Hợp chất carbonyl và dẫn xuất acid ceton
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ALDEHYD VAØ CETON BEÙO
1
1. Goùi teõn caực hụùp chaỏt sau:
CCl3 CHO
Tricloroetanal
Tricloroacetaldehyd
Cloral
CH2 CH CHO
Propenal
Acrolein
(CH3) 2 C CH CH2 CO CH3
5-methyl-4-hexen-2-on
CH3 CO CH2 CO CH3
2,4-pentandion
Acetoaceton
CH3 CH CH CHO
2-butenal
Crotonaldehyd
OHC CHO
Etandial
Glyoxal
CH3 CO CH CH2
C6H5 CH2 CH2 CHO
Methylvinylceton
3-phenylpropanal
CH3 CH(OCH3) 2
1,1-dimethoxyetan
CH3 CO CH2 CHO
3-oxobutanal
Acetoacetandehyd
2
O
HO
OH
OCH3
OCH3
2,6-di-(4'-hydroxy-3'-methoxybenzyl)cyclohexanon
cyclovalon(thuoác lôïi maät)
Cl
NH CH3.HCl
O
2-(2'-clorophenyl)-2-(methylamino)cyclohexanon
Ketamin
1'
O HO CH3
1
6
2'
6-[(R) -2'-hydroxy-6'methylhept-5'-en-2'-yl) cyclohex-2-enon
Hermandulcin
3
2. Vieát coâng thöùc caùc chaát sau:
a.
(CH 3) 3C C C (CH 3) 3
O
O
b.
cyclopropanon
Di-tert-butylceton
d.
CH3
c.
CH2 C CH2CH3
O
O
ethylbenzylceton
3-methyl-3 cyclohexen-1-on
f.
e.
CH2CHO
phenylacetaldehyd
CH2CH3
g.
CH2 CH CH2 C CHO
CH3
methylethylallylacetaldehyd
CH 3
Cl
C CH CH CHO
CH3
4-cloro-4-methylpenten-2-al
h.
CH 3 CH 2 CH 2 C CH 2 CHO
O
3-oxohexanal
4
3. Aldol hoùa:
a.
CH3 CH CH CHO
CH3 CH2 CHO
+ CH3 CHO
HO
CH3 CH C CHO
-
CH3
H2O
CH3 CH2 CH CH CHO
CH3 CH2 CH C CHO
CH3
b.
HCHO +
CH3 CH2 CHO
HO
H2O
-
H2C C CHO
CH3
5
4. Vieát caùc quaù trình chuyeån hoùa
a. Propen aceton
HCl
CH3CH CH2
CH3 CH CH3
HO
Cl
CH 3 CH CH 3
[O]
OH
CH3 C CH3
O
b. 1-bromobutan methylethylceton
CH3CH2CH2CH2Br
+
H2O/H
KOH/alcol
HBr
CH3 CH 2 CH CH3
OH
CH 3CH 2CH CH 2
[O]
CH3 CH2 C CH3
O
6
4.
c. Propen propanal
CH 3 CH CH 2
H2O
peroxyd
CH 3 CH 2 CH 2 OH
CuO
CH 3 CH 2 CHO
d. Cyclohexen cyclohexanon:
HCl
Cl
HO
OH
[O]
O
7
5. Ñieàu cheá butanon:
a.
CH3 CH2 CH CH3
[O]
NaOH
Cl
2-clorobutan
CH3 CH2 C CH3
O
Butanon
b.
CH 3 CHO
[H]
NaBH4
hoaë c H2/Ni
1)CH3CHO
+
2)H2O/H
CH 3 CH 2OH
PCl5
CH3 CH2 CH CH3
OH
CH 3 CH 2Cl
[O]
Mg
ether khan
CH 3 CH 2MgCl
CH3 CH2 C CH3
O
Butanon
8
5.
c.
CH3 CH CH CH3
Cl
d.
Cl
CH3 C N
Acetonitril
H2O/H
CH3 C C2H5
2 H2O/H
hoaë c 2 KOH/alcol
C2H5MgBr
+
2-buten
Zn
NMgBr
+
[O]
CH3 CH2 C CH3
O
Butanon
CH3 CH2 C CH3
O
Butanon
9
5.
e.
1-Buten
+
H2O/H
2-Butanol
[O]
Butanon
f.
CH3 CH2 CH CH CH3
CH3 OH
H2SO4
0
180 C
CH3CH 2C CHCH3
CH3
3-methyl-2-pentanol
[O]
KMnO4 ñaë c
CH3 CH2 C CH3
O
Butanon
+
CH3COOH
10
6. Ñieàu cheá aceton
a.
CH3CH2OH CuO
CH3CH2OH
1) CH3MgI
CH3CHO
+
KMnO4/H
+
2) H2O/H
CH3COOH
CH3 CHOH CH3
Ca (OH) 2
(CH3COO) 2Ca
[O]
t0
CaCO3
CH3COCH3
CH3COCH3
b.
CH3CH2CH2OH
H2SO4ññ ,180 C
H2O
0
CH3 CH CH2
H2O
CH3 CHOH CH3
[O]
CH3COCH3
c.
CH CH
CH CH
Na
H2O
HgSO4/H2SO4
CH C Na
CH3CHO
CH3I
CH C CH3
1) CH3MgI
+
2) H2O/H
+
H2O/H
CH3 CHOH CH3
CH3COCH3
[O]
CH3COCH3
11
7.
e.
2 CH3CHO
CH3 CH CH CHO 2 CH3CH2OH CH3 CH CH CH(OC2H5) 2
HO
H2O
H2/Ni
CH3CH2CH2CH(OC2H5) 2
H2O
CH3CH2CH2CHO
[O]
CH3 C CH 2 CH3
f.
g.
O
2 CH3CHO
CH 3CHO
HO
H2O
C2H5MgCl
CH3 CH CH CHO
CH 3 CH CH 2 CH 3
+
H2O/H
CH 3CHOHCH 2CH 3
OMgCl
[O]
h.
CH3 C CH 2 CH3
O
13
7.
i.
CH 3CHO
C2H5MgCl
CH 3 CH CH 2 CH 3
+
H2O/H
CH 3CHOHCH 2CH 3
OMgCl
H2SO4ññ ,1800C
H2O
CH 3 CH CH CH 3
Br2
CH 3 CH CH CH 3
Br Br
2 NaNH2/NH3
k.
KMnO4
CH3CHO
H2/Ni
CH3COOH
C2H5OH
CH2 CH CH CH 2
+
H
CH3COOC2H5
14
8. Hoaøn thaønh chuoãi pöù:
a.
C2H 5 CH CH 2 CH 2 Br KOH/alcol
C2H 5 CH CH CH 2
CH 3
C2H 5 CH CH CH 3
CH 3
CH 3 Cl
3-methyl-1-penten
NaOH dd
HCl
C2H 5 CH CH CH 3
CH 3 OH
3-methyl-2-pentanol
[O]
2cloro-3-methyl-1-penten
C2H 5 CH C CH 3
CH 3 O
3-methyl-2-penanon
C6H5NHNH2
C2H 5 CH C CH 3
CH 3 NNHC6H 5
3-methyl-2-pentanonphenylhydrazon
15
8.
b.
(CH3) 2CH C CH3
[H]
(CH3) 2CH CH CH3
O
Mg/ether khan
HBr
(CH3) 2CH CH CH3
OH
(CH 3) 2CH CH CH3
Br
HCHO
(CH 3) 2CH CH CH3
MgBr
2-magnebromid-3-methylbutan
+
H2O/H
CH2OMgBr
2,3-dimethyl-1-oxymagnebromidbutan
(CH3) 2CH CH CH3
CH2OH
2,3-dimethyl-1butanol
16
8
c.
Br2
CH3 CH 2 CH CH 2
CH3 CH2 CH CH2 2KOH/alcol
Br
NaNH2/NH3
CH3 CH 2 C CH
Br
CH 3 CH 2 C C Na
CH3I
CH 3 CH 2 C C CH 3
natributynylid
H2O
++
+
Hg /H
d.
O C6H5NH2
CH 3 CH 2 CH C CH 3
CH 3 CH 2 CH 2 C CH 3
OH
O
N C6H5 LiAlH4
ClCH2CH2CH2N (C2H5) 2
NaNH2
NH C6H5
N CH2CH2CH2 N (C2H5) 2
C6H5
17
8.
e.
Cl CH2 C O
CH 3
1)
C2H5MgBr
+
2) H2O/H
C 2H 5
Cl CH 2 C OH
C6H5COCl
C 2H 5
Cl CH2 C O C C6H 5
CH 3
CH 3
O
1-cloromethyl-1-methylpropylbenzoat
HN(CH3)2
CH3
CH3
C2H5
N CH2 C O C C6H5
CH3
O
1-N,N-dimethylaminomethyl-1-methylpropylbenzoat
18
9. Phaõn bieọt:
a.
Haloform
CH3 C CH3
+ I2
+
KOH
CHI3 + CH3COOK
+
KI
+
H2O
O
CH3CH2CHO
b.
khoõng coự pửự haloform
CH3 C H
O
CH3CH2CHO
Haloform
CHI3
khoõng coự pửự haloform
19
9.
c.
2,4-dinitrophenylhydrazin
NO2
CH3
CH3
O2N
C O
NHNH2
CH3
CH3
CH3
CH3
CH OH
Isopropanol
Lucas
HCl / ZnCl2
t
o
NO2
C N NH
CH3
CH3
tuûa vaøng
NO2
+
H2O
CH Cl
tuûa traéng
20
9.
d.
Cl
CH3 C C3H7
H2O/HO
CH3 C C3H7
Cl
cho pöù haloform
O
2,2-dicloropentan
Cl
C 2H 5 C C 2H 5
Cl
H2O/HO
C 2H 5 C C 2H 5
khoân g cho pöù haloform
O
3,3-dicloropentan
21
10.
Ñieàu cheá pentaerythritol. Goïi teân theo IUPAC
CH 3 CHO
H CHO
HO
CH 2 CHO 2 H CHO
CH 2OH
HO
CH 2OH
HOCH 2 C CHO
CH 2OH
H CHO/ HO
CH 2OH
HOCH2 C CH 2OH
+
HCOO
CH 2OH
2,2-di(hydroxymethyl)propan-1,3-diol
22
ALDEHYD VAØ CETON THÔM
23
1. Goïi teân:
CHO
Cl
CHO
CHO
SO 3H
NO 2
2-cloro-4-nitrobenzaldehyd
m-formylbenzensulfonic
m-sulfobenzaldehyd
OCH3
OH
3-methoxy-4-hydroxybenzaldehyd
vanilin
CH CH CHO
CH3
-(p-tolyl) acrolein
3-(p-tolyl) propenal
p-methylcinamaldehyd
COCH 3
methylphenylceton
acetophenon
COCH CH 2
phenylvinylceton
24
CH 3
Ethyl-p-methoxyphenylceton
C
CH 3
CH 3 C N OH
acetophenoxim
O
Di(p-tolyl) ceton
methylphenylcetoxim
p,p'-dimethylbenzophenon
CHO
(H3C)2N
C
N(CH3)2
O
di-(p-dimethylaminophenyl) ceton
CHO
9,10-formylanthracen
anthracen-9,10-dicarbaldehyd
O
O
anthraquinon
anthracen-9,10-dion
2-formylthiophen
S
CHO
thiophen-2-carbaldehyd
25
