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TRNG I HC QUC GIA TP- H CH MINH

TRNG I HC KHOA HC T NHIN
SEMINAR C CH PHN NG HU C
ti:
PHN NG CNG NC, ALCOHOL
VO AlDEHYDE VA KETONE
Nhm 2
HVTH: BI TH THU HNG
TRN TH HUYN TRANG
PHAM NGOC N
GVHD: TS. L VIT TIN
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NI DUNG
Phn ng cng nc
(H
2
O)

2
Phn ng cng alcohol
(ROH)

3
Phn ng cng vo C=O
1
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Trong hp cht carbonyl, lin kt C=O lun lun phn cc v pha
O, to nn hai tm phn ng: tm chiu tac kich thn hch trn C,
va tm chiu tac kich thn in t trn O.

+ Nguyn t Oxygen cho phn ng theo kiu cho nhn in t
nn phn ng xy ra nhanh v lin kt khng bn nn khng dn
n sn phm.

+ Phn ng trn Carbon thng xy ra trong giai on chm ca
phn ng (giai on quyt inh tc phn ng) va lin kt to
thnh bn dn to ra sn phm phn ng.
Do phn ng c trng ca nhm C=O la phn ng cng
thn hch.

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1.PHN NG CNG VO C=O.
C O
C
O
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C ch chung cho phn ng cng Nucleophile vao hp
cht carbonyl
+
-
1.PHN NG CNG VO C=O.
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Nc l cht thn hch yu nn phn ng cng H
2
O vo
aldehyde hay ketone xy ra chm v thun nghich cho ra
hydrat hay gem-diol.
Do c hai nhm OH gn trn cung mt carbon nn cac hp
cht gem-diol khng bn, nm trong trng thai thun nghich
vi cht u.
2. PHN NG CNG H
2
O: phn ng hydrat ha
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Trng thai cn bng phu thuc vao cu truc ca aldehyde,
ketone va phn ln la phu thuc vao cu truc hydrat.
2. PHN NG CNG H
2
O: phn ng hydrat ha
Formaldehyde, aldehyde va ketone mang nhm th rut in
t, trong dung dich chng hu nh dng hydrat.
Th d :
C
H H
O
+ H
2
O
C
OH
OH
H
H
Formandehyde 0,1% Formandehyde hydrate 99,9%
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2. PHN NG CNG H
2
O: phn ng hydrat ha
Th d :
Cl
3
CCHO + HOH
Cl
Cl
Cl H
O
O
Ph
Ph
O
O
O + HOH
Ph
Ph
O
O
O
O
H
.
.
.
H
.
.
.
H
H .
.
.
...
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Acetone gn nh khng cho hydrat.
Khi cho acetone trn vi H
2
O
18
nhn thy nng acetone cha
O
18
tng dn theo thi gian.
2. PHN NG CNG H
2
O: phn ng hydrat ha
O
+ H
2
O
18
OH
H
3
C
CH
3
O
18
H O
18
H
2
O
+
H
3
C
H
3
C
H
3
C
H
3
C
C
O
CH
3
+
H
2
O
H C
OH
CH
3
H
OH
58
%
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2. PHN NG CNG H
2
O: phn ng hydrat ha
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Vai tr ca cht xc tc acid l hot ha nhm carbonyl lm cho in
tch dng nguyn t carbon carbonyl tng ln v do tc nhn
Nucleophile H
2
O d tn cng vo.
2. PHN NG CNG H
2
O: phn ng hydrat ha
Xc tc acid
V H
2
O l cht thn hch yu nn phn ng cng H
2
O vo aldehyde
hay ketone xy ra chm v thun nghch. Phn ng xy ra nhanh hn
khi c xc tc acid hoc base.
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2. PHN NG CNG H
2
O: phn ng hydrat ha
C ch xuc tac
acid c bit
HA
O HA
O H
HOH
OH
OH
2
+ A
OH
O
OH
OH
O
- H
+
A
+
slow
H
H
Gem hay diol
C ch xuc tac
acid chung
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Ion hydroxide c tnh thn hch mnh hn nc, phn ng vi
nhm carbonyl nhanh hn nc.
2. PHN NG CNG H
2
O: phn ng hydrat ha
Xc tc base
OH
HOH
OH
OH
O
+
slow
O
OH
OH +
C ch
xc tc
baz c
bit
C ch
xc tc
baz
chung
HOH
OH
OH
O
slow
OH +
B
-
+ HOH
O
OH
BH +
+
BH
OH +
B
-
+ H
2
O
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3. PHN NG CNG ALCOHOL (ROH)
3.1. Cng alcohol vao Aldehyde
Alcohol cng vao aldehyde cho sn phm la hemiacetal va
acetal.

Cung nh nc, alcohol la cht thn hch yu nn phn
ng cng thn hch alcohol vo hp cht carbonyl xy ra
kho khn va thun nghich.
H
3
C
H
OH
O
H
H
3
C
CH
3
OH
+
H
+
hay HO
-
OCH
3
Hemiacetal
Acetal
H
2
O +
H
3
C
H
OH
CH
3
OH
+
H
+
OCH
3
H
3
C
H
OCH
3
OCH
3
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- Hemiacetal: to ra khi cho 1 phn t aldehyde cng vi
1 phn t alcohol.

Hemiacetal khng bn, thng khng tach ra khoi hn
hp do nm cn bng vi cht u.

Tng t nh trong phn ng cng nc, C cu
aldehyde cung nh hng n kh nng phn ng, hng
s cn bng thp hn phn ng cng nc.

Xuc tac base hoc acid lam tng tc phn ng.
3. PHN NG CNG ALCOHOL (ROH)
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Trong mi trng base: ion alkoxide (RO
-
) c to ra la
cht thn hch mnh hn so vi alcohol (ROH), nn phn
ng cng xy ra nhanh hn.
3. PHN NG CNG ALCOHOL (ROH)
R
1
C H
O
OR
2
R
1
C H
O
OR
2
OR
2 +
R
1
C H
OH
OR
2
HOR
2
,
-
. .
.
.
. .
. .
.
.
. .
.
.
.
.
. .
. .
. .
. .
.
.
.
.
+ OH
+
HOH OR
2
O H R
2
.
.
.
.
.
.
.
.
.
.
.
.
.
.
C ch :
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Trong dung dich acid: proton hot ha nhm carbonyl
lam tng tc phn ng.

C ch:
3. PHN NG CNG ALCOHOL (ROH)
. .
R
1
C H
O
R
1
C H
OH
O
-
R
1
C H
OH
OR
2
+
H
R
1
C H
OH
HOR
2 H
H
R
2
. .
.
.
. .
. .
. .
.
.
. .
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Nu nng xc tc H
+
cao, alcohol c th bi proton ha
to ra ion oxonium lam mt tinh thn hch.
Lm gim nng tc nhn nucleophil ROH
lm chm tc phn ng.

3. PHN NG CNG ALCOHOL (ROH)
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-Acetal: Trong mi trng acid mnh, hemiacetal phn ng vi
mt phn t alcohol cho ra acetal.
Hemiacetal bi proton ha thanh ion hydroxonium, ion nay mt 1
phn t nc thanh ion alkyloxonium. Ion nay bn do cng
hng vi O, s cng 1 phn t alcohol vao ion alkyloxonium
cho acid lin hp ca acetal.
3. PHN NG CNG ALCOHOL (ROH)
R
1
C H
OH
2
OR
2
R
1
C H
OH
OR
2
H
+
- H
2
O
R
1
C H
OR
2
R
1
C H
OR
2
.
.
. .
. .
. .
.
.
.
.
. .
.
.
. .
. .
R
1
C H
OR
2
R
1
C H
OR
2
R
1
C H
OR
2
ROH
O H R
-H
+
OR
. .
.
.
. .
. .
.
.
. .
.
. . .
.
.
.
.
. .
C ch:
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Acetal la hp cht bn, c th c lp sau khi trung hoa
hn hp phn ng, va tinh ch. Acetal d dang bi thy
phn bng dung dich acid loang thanh aldehyde ban
u. C ch thy phn tng dng nh c ch to
acetal nhng theo th t ngc li.

cn bng chuyn dich sang phi: dung lng tha
alcohol, hoc ct loi nc ra khoi phn ng.

2. PHN NG CNG ALCOHOL (ROH)
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3. PHN NG CNG ALCOHOL (ROH)
3.2. Cng alcohol vao ketone:
Ketone cho phn ng cng vi alcohol to hemiketal va
ketal. Do ketone c hot tinh vi tac cht thn hch kem
hn aldehyde nn s cng alcohol kho khn hn. C ch
phn ng xy ra tng t nh vi aldehyde.
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3. PHN NG CNG ALCOHOL (ROH)
Ha hc lp th: trong phn ng to hemiacetal
-Formaldehyde: to thnh mt sn phm.
-Nu R1 khc H: Sn phm to thnh l hn hp hai
ng phn quang hoc (i phn hoc xuyn lp th
phn).

R
1
C H
OH
OR
2
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3. PHN NG CNG ALCOHOL (ROH)
Ha hc lp th: trong phn ng to hemicetal
-Nu R1 ging R2 : to thnh mt sn phm.
-Nu R1 khc R2: Sn phm to thnh l hn hp hai
ng phn quang hoc (i phn hoc xuyn lp th
phn).

Cc aldehyde v ketone mang nhm rt in t d dng
cho ra hemiacetal v hemiketal nhng rt kh khn to
thnh acetal v ketal.
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NG DNG: bo v nhm C=O
- Phng php ny dng bo v nhm chc andehyde
hay ketone, sau ti to li bng phn ng thy phn trong
mi trng acid.
O
O
OCH
2
CH
3
HOCH
2
CH
2
OH
Acid catalyst
O O
OCH
2
CH
3
O
+ H
2
O
HOCH
2
CH
2
OH
O
CH
2
OH
O O
CH
2
OH
Ethyl 4-oxopentanoate
5-hydroxy-2-pentanone
+ CH
3
CH
2
OH
H
3
O
+
+
1.LiAlH
4
2. H
3
O
+
Khng th phn
ng trc tip
3. PHN NG CNG ALCOHOL (ROH)
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