DE KIEM TRA HC PHAN CHUYN DE HP CHT DJ VNG

HO 4C NM HC 20010-2011 THI GIAN 45 PHT

Cu 1. (2 dim)
Dng cng thuc cu tao, cu hnh d vit cc phuong trnh phan ung ha hoc sau :
1. A + H
2
O
NaOH
B + C
2. A + O
2
xt
C
3. B + CuO
o
t C
A + Cu + H
2
O
4. C
o
t C
D + CO
2

5. (2S,3R,4S)-2,3,4,5-Tetrahidroxipentanal
o
2 4
SO H
t C
A + H
2
O
6. A
o
350
CaO NaOH
C

D + CO
7. A + phenol
NaOH
E (polime c cu tao khng gian 3 chiu).
8. (2R,3S,4S,5R)-2,3,4,5,6-pentahidroxihexanal + HNO
3
X + NO
2
+ H
2
O
9. X + NH
3
(du) Y
10. Y
o
t C
Glixerin
Z + CO
2
+ NH
3
+ H
2
O.
11. D + NH
3
o
2 3
450
Al O
C
Z + H
2
O.
Cu 2. (1,5 dim)
Dng cng thuc cu tao, hon chinh phuong trnh tng hop 2,5-dimetylpirol v 2,5-
dimetylfuran theo phuong php Paal Knorr:
M + NH
3
o
t C
2,5-dimetylpirol + H
2
O
M
o
2 4
H SO , t C
2,5-dimetylfuran + H
2
O
Cu 3. (1 dim)
Dng cng thuc cu tao, vit cc phuong trnh tng hop 2-phenylindol tu phenyl hidrazin,
axetophenon v cc diu kin phan ung thch hop.
Cu 4. (1 dim)
Vit phuong trnh phan ung cua 2-metylindol khi dun nng voi metylvinylxeton tao ra 2-
metylcacbazol.
Cu 5. (1,5 dim)
D diu ch melamin (tn goi IUPAC l 1,3,5-triazin-2,4,6-triamin) trong cng cng
nghip, nguoi ta nung nng ure voi cc cht xc tc. Trng ngung melamin voi fomandehit
nguoi ta thu duoc nhua melamin-fomadehit. Dng cng thuc cu tao, hy vit cc phuong
trnh phan ung xay ra.
Cu 6 (1,5 dim)
Dng cng thuc cu tao d vit so d phan ung v goi tn cc cht trung gian:
Anilin
4
SO

o
2
H ac, 130 C
gl i xeri n/ni trobenzen
X
4 2 4
KMnO / H SO
Y
o
t C
Z
2
SOCl
T
3
NH
Nicotinamit.
Cu 7. (1,5 dim)
Tu 2-aminophenol, o-nitrophenol, glxerin, m-metoxiaxetophenon, clorofom, cc dung mi
cn thit, cc cht v co v cc diu kin phan ung cn thit c du, hy vit so d diu ch ra
hop cht: (E)-3-(8-hidroxiquinolin-5-yl)-1-(3-metoxiphenyl)prop-2-en-1-on.
H ET
Ghi ch : Sinh vin c s dng ti liu tham kho.
Dp n
Cu 1
O
CH=O
NaOH
O
CH
2
OH
O
COOH
+
O
CH=O
xt
O
COOH
+ O
2
1
2
O
CH
2
OH
t
o
C
O
CH=O
+ CuO + Cu + H
2
O
O
COOH
t
o
C
O
+ CO
2
H
CH=O
HO
OH H
H HO
CH
2
OH
t
o
C
O
CH=O
+ 3H
2
O
H
2
SO
4
2 + H
2
O
O
CH=O
t
o
C
O
+ CO
CaO-NaOH
(A) (B)
(C)
(A) (C)
(B)
(A)
(C)
(D)
(A)
(A) (D)
1)
2)
3)
4)
5)
6)
7)
O
CH=O
NaOH
(A)
OH
CH
CH
CH
O
O
O
n
+ 3H
2
O
(E)
OH
+
3n
n
H o }c :
Nha phenol f urf uranehi t
OH
OH
+ H
2
O
t
o
C
O
CH=O
+
O
O
O
O
O
O O O
OH
CH
OH
CH CH
CH CH
CH
OH
CH
OH
OH
CH CH
CH CH
CH
OH
O
O
CH
2
OH
OH H
H HO
OH
CH=O
H
HO H
(2R,3S,4S,5R)-2,3,4,5,6-
pentahi roxi hexanal
+ 6HNO
3
COOH
OH H
H HO
OH
COOH
H
HO H
+ 6NO
2
+ 4H
2
O
(X)
8)
9)
COOH
OH H
H HO
OH
COOH
H
HO H
+ 2NH
3
(X)
COONH
4
OH H
H HO
OH
COONH
4
H
HO H
(Y)
10)
COONH
4
OH H
H HO
OH
COONH
4
H
HO H
(Y)
t
o
C N
H
+ NH
3
+ 2CO
2
+ 4H
2
O
(Z)
11)
450
o
C
N
H
+ H
2
O
(Z)
O
+ NH
3
(D)
Al
2
O
3
Cu 2
CH
2
CH
2
C CH
3
O
C
O
CH
3
N
H
H
3
C
CH
3
+ NH
3
t
o
C
Hexan-2,5-i on 2,5-i metyl pi rol
+ 2H
2
O
CH
2
CH
2
C CH
3
O
C
O
CH
3
O
H
3
C
CH
3
t
o
C
Hexan-2,5-i on 2,5-i metyl furan
+ H
2
O
H
2
SO
4
Cu 3
NH-NH
2
+ O=C
CH
3
NH-NH=C
CH
3
+ H
2
O
Phenylhidrazin Axetophenon 1-phenyl -2-(1-phenyl etyl i en)hyrazi n
NH-NH=C
CH
3
N
H
+ NH
3
PPA
160
o
C
2-Phenyl i nol 1-phenyl -2-(1-phenyl etyl i en)hyrazi n
Cu 4
N
CH
3
H
N
H
CH
3
+ CH
2
=CH C CH
3
O
t
o
C
2-Metyl i nol Vi nyl metyl xeton 2-metyl cacbazol
Cu 5
O=C
NH
2
NH
2
N N
N NH
2
NH
2
H
2
N
6
t
o
C, xuc tac
+ 3CO
2
+ 6NH
3
Ure
Mel ami n
N N
N NH
2
NH
2
H
2
N
Mel ami n
t
o
C, xuc tac N N
N NH
NH
HN CH
2
CH
2
CH
2
+ 3nHCH=O n
n
+ 3nH
2
O
Mel ami n-f omandehi t
Cu 6
NH
2
C
3
H
5
(OH)
3
/C
6
H
5
NO
2
H
2
SO
4
, 130
o
C
N
KMnO
4
/H
2
SO
4
N
COOH
COOH
t
o
C
N
COOH
SOCl
2
N
COCl
NH
3
N
CONH
2
Ani l in Qui nol in Axi t pirii n-2,3
-icacboxyli c
Axit ni coti ni c Nictinoyl clorua Nicoti namit
(X)
(Y)
(Z) (T)
Cu 7
NH
2
OH C
3
H
5
(OH)
3
/o - HOC
6
H
4
NO
2
xt, t
o
C
N
OH
CHCl
3
/KOH
o - Ami nophenol
8-Hi roxi qui nol i n
N
OH
CH=O
5-Fomyl -8-hi roxi qui nol i n
Etanol , t
o
C
N
OH
C
H
C
H
O
OCH
3
HCl , t
o
C
C CH
3
O
CH
3
O
(E )-3-(8-Hi roxi qui nol i n-5-yl )-1-(3-metoxi phenyl )prop-2-en-1-on