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CHUYN CACBOHIRAT
A. i cng v danh php
Cu 1. Gi tn cc monosaccarit sau:
a. HOCH2CHOHCOCH2OH
b. HOCH2(CHOH)4CHO
c. HOCH2(CHOH)4CH2CHO
Cu 2. Gi tn cc monosaccarit sau:

Cu 3. Cho nhng tinh th D glucoz c im nng chy 1460C ha tan vo nc cho nng sut quay cc ban
u l +1120C, nhng sau gim xung ti 52,70C. Mt khc, khi cho nhng tinh th D glucoz c im chy
1500C ha tan vo nc cho nng sut quay cc ban u l +190C, nhng dn dn tng ln n 52,70C. l s
quay h bin gia hai ng phn anome v . Hy tnh thnh phn phn trm hai ng phn trong dung dch .
Bit rng hm lng cc dng ng phn mch h l khng ng k.
B. Ha hc lp th
Cu 4. Vit cng thc cu trc cho mi hp cht sau:

a. Cng thc chiu Fischer v Haworth ca

;
b. Cu dng thch hp ca D mannoz.
c. Cu dng thch hp ca L arabinoz (dng v )
d. Cng thc Haworth cho -D-glucopyranoz. Cng thc ca dng c khc im no?
e. Cu dng gh cho -D-glucopyranoz
f. Cu dng gh bn v km bn cho -D-idopyranoz (ng phn epime ca D-glucoz).
g. Trong fructoz nguyn t cacbon no l C-anome? Vit cng thc chiu Fischer cho cc ng phn anome ca
D-fructofuranoz v D-fructopyranoz.
h. Cng thc chiu Haworth cho cc ng phn anome ca D-fructofuranoz v D fructopyranoz?
Cu 5. Ch r cu hnh D/L cho cc cng thc chiu Fischer di y ca glixerandehit.
OH
(b) HOH2C

CHO

CHO

(c)

CH2OH
OH

Cu 6. Cho bit s khc nhau gia D-erythroz v D-threoz khi chng b oxi ha nh nhng v b kh
C. Phn ng
Cu 7. a. Cho bit cc sn phm to thnh khi cho HIO4 tc dng vi (i) HOCH2-CHOH-CHOH-CHOH-CHOHCHO (andoz) v (ii) HOCH2-CHOH-CHOH-CHOH-CO-CH2OH (2-xetoz).
b. Da trn loi phn ng ny trnh by mt phng php n gin phn bit hai ng phn ny.
Cu 8. a. Cho bit cc cht trung gian v sn phm to thnh khi cho D-threo tc dng vi PhNHNH2.
b. Khi D-erythro tham gia phn ng ny th sn phm l g? Gii thch sn phm thu c.
c. C th kt lun iu g khi tin hnh phn ng ny vi cc ng phn epime.
Cu 9. a. Vit hai sn phm l ng phn hnh thnh trong phn ng gia D-threo v NaCN/HCN.
b. Kt qu ca phn ng ny c nh hng g n mch cacbon?
Cu 10. Cho bit s bin i cu trc ca (a) glucoz v (b) fructoz khi phn ng lin tc vi (1) NaCN/HCN,
(2) H3O+, (3) HI/P.
Cu 11. a. Cho bit cu to cc cht trong s chuyn ha di y, trong B l sn phm tch ra t cn bng
thun nghch vi A:
H
Br2 / H 2O
pyridin
Na / Hg
A
D
Andoz
B
C
b. Cu trc mch thay i nh th no sau cc bc chuyn ha ny?
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Cu 12. a. Cho bit cu to cc cht trong s chuyn ha di y:

CaCO3
Br2 / H 2O
H 2O2 / Fe ( III )
Andohexoz
E
F
G
b. Cu trc mch thay i nh th no?
c. Cho kt lun v kh nng hnh thnh ng phn epime?
Cu 13. a. Cho bit cu to cc cht trong s chuyn ha di y:
NH 2OH / baz
Ac2O / NaOAc
MaOMe / MeOH
Andohexoz
H
K
J
b. Cu trc mch thay i nh th no?
c. Cho kt lun v kh nng hnh thnh ng phn epime?
Cu 14. Hon thnh cc s bin ha sau:
a.

1.CH3OH
HCl long
NH2OH
C

A
B
2.KOH

b.

CH3OH
(CH3 )2 SO4

E
F
HCl khan
NaOH

H 2O,H
C2H5OH

M
N
Na

c.

Cu 15. Dng cng thc Fischer hon thnh s chui phn ng theo phng php ging v Wohl:
AcO

Ac O d

2
2
D glucoz
oxim (A)
C16H21O10N (C)
C5H10O5 (D)
C18H25O12N (B)
AcOH
NaOH
Gii thch s to thnh D t C.
D. Xc nh cu trc monosaccarit
Cu 16. Tin hnh thoi phn Ruff mt andohexoz hai ln to ra mt andotetroz, oxi ha andotetroz bng
HNO3 to thnh axit meso-tartaric. Andohexoz ban u thuc dy D hay L?
Cu 17. D-andohexoz no khi b oxi ha bi HNO3 to ra axit meso andaric?
Cu 18. Tin hnh mt ln thoi phn Ruff vi D- alloz v D-galactoz sau oxi ha bng HNO3 to ra tng
ng mt ng phn meso v mt ng phn hot ng quang hc ca axit pentaandaric. Kt qa ny c ph hp
vi kt qu tm c cu 17 hay khng? C cc D-andohexoz no khc to c mt ng phn hot ng
quang hc hoc mt ng phn mezo ca axit pentaandaric khi chng chng cng tri qua cc giai on phn ng
nh trn?
Cu 19. Mi mt andohexoz nh D-alloz, D-glucoz v D-taloz u to c axit meso-heptandaric sau khi
oxi ha mt trong hai sn phm ca phn ng tng mch Kiliani. Xc nh cu to ca andohexoz v axit meso,
bit taloz l ng phn C2-epime ca galactoz.
Cu 20. Xc nh cu to ca D-arabinoz, bit andoz ny thu c t phn ng thoi phn Ruff ca D-mannoz
(mt ng phn C2-epime ca glucoz).
Cu 21. Vit cu to ca D-riboz, mt cu t ca ARN, bit rng D-riboz v D-arabinoz to osazon ging nhau.
Cu 22. Cc andopentoz l D-xyloz v D-lyxoz to osazon ging nhau v khi b oxi ha th tng ng to mt
ng phn mezo v mt ng phn hot ng quang hc ca axit andaric. Vit cng thc cu to ca chng.
Cu 23. Vit cng thc cu to cho hai vng lacton su cnh hnh thnh t axit glucaric (axit andaric ca glucoz).
Kh cc lacton trn to thnh axit andonic, lacton ca axit ny c x l vi Na/Hg v CO2 to thnh
andohexoz. Vit cu to ca mi andohexoz to thnh v cho bit cu hnh ca chng thuc dy D hay L.
Cu 24. Ti sao cc andoz phn ng c vi dung dch Fehling v PhNHNH2 nhng li khng phn ng vi NaHSO3.
Cu 25. a. Vit hai sn phm ca phn ng gia mt andohexoz vi lng d Ac2O/NaOAc.
b. Nhng sn phm ny c phn ng vi dung dch Fehling hoc PhNHNH2 hay khng? Gii thch.

NH OH

MeONa

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GV: NGUYN THU HIN - 0975657445

Cu 26. Vit hai sn phm ca phn ng gia mt andohexoz vi lng d (MeO)2SO2 hoc MeI trong dung
dch NaOH v gii thch s hnh thnh cc sn phm ny?
Cu 27. Tnh thnh phn % cc anome thu c ti cn bng hnh thnh do s nghch chuyn ca glucoz, bit gi
tr gc quay cc ring ca v -D-glucoz ln lt bng +112o, +19o v gi tr gc quay cc ca hn hp ti cn
bng l +52,7o.
Cu 28. T cc d kin sau cho bit D-glucoz l furanoz hay pyranoz? Gi tn cc sn phm trung gian ca
qu trnh ny :
HNO3
Me2 SO4 / NaOH
MeOH / HCl
ddHCl
D-glucoz
A
B
C
axit 2,3-dimetoxisucxinic + axit 2,3,4-trimetoxiglutaric.
Cu 29. T dy chuyn ha di y, lm th no xc nh mt metyl glucosit c vng pyranoz hay furanoz:
3. H 3O
1. HIO4
2.dung dch Br2

ng

Cu 30. Cht ng A c cu trc phn t C6H12O6. A l i tng tng hp theo phn ng Killiani thu c
hai heptoz c cng thc C7H14O7 l B v C. D glucoz cng thc hin cc phn ng nh qu trnh tng hp trn
v cng thu c hai heptoz khc nhau l D v E. B v D b oxi ha vi axit HNO 3 cho cng mt axit khng hot
ng quang hc c cng thc C7H12O9. Vit cng thc cc cht ng t A n E.
E. Disaccarit v Polisaccarit
Cu 31. Mantoz phn ng nh th no vi (a) dung dch Fehling, (b) dung dch NaOH, (c) dung dch brom, (d)
lng d PhNHNH2, (e) dung dch HCl, (f) enzim mantaza v (g) enzim emulsin.
Cu 32. Khi oxi ha mantoz bng dung dch brom thu c axit cacboxilic (C), axit ny phn ng vi
(MeO)2SO2/NaOH to ra mt dn xut octametyl (D).Thy phn (D) trong HCl thu c 2,3,4,6-tetra-O-metyl-Dglucopyranoz (E) v axit 2,3,5,6-tetra-O-metyl-D-gluconic (F). S dng cc d liu trn v kt qu ca cu 31 lp
lun xc nh cu to mantoz v cc cht C, D, E, F.
Cu 33. (a) Lp lun xc nh cu to ca lactoz, mt disacacrit c trong sa, bit: (1) Thy phn trong emulsin
to ra D-glucoz v D-galactoz, (2) l mt ng kh c kh nng nghch chuyn. (3) Khi thy phn osazon
ca n thu c D-glucosazon v D-galactoz, (4) Oxi ha nh nhng, sau metyl ha ri cui cng thy phn
to cc sn phm tng t nh sn phm thu c t mantoz. (b) Vit cng thc cu to osazon ca lactoz.
Cu 34. M t qu trnh ri lon tiu ha gy ra do s d ng lactoz.
Cu 35. (a) Bng cch no chng ta bit rng mantoz, xenlobioz v lactoz khng cha cu t L-monosaccarit?
(b) Cc ng L c xut hin trong t nhin hay khng?
Cu 36. T cc d kin sau y hy xc nh cu trc ca saccaroz (mt loi ng n ph bin c tch t cy
ma v c ci ng): (i) n khng kh c thuc th Fehling v khng nghch chuyn. (ii) Khi thy phn bng
men mantaza hoc emulsin u to sn phm l D-glucoz v D-fructoz. (iii) Metyl ha sau thy phn to ra
2,3,4,6-tetra-O-metyl-D-glucopyranoz v tetrametyl D-fructoz. (b) Phn no ca cu trc khng cha c xc
nh ? (c) Gi tn saccaroz theo danh php IUPAC.
Cu 37. (a) nh ngha ng nghch chuyn. (b) Tnh gc quay cc ring ca ng nghch chuyn, bit rng Dglucoz c []D = 52,7o v D-fructoz c []D = -92,4o.
Cu 38. Cho bit sn phm to thnh khi thy phn saccaroz c metyl ha hon ton.
Cu 39. Lp lun xc nh cu trc ca mt disaccarit (A) c cng thc phn t C 10H18O9, bit rng khi oxi ha
bi brom, sau metyl ha v cui cng x l vi men mantaza th thu c sn phm l 2,3,4-tri-O-metyl-Dxyloz v axit 2,3-di-O-metyl-L-arabinoic.
Cu 40. Lp lun xc nh cu trc ca gentiobioz C12H22O11, bit rng gentiobioz c kh nng nghch chuyn
v khi thy phn bi men emulsin to D-glucoz. Thy phn sn phm metyl ha ca gentiobioz sinh ra 2,3,4,6tetra-O-metyl-D-glucopyranoz v 2,3,4-tri-O-metyl-D-glucopyranoz.
Cu 41. Lp lun xc nh cu trc ca (a) trehaloz khng kh C12H22O11, bit khi thy phn bng mantaza thu
c D-glucoz, (b) isotrehaloz c cu to tng t trehaloz, ch khc l c th thy phn bi mantaza hoc
emulsin. Thy phn c hai cht ny sau khi metyl ha u to sn phm duy nht 2,3,4,6-tetra-O-metyl-Dglucopyranoz.
Cu 42. Khi thy phn khng hon ton amyloz, mt thnh phn ca tinh bt c kh nng ha tan trong nc, to
ra mantoz v D-glucoz. Metyl ha, sau thy phn hon ton th sn phm chnh l 2,3,6-tri-O-metyl-Dglucopyranoz. Cho bit cu to ca amyloz.
Cu 43. Metyl ha sau thy phn amyloz thy c xut hin 2,3,4,6-tetra-O-metyl-D-glucopyranoz chim
hm lng t 0,2 n 0,4%. Gii thch ngun gc pht sinh sn phm ny.
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Cu 44. Khi metyl ha v thy phn amylopectin, mt thnh phn ca tinh bt c kh nng ha tan trong nc, to
sn phm chnh tng t amyloz. Tuy nhin cn c mt phn cc sn phm khc nh 2,3,4,6-tetra-O-metyl-Dglucopyranoz (chim hm lng khong 5%) v khong 5% 2,3-di-O-metyl-D-glucopyranoz. Lp lun xc nh
cu trc ca amylopectin.
Cu 45. (a) Cho bit mt phng php n gin nhn bit tinh bt. (b) Hin tng g xy ra khi tng nhit th
nghim nhn bit ny? (c) Cho bit s bin i cu trc tng ng vi cc hin tng thy c? (d) Hin tng
to ra t amyloz v amylopectin c ging nhau khng? Gii thch.
F. BI TP TNG HP
Cu 46. Mt isaccarit A khng c tnh kh. Khi thu phn trong mi trng axit, A cho sn phm duy nht l
pentoz B. Cng c th thu phn A nh enzim -glicoziaza song khng dng c -glicoziaza. T B c th
to ra D-glucoz bng cch cho tc dng vi HCN ri thu phn (xc tc axit) v kh.
a) Vit cng thc Fis v gi tn B theo danh php h thng.
b) Vit s cc phn ng chuyn ho B thnh D-glucoz.
c) Vit cng thc cu trc ca A dng vng 6 cnh phng.
d) khng nh cu trc vng 6 cnh ca A, ngi ta cho A tc dng vi CH3Br trong mi trng baz ri thu
phn (xc tc H+). Dng cng thc cu trc, vit s cc phn ng.
Cu 47. Monosaccarit A (t l glicoz A) c tn l (2S,3R,4S,5R)2,3,4,5,6pentahiroxihexanal. Khi un nng
ti 1000C, A b tch nc sinh ra sn phm B c tn l 1,6anhiroglicopiranoz. Dglucoz khng tham gia phn
ng ny. T A c th nhn c cc sn phm E (C5H10O5) v G (C5H8O7) theo s phn ng:

Br2
H2O

CaCO3

H2O2

HNO3

1. Vit cng thc Fis ca A v B.

2. A tn ti 4 dng gh (D-glicopiranoz). Vit cng thc ca cc dng v cho bit dng no bn hn c?
3. Dng cng thc cu dng biu din phn ng chuyn ho A thnh B. V sao
Dglucoz khng tham gia phn ng tch nc nh A?
4. Vit cng thc cu trc ca E v G. Hy cho bit chng c tnh quang hot hay khng?
Cu 48. Tm quy trnh tng hp vitamin C t D glucoz?
G. THI HC SINH GII
Cu 49. ( thi HSG quc gia, Vit Nam - 1998)
1. A l disaccarit kh c AgNO3 trong dung dch NH3, gm hai ng phn c kh nng lm quay mt phng
o
o
nh sng phn cc trong nhng iu kin thng nht biu th bng [] 25
D l + 92,6 v +34 . Dung dch ca mi
o
ng phn ny t bin i v [] 25
D cho cho ti khi cng t gi tr n nh l + 52 . Thy phn A (nh xc tc
axit) sinh ra B v C:
CHO
H
HO

OH

CHO
H

OH

HO

OH

HO

OH

CH2OH
(B)

OH
CH2OH
(C)

Cho A tc dng vi lng d CH3I trong mi trng baz thu c sn phm D khng c tnh kh. un nng D
vi dung dch axit long thu c dn xut 2,3,6-tri-O-metyl ca B v dn xut 2,3,4,6-tetra-O-metyl ca C.
(a) Vit cng thc cu trc (dng vng 6 cnh phng) cho B, C, A, D; bit trong phn t A c lin kt -1,4glucozit. Gii thch v vit cc phng trnh phn ng.
o
(b) V sao dung dch mi ng phn ca A t bin i v [] 25
D v cui cng u t gi tr 52 ? Tnh thnh phn
o
phn trm cc cht trong dung dch gi tr [] 25
D = 52 v vit cng thc cu trc cc cht thnh phn .
2. Metyl ha hon ton cc nhm OH ca 3,24 gam amilopectin bng cch cho tc dng vi CH3I trong mi
trng baz ri un thy phn hon ton (xc tc axit) th thu c 1,66.10-3 mol 2,3,4,6-tetra-O-metylglucoz v
1,66.10-3 mol 2,3-di-O-metylglucoz, phn cn li l 2,3,6-tri-O-metylglucoz.
(a) Vit cng thc cu trc (dng vng 6 cnh phng) ca 3 sn phm trn v cho bit xut x ca chng.
(b) Cho bit t l % cc gc glucoz ch c nhnh ca phn t amilopectin.

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(c) Tnh s mol 2,3,6-tri-O-metyl glucoz sinh ra trong th nghim trn.

Cu 50. ( thi HSG quc gia, Vit Nam - 1999)
T mt loi thc vt ngi ta tch ra c hp cht (A) c cng thc phn t C 18H32O16. Thy phn hon ton (A)
thu c glucoz (B), fructoz (C) v galactoz (D):
(a) Vit cng thc cu trc dng vng phng 5 v 6 cnh ca galactoz.
(b) Hidro ha glucoz, fructoz v galactoz thu c cc poliancol. Vit cng thc cu trc ca cc poliancol
tng ng vi (B), (C) v (D).
(c) Thy phn khng hon ton A nh enzim -galactoridaza (enzim xc tc cho phn ng thy phn ca galactozit) thu c galactoz v saccozoz. Metyl ha hon ton (A) nh hn hp CH3I v Ag2O, sau thy
phn sn phm metyl ha, thu c 2,3,4,6-tetra-O-metylgalactoz (E) v 2,3,4-tri-O-metylglucoz (G) v 1,3,4,6tetra-O-metylfructoz (H). Vit cng thc cu trc ca (E), (G), (H) v (A).
Cu 51. ( thi HSG quc gia, Vit Nam - 2000)
X l mt disaccarit khng kh c AgNO3 trong dung dch NH3. Khi thy phn X sinh ra sn phm duy nht l M
(D-andoz, c cng thc vng dng ). M ch khc D-riboz cu hnh nguyn t C2.
CH3OH / HCl
CH3 I / NaOH
H2O/ H
M

Q
dn xut 2, 3, 4 tri O metyl ca M.
a. Xc nh cng thc ca M, N, Q v X (dng vng phng).
b. Hy vit s cc phn ng xy ra.
Cu 52. ( thi HSG quc gia, Vit Nam - 2001)
Melexitoz (C18H36O16) l ng khng kh, c trong mt ong. Khi thy phn hon ton 1 mol melexitoz bng
axit s nhn c 2 mol D-glucoz v 1 mol D-fructoz. Khi thy phn khng hon ton s nhn c D-glucoz
v disaccarit turanoz. Khi thy phn nh enzim mantaza s to thnh D-glucoz v D-fructoz, cn khi thy phn
nh enzim khc s nhn c saccaroz. Metyl ha 1mol melexitoz ri thy phn s nhn c 1 mol 1,4,6-tri-Ometyl-D-fructoz v 2 mol 2,3,4,6-tetra-O-metyl-D-glucoz.
1. Hy vit cng thc cu trc ca melexitoz. Vit cng thc cu trc v gi tn h thng ca turanoz.
2. Hy ch ra rng vic khng hnh thnh fomandehit trong sn phm oxi ha bng HIO4 chng t c cu trc
furanoz hoc pyranoz i vi mt xch fructoz v pyranoz hoc heptanoz (vng 7 cnh) i vi mt xch
glucoz.
3. Cn bao nhiu mol HIO4 phn hy hai mt xch glucoz c cu trc heptanoz v s nhn c bao nhiu
mol axit fomic?
Cu 53. ( thi HSG quc gia, Vit Nam - 2002)
1. Oxi ho 150 mg amiloz bi NaIO4 thu c 0,0045 mmol axit fomic.
(a) Tnh s lng trung bnh cc gc glucoz trong phn t amiloz; bit rng khi oxi ho 1 mol amiloz bng
NaIO4, s gc glucoz u mch to ra 1 mol axit fomic, s gc glucoz cui mch to ra 2 mol axit fomic.
CHO
(b) Vit s cc phng trnh phn ng xy ra.
HO
2. Vit s cc phng trnh phn ng chuyn D-glucoz thnh L-guloz c cng thc bn. HO HH
Cu 54. ( thi HSG quc gia, Vit Nam - 1997)
H
OH
Mannoz (monosaccarit) HOCH2-CHOH)4-CH=O l ng phn ca glucoz. dng vng su HO H
cnh
CH
OH
2
mannoz ch khc glucoz ch nhm OH nguyn t C2 nm cng pha vi OH nguyn t
C3.
Oxi ha mannoz bng dung dch HNO3 100oC thu c sn phm Y cha 41,38%C, 3,45%H v 55,17%O. Y b
thy phn c trong mi trng axit cng nh baz to ra axit polihidroxidicacboxilic hoc mui tng ng. Xc
nh cng thc cu to ca Y, bit MY = 174vC.
Cu 55. ( thi HSG quc gia, Vit Nam - 2001)
1. Vit phng trnh phn ng iu ch D-fructoz t D-glucoz, bit rng D-glucozazon khi tc dng vi
benzandehit to thnh oson ca D-glucoz (HOCH2(CHOH)3COCHO).
2. Chitin (tch t v tm, cua...) c coi nh l dn xut ca xenluloz, trong cc nhm hidroxyl cc
nguyn t C2 c thay th bng cc nhm axetylamino (-NH-CO-CH3).
a) Vit cng thc cu to mt on mch ca phn t chitin.
b) Gi tn mt mt xch ca chitin.
c) Vit phng trnh phn ng xy ra khi un nng chitin vi dung dch HCl c (d), un nng chitin vi dung
dch NaOH c (d).
Cu 56. (Bi tp chun b IChO, Canada - 1997)
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D-andotetroz A khi phn ng vi axit nitric cho hp cht khng hot ng quang hc. Cng andotetroz ny khi
phn ng vi HCN, tip theo vi dung dch nc Ba(OH)2 cho hai axit andonic epime B v C. Cc axit andonic
ny nm trong cn bng vi cc -andolacton D v E tng ng ca chng. X l hn hp ny vi Na - Hg v
nc pH 3-5 thu c cc cht F v G tng ng. Oxi ha F bng axit nitric thu c axit andaric khng hot
ng quang hc H, trong khi thc hin phn ng ny vi E thu c axit andaric hot ng quang hc I.
Cho bit cu trc cc cht t A n I.
Cu 57. (Bi tp chun b IChO, Canada - 1997)
-D-(+) mannopiranoz l epime ca -D-(+) glucopiranoz
a. Hy vit cu trc dng gh bn vng nht ca n.
b. Cho bit sn phm phn ng ca - D - (+) mannopiranoz vi cc cht :
(a) Cu2+ + (m pH > 7)
(g) 5HIO4
(b) Br2, H2O (pH = 6)
(h) (CH3CO)2O d trong piridin
(c) HNO3
(i) 3 mol phenylhidrazin, H+
(d) CH3OH , HCl khan
(j) 1. Br2/H2O 2. Fe (III) sunfat , H2O2
(e) Sn phm (d) + (CH3)2SO4, NaOH
(k) 1. HCN 2. Ba(OH)2
+
(f) 1. NaBH4; 2.H2O; 3. H3O ; 4. Na-Hg, H2O, pH=3-5.
Cu 58. (Bi tp chun b IChO, Thi Lan - 1999)
1. Dng cng thc Haworth ngh mt hay nhiu cu to vng vi ha lp th c th c cho D-tagaloz.

(D)-tagaloz
2. Hai sn phm c cng thc C6H10O6 thu c khi D-arabinoz tc dng vi NaCN/H+ ri thy phn trong mi
trng axit. Vit cu to km theo ha lp th c th c ca hai hp cht v cho bit chng to thnh nh th no?
CHO
HO
H
1. NaCN/H +
H
OH
2. H3O+/ t o
H
OH
CH 2OH
(D)-arabinoz

?+?

Cu 59. (Bi tp chun b IChO, Canada - 1997)

Disaccarit A b thy phn bi axit long to hn hp gm D-glucoz v D-galactoz. Hp cht A l mt ng
kh v b oxi ha bi nc Br2 to axit B, axit ny c metyl ha bng (CH3)2SO4/NaOH to thnh hp cht octaO-metyl ha. Thy phn hp cht ny thu c axit tetra-O-metylgluconic C v tetra-O-metylgalactoz D. Hp
cht C b oxi ha bi axit nitric to thnh axit tetra-O-metylglucaric. Cht A b thy phn bi -galactosidaza tch
t hnh nhn. Cho bit cu trc ca A, B, C, D.
Cu 60. Phn ng oxiha ct mch gluxit bi HIO4 c nhiu mc ch khc nhau.
(cc nhm-CHOH- v -CHO H-COOH; -CH2OH H-CHO ; >C=O CO2)
a) D Arabinoz l ng phn cu hnh C2 ca D Riboz. xc nh cu to ca n ngi ta thc hin cc
phn ng sau:
O
HO

1) H3O
CH3OH
HIO4
HOOCCO
B
DArabinoz
A
2) Br2 / H 2O
HCl

b) Nu phng php phn bit D glucoz vi D fructoz

OH
HO

OH