2O H

C 6H 5

L-Serin

D-Phenilanalin

Cm n cc bn lng nghe

1. Gi tn cc hp cht sau y a. b.

BI TP
CH3 CH2CHCH2CH2CH3

c.

d.

Me3C

CHCH3

e.

Br

g)

CH3CHCH3 CH3

h)

CH3(CH2)7CH3

CH3 i) CH3CHCH2CH3 CH3 j) CH3CH2CCH2CHCH2CH3 CH3 CH2CH3

BI TP
2. Viet c cau cac hp chat sau ay: a) 2,3-Dimetilbutan b) 2,2-Dimetilpropan c) 3,4-Dimetilheptan d) 2,4-Dimetil-4-etilheptan e) 1,7-Dibromo-4-(2-cloroetil)heptan f) 1-Cloro-2-iodo-3-ciclopropilpentan g) 1,1-Dietil-2-metilciclohexan 3. Ve c cau tat ca nhng ong phan cua C5H12. Cho biet ten theo IUPAC cua nhng hp chat nay.

NHT K Th 4-ngy 17 thng 03 nm 2010

1. Tng Vy MSSV: 0917418 2. Trn Nht Thanh: MSSV: 0917297