B gio dc v o to

k thi chn hc sinh gii quc gia

lp 12 THPT nm 2005

thi chnh thc

Mn: ho hc, Bng A

Thi gian: 180 pht (khng k thi gian giao
)
Ngy thi th hai: 11/3/2005

Cu 1
1. Vit s iu ch cc axit sau y:
a) Axit: benzoic, phenyletanoic, 3-phenylpropanoic t benzen v cc
ho cht cn thit khc.
b)
Axit:
xiclohexyletanoic,
1-metylxiclohexan-cacboxylic
t
metylenxiclohexan v cc ho cht cn thit khc.
2. Sp xp (c gii thch) theo trnh t tng dn tnh axit ca cc
cht trong tng dy sau:
a)
Axit:
benzoic,
phenyletanoic,
3-phenylpropanoic,
xiclohexyletanoic,
b1-metylxiclohexan-cacboxylic.
)
COOH

COOH

(A)

CH2COOH

COOH

(D)

(C)

(B)

3. a) Sp xp (c gii thch) theo trnh t tng dn nhit

nng chy ca cc cht sau:
COOH
;

COOH

COOH

(A)

(C)

(B)

b) Sp xp (c gii thch) theo trnh t tng dn nhit si ca

cc cht sau:
N

;
N

(A)

S
(B)

N
H (C)

H (D)

;
(E)

Cu 2
L-Prolin hay axit (S)-piroliin-2-cacboxylic c pK1 = 1,99 v
pK2 = 10,60. Piroliin (C4H9N) l amin vng no nm cnh.
1. Vit cng thc Fis v cng thc phi cnh ca L-prolin. Tnh pH I
ca hp cht ny.
2. Tnh gn ng t l dng proton ho H 2A+ v dng trung ho HA
ca prolin
pH = 2,50.

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3. Tnh gn ng t l dng eproton ho A v dng trung ho

HA ca prolin
pH = 9,70.
4. T metylamin v cc ho cht cn thit khc (benzen, etyl acrilat,
natri etylat v cc cht v c), hy vit s iu ch N-metyl-4phenylpiperiin.
Cu 3
Hp cht hu c A cha 79,59 % C; 12,25 % H; cn li l O
ch chim mt nguyn t trong phn t. Ozon phn A thu c
HOCH2CH=O ; CH3[CH2]2COCH3 v CH3CH2CO[CH2]2CH=0. Nu cho A
tc dng vi brom theo t l mol 1:1 ri mi ozon phn sn phm
chnh sinh ra th ch thu c hai sn phm hu c, trong s
c mt xeton. un nng A vi dung dch axit d dng thu c sn
phm B c cng cng thc phn t nh A, song khi ozon phn B ch
cho mt sn phm hu c duy nht.
1. Xc nh cng thc cu to v gi tn A.
2. Tm cng thc cu to ca B v vit c ch phn ng chuyn
ho A thnh B.
Cu 4
1. D-Galactoz l ng phn cu hnh v tr s 4 ca Dglucoz. Trong dung dch nc D-galactoz tn ti 5 dng cu trc
khc nhau trong mt h cn bng. Hy dng cng thc cu hnh
biu din h cn bng v cho bit dng no chim t l cao
nht.
2. D-Galactoz l sn phm duy nht sinh ra khi thu phn hp
cht A (C12H22O11). thc hin phn ng ny ch c th dng cht
xc tc l axit hoc enzim -galactoziaza. A khng kh
c dung dch Fehling, song tc dng c vi CH3I trong mi trng
baz cho sn phm ri em thu phn th ch thu c 2,3,4,6tetrao
O OH
3. un nng D-galactoz
165cu
C sinh
ra mt
-O-metyl-D-galactoz.
Hy ti
tm
trc ca
A, vit cng thc
vng
hn
hp
sn
phm,
trong

c
mt
l
ng
nh
O
phng v cng thc cu dng ca n.
hp cht B. Cho B tc dng vi CH3I (c baz xc
tc) ri thu phn sn phm sinh ra th thu
HO
B
c hp cht C l mt dn xut tri-O-metyl ca DOH
galactoz. Hy gii thch qu trnh hnh
thnh B v vit cng thc Fis ca C.
Cu 5
2-(1-Hiroxipentyl)xiclopentanon (A) l cht trung gian trong
qu trnh tng hp mt cht dng lm hng liu l metyl (3-oxo-2pentylxiclopentyl)axetat (B).

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1. Vit cng thc cu to ca A v s cc phn ng tng hp A

t axit aipic (hay axit hexanioic) vi cc cht khng vng v cc
cht v c khc.
2. Vit cng thc cu to ca B v s cc phn ng tng hp B
t A v cc ho cht cn thit khc.
3. B c tt c bao nhiu ng phn cu hnh? Hy vit cng thc
lp th ca ng phn c cu hnh ton l R.

Th sinh khng c s dng ti liu ngoi qui

nh.

Gim th khng gii thch g thm.

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