hdc-b2-chuong 2-tr

I HC QUC GIA THNH PH H CH MINHTrng i Hc Khoa hc T nhin Khoa Ha B mn Ha Hc Hu c

GV. NGUYN TH THO TRN

HA HU C I CNGCHNG 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 c2.1. 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 c3.1. Theo sn 3.2. Theo nhm nh chc

TN HP CHT HU CPhn 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 CNHM 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 CNHM 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 CNHM 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 CGC 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 CGC 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 CGC 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 CGC 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 2ng 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 21. ng phn phng 1.1. ng phn v tr

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

CHNG 21. 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 21. ng phn phng1.3. S h bin Enol-ceton;amid-imid; imin-enamin; phenol-ceton; nitroso-oxim; O OH O OH

CetonO N N H N Lactam N H NH2

EnolOH 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 22. ng phn lp th2.1. 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 22. ng phn lp th2.1. 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 22. ng phn lp th2.1. 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 22. ng phn lp th2.1. 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 22. ng phn lp th 2.2. ng phn cu trngCu 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 phnCl 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 22. ng phn lp th 2.2. ng phn cu trng2.2.2. 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 vnge a a e

CHNG 22. ng phn lp th 2.2. ng phn cu trng2.2.2. Cu trng cc hp cht chi honCH3

CH3

Cu trng bn Nhm th v tr xch o c cu trng bn hnCH3 C2 H5

t-C4H9

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

CHNG 22. ng phn lp th 2.3. ng phn cu hnhng phn hnh hc v ng phn quang hc 2.3.1. ng phn hnh hc ng phn cis trans ng phn E - Z a) Alken4 3 1

H3C H

CH32

H3C H H

H CH3

H

cis-2-butenH3C H C2H5 H

H

trans-2-butenH3C H H H C2H5

Z-2-penten

E-2-penten

H

CHNG 22. ng phn lp th 2.3. ng phn cu hnh2.3.1. ng phn hnh hc b) CiclanC2H5

CH3 Cl H

C2H5

CH3 H Cl

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

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

C2H5 O2N H3 5

H1

C2H5 OH H H O2N3 5

H1

OH H

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

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

CHNG 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. 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 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. 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 22. ng phn lp th 2.3. ng phn cu hnhc) 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 gngCOOH 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 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. 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 : Sb a d R e d a b S e

CHNG 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. 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 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. ng phn quang hc Mt cht c n carbon th tnhCOOH H H OH OH COOH H OH

2n ng phn quang hcCOOH 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


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

Alen

Spiran

R1

R3

BiphenilR2 R4

CHNG 22. ng phn lp th 2.3. ng phn cu hnh2.3.2. 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-(-)-GliceraldehidCHO H OH CH2OH HgO COOH H OH CH2OH

D-(+)-Gliceraldehid

D-(-)-Gliceric acid


Hnh chiu Fisher v ng phn D v LCarbohidrat1 2 3

O C H1 2 3

O C H H C OH HO C H H C OH H C OH6 5 4

O1 2 3

C H CH2OH

O1 2 3

HO C H H C OH HO C H HO C H6 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.


Hnh chiu Fisher v ng phn D v L-Amino acidO1

O H H H H1 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 TPCH3 CH2CHCH2CH2CH3

c.

d.

Me3C

CHCH3

e.

Br

g)

CH3CHCH3 CH3

h)

CH3(CH2)7CH3

CH3 i) CH3CHCH2CH3 CH3 j) CH3CH2CCH2CHCH2CH3 CH3 CH2CH3

BI TP2. 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

hdc-b2-chuong 2-tr

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