Chinh phc nh cao Ha hc quc gia quc t Your dreams Our mission

S trang: 508. Kh A4

Gi ba: 179.000 vn

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Hy Lovebook bin c m ca em thnh hin thc
Hy c sch Lovebook chc chn c c 1 tm v vo i hc v cc trng chuyn ni ting
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Hy c sch Lovebook thng thc cc kinh nghim, kin thc ca cc th khoa, cc gio vin
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Hy c sch Lovebook c th xy dng nhng thi th THPT quc gia, bi kim tra cht lng.
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LOVEBOOK - Vn ti s hon ho
Danh mc sch v chnh sch khuyn mi: lovebook.vn - goo.gl/XeHwk5
Video bi ging: youtube.com/nhasachlovebook
Hotline bn hng: 0963 140 260 (Ms Nguyt), 0981 553 885 (Ms Hoi).
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 Ch k v li chc ca tc gi hoc thnh vin Lovebook

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Sch gc phi c ch k ca tc gi hoc ca thnh vin Lovebook. Bt k cun
sch no khng c ch k u l sch lu, khng phi do Lovebook pht hnh.
Li chc
& k tng

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 Chinh phc nh cao Ha quc gia quc t

i phi tri qua ging t nhng khng c ci

u trc ging t!
ng Thy Trm

Hy phn u vn ln khng ch bng khi c m

bng c con tim ca mnh na!
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Bn quyn thuc v Cng Ty C Phn Gio Dc Trc Tuyn Vit Nam VEDU Corp

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tin no m khng c s cho php trc bng vn bn ca cng ty.
 GIA NH LOVEBOOK

CHINH PHC NH CAO

HA QUC GIA QUC T

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a ch: 101 Nguyn Ngc Ni, Thanh Xun, H Ni

SCH LIN KT
CHINH PHC NH CAO HA QUC GIA QUC T

M s: 1L 173 H2015
In 2000 cun, kh 29,7 x 21cm ti CNG TY C PHN IN V TRUYN THNG KT THNH
a ch: S 81, t 6 Phng Ph Din, Qun Bc T Lim, H Ni
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Quyt nh xut bn s: 531 LK TN/ Q NXBHQGHN
In xong v np lu chuyn qu III nm 2015.
 LI NI U

L mt hc sinh chuyn, chc hn bn no cng m c c tham gia vo i tuyn Olympic

quc gia hoc quc t. Tuy nhin, vinh quang, nim t ho ny mi nm ch dnh cho mt vi thnh
vin xut sc ca mi tnh thnh.
c c v tr vinh d ny, cc em cn phi n lc c gng rt nhiu. Ngoi s h tr y tm
huyt ca thy c trong i, cc em cn phi t hc v nghin cu rt nhiu. i vi vic t hc, t
nghin cu th ti liu l mt yu t v cng quan trng. Hin nay ti liu ha hc sinh gii rt nhiu
nhng mt cun sch cha ng y ni dung n thi hc sinh gii hay Olympic th cha c. Vy nn
vic t hc ca cc em hc sinh cng nh vic ging dy ca cc thy c, c bit l thy c cc tnh
vng su, vng xa gp rt nhiu kh khn.
Nhn thc c iu ny, nhm i Tuyn Ha Quc T ca GSTT GROUP cng nhau bin
son nn cun CHINH PHC NH CAO HA HC QUC GIA QUC T. i Ha Quc T ca
chng ti bao gm:
Chu Vn Phng Thnh vin i quc Olympic Ha quc t 2013
Nguyn Vn Phng Huy chng Bc quc t 2012
H Quang Khi Huy chng Bc quc t 2013
Tin t Gii Nh quc gia nm 2013
Cun sch tng hp gn 500 bi tp ha hc c chn lc t rt nhiu ngun m i ng tc
gi tng tri qua. Khng ch chau chut tng bi tp a vo sch, chng ti cn a ra li gii rt
chi tit v c th cho tng bi tp. Mt s bi tp in hnh, chng ti cn a ra nhng li bnh lun,
nhng mo x l ngn gn.
Chnh v th, vi cun sch ny, cc bn hc sinh c th yn tm dnh trn thi gian khai thc
cun sch m khng phi phn tn thi gian i tm ti thm t liu trn mng hay nhng ngun khc
na. ng nh bn Nguyn Vn Phng ni: Ni dung cun sch l qu cho cc em chinh phc
gii quc gia hay thm ch l vng 2 chn i tuyn quc t.
Mc d rt c gng trau chut tng ni dung nhng do y l ln u tin bin son sch nn
chng ti khng th trnh khi nhng thiu st. Vy nn chng ti s rt bit n nu nhn c nhng
li gp t cc bn c gi.
Mi kin ng gp ca cc bn, cc thy c xin vui lng gi v a ch
o Hm th in t t trng t Ha hc Vedu: gopy.lovebook.vn@gmail.com
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Mt ln na, i ng tc gi xin chn thnh cm n!!!
Nhm bin son
Xin chn thnh cm n!
 MC LC

PHN I: PHN HU C...................................................................... .. 9

CNG THC CC TC NHN THNG GP................ ................... 10

CHUYN 1: XC NH CU TO CHT....................................... ........................................12

CHUYN 2: C CH PHN NG.............................. .............................................. 33

CHUYN 3:TNG HP HU C................................................... .................. 57

CHUYN 4: DY TNG HP HU C........................................................ ..... 74

CHUYN 5: HA HC CC HP CHT THIN NHIN.............. .......................... 133

CHUYN 6: GLUXIT V PROTEIN........................................................... ................ 201

PHN II: HA V C..................................................... ................................... 341

CHUYN 1: HT NHN - PHN NG HT NHN...................... ...... 219

CHUYN 2. LIN KT HA HC............................................ .................. 237

CHUYN 3: CU TRC TINH TH................................................. .......................... 248

CHUYN 4. NHIT NG LC HC......................................................... .............. 254

CHUYN 5. NG HA HC..................................................... ........................... 276

CHUYN 6: CN BNG TRONG DUNG DCH S IN LY IN HA HC. ........ 294

CHUYN 7. HA V C............................................................................. .... 341

B KIM TRA............................................................................................................... 370

PH LC : THI OLYMPIC HA QUC T NM 2014 V 2015............................................ 409

Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission

PHN HU C
Nh cc bn bit, phn hu c trong thi HSG Quc gia hay vng 2 u chim t l rt cao
(40%), v thng quyt nh rt nhiu n kt qu thi ca cc bn. Vy nn, lm sao hc hu c
mt cch hiu qu nht, cc ti liu, cc phn sp xp nh th no cc bn c th ghi nh mt cch
khoa hc nht. V iu quan trng l hc nh th no tip thu tt nht kin thc c v p dng
vo bi thi cho hiu qu v thng i thi gp c dng lm l rt kh ri, ch ng ni l lm ri.
Gia nh Lovebook chng ti xin gii thiu cc chuyn hu c c bin son bi 2 bn: Chu Vn
Phng - Cu hc sinh trng THPT Chuyn Vnh Phc; Tin t - Cu hc sinh trng THPT
Chuyn Bc Giang. Theo nh cc sch hu c truyn thng u chia hu c thnh cc phn da cc
nhm chc, nhng theo chng ti, vic chia nh vy s gip chng ta hc chuyn su v mt phn
nhng mt khc li hn ch kh nng mc ni vi nhau gia cc nhm chc nn chng ti mnh dn
chia phn hu c ny thnh cc chuyn nh cc phn trong mt thi cc bn c th t duy tru
tng hn v khng b ng khi vo phng thi:
- Xc nh cu to cht.
- C ch phn ng.
- Tng hp hu c.
- Dy phn ng ha hc.
- Ha hc cc hp cht thin nhin (quan trng).
- Gluxit, protein v cc bi tp l thuyt.
Cc bi tp cc phn c chng ti tng hp t cc ngun, cc din n Ha hc, t kinh nghim
chng ti c c trong 2 nm hc Quc gia. y l ln xut bn u tay nn cn nhiu thiu st, rt
mong c s gp ca cc bn chng ta c th ci thin kin thc ca chnh mnh.

XIN CM N

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Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission
CNG THC CC TC NHN THNG GP

BNG VIT TT V CNG DNG

Vit tt Tn Cng thc Tc dng

cu to
AIBN -Cht khi mo to gc t do.
BBN -Phn ng vi ni i, sau oxy ha bng
H2O2/OH- to nhm OH ngc quy tc
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Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission
Macopnhicop, ch p t l 1:1.
DBN -l base, xc tc cho cc phn ng cn xy ra
trong mi trng kim hoc sinh ra acid.
DBU -Tng t DBN.
DCC -xc tc cho p gia acid v amin to amide.
DMF -tc nhn formyl ha.
DIBAL -tc nhn kh nhng hot tnh yu hn LiAlH4.
DMSO -thng l dung mi, nhng cng dng lm cht
oxy ha.
DDQ -Cht oxy ha nh.
Grubbs -xc tc cho phn ng hon i anken.
LDA -l base mnh, xc tc cho cc phn ng cn to
anion.
PCC -Cht oxy ha, thng dng oxy ha nhm
OH thnh =O.
DHP -Cht bo v nhm OH trong tng hp hu
c(khng p vi amin).
NBS -Cht to gc Br, phn ng thng v tr
anlyl.
m- -tc nhn ca phn ng chuyn anken thnh
CPBA epoxit.
Sia2BH -ging BBN.
Ac- Acetyl CH3-CO- -AcCl, Ac2O: bo v nhm amin, to este.
Bn- Benzyl Ph-CH2- -nhm Bn d b loi b bng cch H2/Pd.
Bz- Benzoyl Ph-CO- -BzCl: bo v nhm amin trong tng hp hu
c.
-loi b bng CF3COOH/AcOH.
Cbz- Benzyloxycacbonyl BnOOC- -Ging Bz.Loi b bng H2/Pd.
TFA Trifloroacetic acid CF3COOH -axit mnh, dng loi nhm bo v.
TFAA Trifloroacetic anhydrit (CF3CO)2O -bo v nhm OH nhng t dng.
THF Tetrahydrofuran (CH2)4O -dung mi khng cc.
TMS Trimethylsilyl Me3Si- -bo v cc nhm c hydro lonh ng nh
ankin, ancolLoi b bng NH4F.
Ts p-Toluensulfonyl p-Me-C6H4- -TsCl: ch phn ng vi nhm OH bc 1 do
SO2- hiu ng khng gian.
-TsOH: acid mnh.
PPA Polyphotphoric acid -xc tc cho phn ng tch nc, cc phn ng
xy ra trong mi trng acid.
Ms Methylsulfonyl Me-SO2- -MsCl:chuyn nhm OH sang nhm Oms d
tham gia SN hn.
Tf Triflometansulfonyl CF3-SO2- -ging Ms nhng phn ng mnh hn.
TBS Tertbutyldimetylsilyl Me2t-BuSi- -bo v nhm OH.

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TBDPS Tertbutyldiphenylsilyl Ph2t-BuSi- -ging TBS nhng kn chn khng gian hn.
TBAF Tetrabutylamoni florua Bu4NF -loi nhm cha Silic.
TBHP Tertbutylhydroperoxide t-BuOOH -to gc hoc l cht oxy ha.

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Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission
CHUYN 1: XC NH CU TO CHT

Nhng bi tp dng ny thng c dng: cc nh ha hc tm c mt cht mi v h th cc tnh cht ha

hc ca n da trn cc phn ng c trng, cc phn ng oxy ha kh, thy phn, ct mch ri hc bt ta
xc nh cu trc cht cha bit. Dng bi tp ny cc bn cn nm r mt vi phn ng c trng c th suy
lun ra cu to ca cht cha bit.

Cc phn ng c trng ca cc nhm chc trong xc nh cu to hp cht hu c

1.Alkan
- Phn ng t chy, phn ng th halogen.
2.Alken
- Phn ng cng vi HX, X2, H2O theo quy tc Macopnhicop theo t l 1:1.
- B oxy ha bi KMnO4 (long lnh), OsO4 to diol, KmnO4/H+ to acid v cetone, O3/Me2S to aldehyt v
cetone, O3/H2O2 to acid v cetone.
- Phn ng vi peoxit hay superoxit to epoxit.
- Tham gia phn ng Diels-Alder .
- Phn ng vi boran ri x l vi H2O2/NaOH to alcol ngc quy tc Macopnhicop.
- Kh bi H2/Ni, khng b kh bi NaBH4, LiAlH4
3.Alkin
- Phn ng cng vi HX, X2 theo t l 1:2.
- Cng H2O c xc tc Hg2+ to aldehit, cetone.
- B oxy ha bi KMnO4, ozon phn cho acid v cetone.
- Alkin u mch cho kt ta vi Ag+.
- Phn ng vi boran ri x l vi H2O2/NaOH cho aldehit hay ceton.
- Tham gia phn ng Diels-Alder .
- B kh bi H2/Pd-BaCO3 cho cis-alken, Na/NH3 cho trans alken, H2/Ni cho alkan.
- Alkin u mch c th phn ng vi Na/NH3 do nguyn t H linh ng
- C th ng phn alkin-1 thnh alkin -2 bng t-BuOK v alkin-2 thnh alkin-1 bng NaNH2.
4. Aren
- Tham gia SE, nhn benzen khng b oxy bi KMnO4, phn ng ozon phn.
- khi phn ng vi cht oxy ha th cc nhnh b oxy n acid carboxylic.
5. R-X
- c th phn ng SN1, SN2, E1, E2.
- Phn ng to cc hp cht c kim.
6. Alcol
- Phn ng vi Na, khng phn ng vi NaOH, khng lm si bt NaHCO3, khng lm i mu qu tm m.
- Tch nc to alken hay ete trong iu kin H2SO4.
- Th nhm OH bng cc nhm chc khc nh : -X, CN bng HX, PX3, PX5.
- Phn ng vi clorua acid, anhidrit acid, acid carboxylic to ester. Nhng thng thng alcol bc 3 khng tham
gia phn ng do b cn tr khng gian.
- Alcol bc 1, 2 b oxy ha bi PCC, PDC, CuO to aldehit, KMnO4/H+ to acid carboxylic.
- Diol-1,2 c kh nng to phc mu xanh tm vi Cu2+
- Cht c nhm CH(OH)-CH3 c kh nng tham gia phn ng halofom.
7. Phenol
- Phn ng vi Na, NaOH nhng khng lm si bt NaHCO3, khng lm i mu qu tm m.
- To phc mu tm vi FeCl3.
- Nhm OH khng tham gia SN nu khng c nhm ht e mnh nh vo nhn thm.
- D dng b oxy bi KMnO4 to quinon.
- Ngng t vi HCHO/kim.
8. Aldehit v cetone.
- Khng phn ng vi Na, khng lm si bt kh vi NaHCO3
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Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission
- Tham gia AN vo nhm C=O.
- Cng hp vi NaHSO3 to sn phm kt tinh.
- To cetal v acetal vi alcol trong mi trng acid.
- Cho phn ng vi thuc th Schiff cho mu hoc hng tm.
- Cho sn phm mu vng cam hoc kt ta vi 2,4-dinitrophenylhydrazin.
- Aldehit d dng b oxy ha thnh acid carboxylic.
- B kh bi nhiu cht kh cho alcol.
- Trong iu kin Zn(Hg)/HCl hay N2H4/KOH th b kh thnh alkan.
- Cht c nhm C(=O)-CH3 c kh nng tham gia phn ng halofom.
9. Acid carboxylic
- Lm qu tm, phn ng vi Na, NaOH, si bt kh vi NaHCO3.
- Phn ng vi SOCl2, PX5.
- Phn ng to ester, decarboxy.
- B kh bi LiAlH4, khng b kh bi NaBH4.
- -hydro acid khi un nng c th dime tch 2 phn t nc to lacton vng 6 cnh.
10. Ester
- B kh bi LiAlH4, khng b kh bi NaBH4.
- Tham gia SN.
11. Amin
- Lm xanh qu tm
- Amin mch h bc 1 phn ng vi HNO2 s to kh N2, amin thm s to mui diazoni bn 0-5oC.
- Amin bc 2 cho cht lng mu vng snh v khng tan trong nc.
- Amin bc 3 mch h khng phn ng , amin thm th xy ra SE v tr para.
- Amin bc 1 phn ng vi CHCl3/KOH to isonitril c mi c trng.

BI TP

Bi 1:Hp cht A (C11H17NO3) khng quang hot, khng tan trong mi trng trung tnh v kim
nhng d tan trong HCl long. A c hai nguyn t hidro linh ng, A phn ng vi Ac2O to B
(C13H19NO4) trung tnh. A phn ng vi MeI d sau thm AgOH, sn phm thu c C c cng
thc l C14H25NO4. un nng cht ny thu c Me3N v D (C11H14O3) trung tnh. D phn ng vi
O3 thu c HCHO v E. Andehit thm E phn ng vi HI to sn phm cha 3 nhm OH m
chng khng to c lin kt hidro ni phn t bn vng.
a) Xc nh cc cht cha bit.
b) T E v cc hp cht v c, hy iu ch A.
Bi 2:Hp cht A (C7H10O4) khng tc dng vi H2/Pd,to. A b thy phn trong mi trng axit ung
nng cho B (C4H8O2), A tc dng vi LiAlH4, sau thy phn trong mi trng H+ thu c C
(C5H10O3), C b oxy ha bi K2Cr2O7/H2SO4 thu c D (C5H6O5). Trong mi trng H+/to, D
chuyn thnh E (C3H6O), C tc dng vi H2/Ni cho F khng quang hot. Xc nh cng thc cu to
t A - F.
Bi 3: Mt hp cht trung tnh A c cng thc phn t C10H7NO2. Oxy ha mnh A thu c diaxit B
c cng thc phn t l C8H5NO6. Kh A thu c C c cng thc l C10H9N, hp cht ny khi oxy
ha thu c diaxit D c cng thc l C8H6O4. Hp cht A c th thu c bng cch nitro ha mt
hp cht thm. Xc nh cc cht cha bit.
Bi 4:R gng c bit n vi nhiu dc tnh v nhng tnh cht ca hng liu. Ti n rt
nhiu phng thuc c s dng gng nh mt v thuc tr cc bnh lin quan n ng rut, cm
lnh thng thng v mt s bnh khc. Mt vi hp cht c cho l gy ra v cay ca gng. Rt
nhiu trong s l nhng dn xut th n gin ca vng thm vi di mch khc nhau.

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Chinh phc nh cao ha quc gia quc t phin bn 2.0 Your dreams Our mission
Mt trong nhng n xut quan trng nht l Zingreon c cng thc phn t l C11H14O3. Hp
cht ny khng phn ng vi thuc th Tollens nhng c phn ng vi FeCl3 v 2,4-dinitrophenyl
hidrazin. Brom ha Zingreon bng dung dch brom th thu c duy nht mt dn xut monobrom.
Trong phn t Zingreon v sn phm kh ha theo Clemensen u to lin kt hidro phn t yu.
a. Xc nh cng thc cu to ca Zingreon t nhng d kin cho.
b. Zingreon c th c tng hp theo s sau:

Vit cng thc cu to ca A.

c. Zingreon c th chuyn ha d dng thnh Gingerol c cng thc phn t l C17H26O4, cng
l mt hp cht gy cay c tm thy trong r gng bng s sau:

Bi 5: Paracetamol l mt dc cht c cng dng gim au, h st c tng hp nhn to ln u

tin nm 1878 v c a vo iu tr nm 1948. Hin ti paracetamol tr thnh thuc gim au h
st thng dng nht hin nay vi nhiu tn bit dc c lu hnh. V n c rt t tc dng ph nn
c cung cp khng cn k n hu ht cc quc gia.
C mt chui phn ng c thc hin bt u t cht A (hnh di) nh sau: Khi cho cht A phn
ng vi O3 trong nc ta thu c 2 hp cht B v C. C 2 phn ng vi PBr5 thu c 2 cht tng
ng l D v E. D phn ng vi paracetamol thu c F v G. Cht E phn ng vi paracetamol cho H.
Hi F i qua AlCl3 khan thu c cht I. Trong s c mt ca HF/SbF5 th cht H ng phn ha
thnh J v K. Khi un nng cht I trong mi trng axit long thu c cht L. Trong cng iu kin
th J v K u cho M. Xc nh cng cu to cc cht cha bit.

Bi 6: Guaiol (C15H26O) l mt ancol rn trng thi tinh th c cu trc tecpen. Ancol ny c

phn lp t tinh du cy g Bulnesia, mt loi cy c th tm thy khu vc bin gii Argentina
Bolivia Paraguay. Khi dehidrat ha guaiol bng lu hunh th thu c mt hidrocacbon thm mu
xanh da tri khng cha vng benzen X (C15H18). Khi ha tan X vo trong H2SO4 c th mu xanh
bin mt. Cho nc vo dung dch ny th X c phc hi nguyn trng. Rt kh hidro ha guaiol
bng H2 xc tc. Qua mt lot cc chuyn ha di y, ta nhn c mt dn xut ca naphtalen A
(l sn phm duy nht).

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Xc nh cu trc ca guaiol v cht X nu bit rng trong phn t guaiol th nhm OH gn vo
nguyn t cacbon bc ba exocyclic ca h vng.
Bi 7: D tinh du c tc dng v li ch rt ln vi sc khe con ngi nhng khng phi l tt c
cc loi tinh du trn th gii c th s dng c, c mt loi tinh du c th gy c cho ngi s
dng. C Thuja l loi c thuc loi tng bch c tm thy nhiu Bc M v ng , tinh du ca
loi c ny c nhng nghin cu v khoa hc rt phc tp, n c th gy sy thai rt mnh cng l cht
c cho thn kinh.
Carvotanaxeton trong tinh du Thuja l mt terpin c cng thc phn t C10H16O khng phn ng
vi thuc th Tollens nhng lm mt mu nhanh dung dch KMnO4 long lnh, phn ng vi
hidroxylamin to ra sn phm kt tinh. Khi kh carvotanaxeton ngi ta thu c carvomenton
C10H18O v carvomentol C10H20O. Carvomenton phn ng vi hidroxylamin nhng khng lm mt
mu dung dch KMnO4 long lnh cn v carvomentol khng phn ng vi c dung dch KMnO4
long lnh ln hidroxylamin nhng li tc dng vi PCC. Trong mt bi th nghim oxy ha
carvotanaxeton vi hai nhm sinh vin ng thi thc hin trong c iu kin khc nhau th nhm th
nht thu c l axit 2,4-isopropylbutandioic v axit 2-oxopropanoic. Trong khi nhm hai thu c
3 isopropylpentandioic v axit axetic. Hy xc nh cu to ca carvotanaxeton , carvomenton,
carvomentol v vit s tng hp carvotanaxeton t limonen.

Bi 8: Ascaridol (A) l mt hp cht hu c trong t nhin c cu trc exotic. N c th tm c

trong phn hi ca tinh du cy goosefoot v nhiu cy khc. Ngi ta xc nhn cc thng tin sau:
A tinh khit ch c trong mi trng chn khng cao khi nng nhit n s pht n. Ph 13C NMR
ch ra trong A ch c mt lin kt i C=C. Dung dch cht A khng phn ng vi Na. Kh A bng
LiAlH4 cho cht B. Nu cht B phn ng vi NaBH4 trong s c mt AcOH, sau phn ng tip vi
H2O2 trong mi trng base th sn phm l hn hp hai ng phn cu trc. Phn ng ca B vi mt
ng lng H2/xc tc kim loi dn n s to thnh C. A phn ng vi hai ng lng H2/xc tc
kim loi dn n s to thnh C. C khng phn ng vi CrO3/axeton. S dehidrat ha C to thnh 2
ng lng nc v 2 hp cht hu c D v E. X l D bng O3 sau kh ha bng Zn/H2O dn
n s to thnh 1 ng lng glyoxal v 1 ng lng 6-metyl hepta-2,5-dion. Phn ng tng t
vi cht E to thnh 1 ng lng 3-oxo butanal v 1 ng lng 4-metyl-3-oxo pentanal. Cng c
thng bo xc nhn rng di nhng iu kin t nhin th A c to thnh khi chiu sng D v F c
mt xc tc clorophin. Xc nh cng thc cu to cc cht cha bit.
Bi 9: Hp cht D trong t nhin to ra nhiu dn xut a dng. Tinh du c gi tr cho tc ng chng
vim. D l mt hydrocarbon mu xanh, ha tan trong nc nhng khng mu trong axit mnh. Ti
trng thi lng cc, n c m men lng cc l 1,08 Debye, cao bt ng cho mt hydrocarbon. Cc
phn tch cho thy nc v carbon dioxid trong phn khi lng ca D l 1: 6,11.
a. Xc nh cng thc nghim ca D.
b. Cu trc chnh xc ca D c xc nh bng phng php c in:
Cho 2,4-dinitrochlorobenzene v pyridine phn ng vi nhau to cht A khng cha clo. A phn
ng vi 2 ng lng dimetylamin loi b 2,4-dinitroanilin, m vng to B. Tip B phn ng vi
cyclopentadiene trong s hin din ca natri methoxide. Trong iu kin , phn ng tch loi 1 phn
t dimetylamin thu c C (C12H15N). un nng C n 200oC th tch loi 1 phn t dimetylamin thu
c D. Hon thnh cu trc cc cht cha bit v gii thch cc mu sc ca D trong nc v axit
mnh.
c. Cht D c th thc hin rt nhiu phn ng khc nhau nh:
- Phn ng vi t-BuOH trong xc tc axit thu c F.
- D phn ng vi thuc th Grignard (phn ng cng) to thnh mt mui. Chuyn i bng nc
v qu trnh oxy ha vi tetrachloro p-benzoquinone dn n mt alkyl thay th ca hp cht D. Hai

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sn phm c th d on c. Mt trong s l G khi s dng MeLi, mt sn phm khc H (tn ti
2 ng phn) c th c to thnh khi s dng triphenylmetylliti. V cu trc ca F, G v H. Gii
thch s khc nhau gia s to thnh G v H.
d. Thm ch cc phc cht kim loi chuyn tip ca D cng c nhin cu. Nu cho D phn ng vi
LiAlH4 sau x l vi FeCl2 thu c hp cht I mu , l hn hp ca mt s lp th. Hydro ha
hn hp I thu c mt sn phm mu da cam J (C20H26Fe). Vit cng thc cu trc ca I v J.
Bi 10. Mt ankin D quang hot cha 89,52% C. Hp cht D c th b hidro ha/xc tc to n-
butylxiclohexan. X l D vi EtMgBr khng thy thot kh. Hidro ha D trn xc tc Pd/C tronng
quinolin (cht u c xc tc) v x l sn phm vi O3/H2O2 cho axit tricacboxylic quang hot E
(C8H12O6). Cht E khi un nng tch mt phn t nc v to F. Vit cng thc cu to cc cht cht
bit.
Bi 11. Cc nh khoa hc u nhng nm 1900 cho rng ch cn c h lin hp trong mt vng kn th
phn t c tnh thm. Xiclooctatetraen (A) lm sp nhn nh ny. N ln u tin c iu
ch bi nh ha hc ngi c Richard Willstater nm 1911.
a. V cng thc ca xiclooctatetraen, n c phng khng? Nu khng, hy v cc dng tn ti ca n.
b. Xiclooctatetraen tc dng vi 2 ng lng Kali to ra dianion. Vit cu to ca dianion ny v
cho bit tnh thm ca n? Dianion ny phn ng vi 2 mol axeton cho 2 sn phm C v D. Cho bit
cng thc cu to ca C v D.
c. Xiclooctatetraen phn ng vi m-CPBA to ra cht E, x l E vi axit Brontest thu c cht G
(C8H8O) c phn ng vi thuc th Tollens. Xc nh cng thc cu to cc cht cha bit.
d. Hon thnh dy phn ng sau bit K l cht trung gian.

Bi 12: Axit tropinic, C8H13O4N l mt sn phm phn hy ca atropin, mt ankaloid trong cy c c

dc. N khng phn ng vi benzensunfonyl clorua, KMnO4 long lnh hay Br2/CCl4. Axit tropinc
b metyl ha mnh theo s sau:

a. Xc nh cng thc ca axt tropinic.

b. Axit tropic c to thnh bng cch oxi ha tropinon vi CrO3.

Hy xc nh cu trc chnh xc ca axit tropinic.

c. Tropiliden, 1,3,5-xicloheptatrien, c iu ch t tropinon. Hy cho bit qu trnh xy ra nh
th no?
d. Khi kh ha bng tripinon to thnh tropin v pseudotropin c cng cng thc phn t C8H15ON.
Khi b un nng trong mi trng baz, tropin chuyn ha thnh pseudotropin. Hy cho bit cu trc
ca tropin v pseudotropin.

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Bi 13: Hai ng phn A v B c cng cng thc phn t l C9H11NO2. Chng u tan trong axit v
kim. Khi A v B ln lt tc dng vi NaNO2/HCl to thnh A v B tng ng c cng cng
thc phn t C9H10O3; ch B c tnh quang hot. Khi b un nng A v B vi H2SO4 c u to
thnh hp cht C c cng thc phn t l C9H8O2, khi oxi ha tip u to thnh axit terephtalic v
CO2. Xc nh cu trc ca A v B?
Bi 14: Kh naphtalen to thnh hp cht A. Ozon ha sn phm ny to thnh sn phm B c cng
thc C10H16O2, x l tip trong mi trng kim to thnh mt xeton C khng no C10H14O.
a. Xc nh cu trc cc sn phm.
b. Xeton trn c th chuyn ha thnh azulen, C10H8, mt hidrocacbon c mu xanh l cy. Nu cch
chuyn .Bi 15:Cho bit cu tr ca axit C27-phthienoic da vo d kin sau:

Metyl este ca V + 2C6H5MgBr, sau thy phn tao ra W (C36H58O).

Bit B l CH3(CH2)17COCH3.
Bi 16: Mt hp cht thm A(C6H9N), khng tan trong axit. A phn ang vi H2/Pd cho hp cht B
tan c trong axit. B phn ng vi mt ng lng CH3I cho C. C phn ng vi Ag2O khi ung
nng to thnh D(C7H15N). Metyl ha D sau nhit phn sn phm thu c 2-metylbuta-1,3-dien.
Xc nh A ,B ,C ,D.
Bi 17: Hp cht A(C9H8) lm mt mu dd Br2 trong CCl4. Khi hidro ha iu kin Ni,t0 to ra B
(C9H10) cn thm p sut to ra C (C9H16). Xc nh A, B, C. Oxi ha A thu c cht no?
Bi 18: 1,7-iclo-heptan-4-on trong mi trng baz to thnh sn phm c hai vng. X l sm phm
ny vi NH2OH trong mi trng axit to thnh A. Xc nh A?
Bi 19: Cho hp cht A c cng thc C10H10O, khng to mu vi FeCl3, to sn phm cng vi
NaHSO3. Cho A + I2/NaOH ( khng to kt ta), thn axit vo hn hp sau phn ng thu c hp
cht B c cng thc C10H10O2 khng lm mt mu KMnO4. B vi Br2/CCl4 vi s c mt ca HgO to
thnh C (1,2,3-tribrom-2-phenylpropan).
A tc dng vi NaBH4 to ra D, un nng D vi axit to ra E.
Xc nh A, B, C, D, E?
Bi 20: Hp cht thm A quang hot, cho phn ng vi Na kim loi nhng khng phn ng vi 2,4-
dintrophenylhidrazin. Khi x l A vi I2/NaOH thy xut hin kt ta vng.
Ozon phn A cho B(C9H10O) v C(C3H6O2). C B v C u cho kt ta vi 2,4-dintrophenylhidrazin.,
trong ch c C dng tnh vi thuc th Tollens. Trn l thuyt khi nitro ha B cho 2 sn phm l
D v E, thc t ch thu c D.
Axit ha sn phm nhn c khi th C bng thuc th Tollens thu c F(C6H8O4).
Xc nh nhng cht cha bit?
Bi 21: Cis-3,3-dimetyl-2-bromxiclohexan-1-ol + baz mnh to ra A ( ngng t vi NH2OH ).
Trans-3,3--dimetyl-2-bromxiclohexan-1-ol + baz mnh to ra B ( khng ngng t vi NH2OH ).
Xc nh cng thc A v B?
Bi 22: Hp cht A (-bisabolol) c tng hp trc tip t hp cht c magie G vi D.
T 4-metylpentan-1,4-diol to thnh hp cht ibrom A1. A1 tch HBr to thnh A2, A3, A4, vi A4 l
sn phm chnh. A4 tc dng vi Mg to ra G. D c to thnh t phn ng ca isopren vi metyl
vinyl xeton.
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Tm cc cng thc cu to trn?
Bi 23: Ozon phn A thu c B c cu trc nh sau:

Hidro ha A to ra hn hp X gm cc ng phn c cng thc C10H20.

a. Xc nh cng thc cu to ca A?
b. Vit cng thc cc ng phn cu to trong h hp X?
c. Vit cng thc lp th dng bn ca cc ng phn trong hn hp X?
Bi 24: Hp cht A (C5H11O2N) l mt cht quang hot. Kh A bng hidro c xc tc Ni s c B
(C5H13N) quang hot. Cho B tc dng vi HNO2 thu c hn hp gm ancol C quang hot v tert-
amylic.Xc nh cu to A, B, C.
Bi 25: Hp cht A (C5H9OBr) khi tc dng vi dung dch iod trong kim to kt ta vng. A tc
dng vi NaOH to ra 2 xeton B v C c cng cng thc phn t C5H8O. B v C u khng lm mt
mu dung dch thuc tm, lnh. Ch c B to kt ta vng vi dung dch iod trong kim. Cho B tc
dng vi CH3MgBr sau vi nc th c D. D tc dng vi HBr to ra hai ng phn E v F c
CTPT C6H11Br trong ch c E l mt mu dung dch thuc tm,lnh. Vit s phn ng t A to
thnh cc cht trn.

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P N CHUYN 1

Bi 1: E l andehit thm, E phn ng vi HI thu c sn phm c 3 nhm OH khng to lin kt

hidro ni phn t bn nn:

C nhit phn to D nn C c 2 cng thc l:

A khng quang hot nn C khng quang hot nn cng thc cu to ca C l 1.

vy A v B l :

S tng hp A t E.( coi E l R-CHO).

Bi 2: Ta c th thy hp cht A c = 3, A li khng phn ng vi H2/Pd nn A khng cha lin kt km

bn hoc vng km bn.
A b thy phn trong mi trng axit ung nng cho B (C4H8O2). B c = 1.
D (C5H6O5) trong mi trng acid/nhit chuyn thnh E (C3H6O). Tc l mt 2 nhm CO2. iu ny
chng t D l acid , ceton dicarbocylic.
A tc dng vi LiAlH4, sau thy phn trong mi trng H+ thu c C (C5H10O3), C b oxy ha
biK2Cr2O7/H2SO4 thu c D (C5H6O5), C tc dng vi H2/Ni cho F khng quang hot. iu ny chng t F
i xng.
Cng thc cu to cc cht t A n F.

Bi 3: Cht thm m nitro ha to ra A l naphtalen.

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Ch : cc nhm ht electron phn hot ha nhn thm nn khi khi tham gia phn ng oxy ha th
vng benzen no hot ha hn (mt electron cao hn) s b oxy ha. . iu ny c th d dng gii
thch v khi phn ng oxh- kh, cc cht oxy ha s nhn e, nn n s phn ng vi cht no c kh nng cho e
cao hn.

Bi 4: Cng thc cu to ca cc cht cha bit:

Bi ny a ra mt vn l Gingerol: c 2H c th tham gia phn ng. Nhiu sch vit rng trong mi
trng kim th kh nng enol s bn c t nhnh hn s cao hn( v d phn ng halofom), cn trong mi
trng acid th ngc li. Nhng trong nhiu phn ng th trong mi trng kim hay trong mi trng
acid,ceton u enol v pha c nhiu nhnh hn. Cc bn nn ch iu ny m chn hng phn ng chnh
xc nht.

Bi 5: Cng thc cu to cc cht t B n M:

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Bi ny thc cht l m t li mt dy phn ng. Cc phn ng trong bi ny u rt c bn, khng c phn ng

no kh v l c. Tuy nhin t cht D sang F v G. Nhiu bn s khng ngh ra c cht G v thng ngh rng
nu trong phn ng m xut hin t l 1:2 th phi cp nn thng cc bn khng vit. Cc bn ch D l
diclorua acid, v n c kh nng phn ng rt cao nn vic khng ch phn ng t l 1:1 rt kh khn.

Bi 6: X thm, X khng cha vng benzen, khi ha tan X vo trong H2SO4 c th mu xanh bin mt.
Cho nc vo dung dch ny th X c phc hi nguyn trng nn X c cha vng azulen.
Guaiol rt kh b hidro ha nn lin kt phi nm v tr cu.
Guaiol c nhm hidroxy cacbon exocyclic bc ba, chng t Guailol c cng thc :

Bi 7: Cng thc cu to cc cht cha bit:

Bi ny th cc bn da vo sn phm oxy ha, ri lp ghp cc mnh sn phm sao cho ph hp vi cng thc
cu to v phi tun theo quy tc isopren.

Sau y l s tng hp carvotanaxeton t limonen c dng trong cng nghip:

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- NOCl c dng phn ng vi ni i trong vng m khng nh hng n ni i ngoi vng.

- NOCl l NO+ v Cl-, tc y l phn ng AE bnh thng.
Ngoi ra khi cho oxim phn ng vi acid rt c th xy ra chuyn v nn trong cng nghip ta dng acid yu
trnh hin tng chuyn v.

Bi 8: Cng thc cu to cc cht t A n F:

Phn ng to cht A t cht F thc cht l phn ng Diels-Alder . cc bn ch trong phn t c 2 nhm Oh
tr ln hay mt nhm OH v mt trung tm giu e, mun tch nc th nn dng xc tc Al2O3/t0 (ngoi ra
nhiu tc gi cn dng I2/t0 tch nc), trnh dng acid mnh tch nc v c th xy ra chuyn v hoc
to vng ete (hn ch sn phm khng mong mun).

Bi 9:
a. C5H4.
b.

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Gii thch mu: Trong nc, D s tautome to cc trng thi lng cc nn momen lng cc ln, hn
na n c h electron lin hp di nn c mu.

Trong mi trng axit mnh th D b bin i v mt h electron lin hp nn b mt mu xanh.

c. Cng thc cu trc ca cc cht l:

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Ta thy phn ng to G v H l phn ng th nucleophin nn n s phi xy ra vng 7 cnh mang

in tch dng. T cc cng thc cng hng, ta thy phn ng s xy v tr 4 (8) hoc 6. Vi tc
nhn c kch thc nh th v tr 4 (8) c u tin do to nhiu trng thi trung gian hn nhng khi
tc nhn c kch thc ln, ta phi xem xt n s nh hng khng gian ca cc nguyn t H ca
vng 5 cnh nn v tr 6 c u tin.
d. Cc ng phn ca I, trong Ia v Ib l ng phn i quang, Ic l hp cht meso.

Bi 10: C 2 p n tha mn:

Bi 11:
a.

Xiclooctatetraen khng phng v tn ti 2 dng: gh v thuyn.

b. Dianion thm do tha mn cc quy tc Hulkel: cc e tho mn quy tc e= 4n + 2, phng, c h e lin

hp kn.
c. C ch.

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d.

Bi 12:
a.

Chng t N l mt nguyn t trong vng.

-H (C7H8O4) : =4 ( 2 nhm axit, 2 ni i), hidro ha H to ra axit heptandioic
-H c th l mt trong cc cht sau:

Vy cu to ca axit tropinic c th l:

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b. Do axit tropinic c to thnh bng cch oxi ha tropinon vi CrO3 nn cng thc ca axit l: A5

c. Qa trnh iu ch 1,3,5-xicloheptantrien t tropinon:

d. un nng tropin trong mi trng baz:

Bi 13: A, B (C9H11NO2, = 5) : tan trong axit, lt tc dng vi NaNO2/HCl to thnh A v B

tng ng c cng cng thc phn t C9H10O3. Vy A, B l amin bc 1.

C ( = 8), c ni i C=C, khi oxi ha to thnh axit terephtalic. Vy cng thc ca C l:

(khng quang hot) (quang hot)

Bi 14:

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a.

b.

Ch bc tch HBr c s ng phn ha to thnh hp cht thm.

Bi 15: Xeton Y c phn ng iodofom nn Y c cng thc l: CH3COC21H43.

Bi 16: B c bt bo ha bng mt tan c trong axit. B l baz nit.

Metyl ha D sau nhit phn sn phm thu c 2-metylbuta-1,3-dien. Vy D l :

Vi D1 l sn phm chnh. Suy ra

Bi 17:

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Bi 18:

Bi 19: A c bt bo ha bng 6, c phn ng cng NaHSO3, khng c phn ng idofom. Vy A c

andehit.
B vi Br2/CCl4 vi s c mt ca HgO to thnh C (1,2,3-tribrom-2-phenylpropan).
Vy A l:

Suy ra:

Bi 20:

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Bi 21:

Bi 22:

Bi 23:
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a, Cng thc cu to ca A l:

b,

c. ng phn lp th dng bn l:

Bi 24:

Bi 25:

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CHUYN 2: C CH PHN NG
Cc bi tp dng ny thng l s pht trin ln ca cc phn ng c bn nh SN, AN,
E2,nn vic u tin m cc bn phi lm c th lm tt loi bi tp ny phi nm tht vng cc
c ch c bn, cc iu kin phn ng c trng c th p dng linh hot. Cc bi tp c ch trong
thi thng kh l kh, v n khng n thun ch l mt phn ng m l mt chui cc phn ng v
cc bn phi xem xt xem trung tm phn ng no phn ng trc, trung tm no phn ng sau. Vy
nn ngoi hc cc phn ng c bn, cc bn nn hc thm cc hiu ng nh hiu ng lin hp, hiu
ng cm ng
C ch phn ng thc cht ch l s dch chuyn ca cc electron to nn cc lin kt mi
hoc ph v lin kt. Cc bn hy tng tng mt trung tm giu e nh mt h nc, nc th chy
t cao xung thp, chy t vng nhiu nc n ni t nc, chy t ni gn h nc n ni xa, nc
mun chuyn t thp ln cao th cn nhng my bm, ty tng loi m nc c th chuyn n ni
thch hp. Trong c ch phn ng cng vy, electron chuyn dch sao cho trng thi trung gian c nng
lng thp nht, bn nht. Electron chuyn dch t ni nhiu electron n ni t electron, electron u
tin chuyn gia cc trung tm gn nhau. Ty vo tng loi cht xc tc m c th dn chng ta n
nhng c ch khc nhau v sn phm khc nhau. Vy nn cc bn hy n gin nhng vn hc
c c th p dng nhun nhuyn trong cc bi tp.
Sau y l mt vi v d gip cc bn tham kho:
Bi 1: Vit sn phm v c ch ca cc phn ng sau:

Bi 2: Vit c ch cho cc phn ng sau:

a.

b.

Bi 3: Vit sn phm v c ch cho phn ng sau:

a.

b.
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