BT Hoa Huu Co

volcmttl@yahoo.com.
vn copyright 2009
Ti liu dnh cho:

Hc sinh chuyn Ha.
Sinh vin cc trng i hc.
Gio vin Ha hc.
08 2009
L i ni u
Ha hc hu c l mt trong nhng b mn rt quan trng trong lnh
vc Ha hc ni ring v phm tr Khoa hc t nhin ni chung. Tuy nhin
hin nay, cc ti liu tham kho v bi tp ha hc hu c l khng nhiu. V
vy vic tng hp cc t liu c mt ti liu tham kho b ch v d tip
thu hn l vic rt cn thit.
Bi tp Ha hc hu c l mt ti liu c bin son da trn vic
tng hp li t nhiu ngun t liu khc nhau theo tng chuyn hc
sinh, sinh vin d nm bt. Ti liu gm hai phn: Phn bi tp theo tng
chuyn v phn hng dn gii. Cc bi tp trong tng chuyn c
tuyn chn k lng nhm mc ch m bo cho cc dng bi tp khng
trng lp v hc sinh, sinh vin c th tip cn nhiu hng ra khc nhau
t cng mt d liu kin thc.
Bi tp Ha hc hu c bao gm hai tp:
- Tp 1: Gm by chuyn tng ng vi ni dung thuc phn i cng
ha hc hu c v phn kin thc ha hu c t bi alkane n cetone
(theo chng trnh ha hc ph thng).
- Tp 2: Gm cc phn t acid carboxylic n cc hp cht d vng. Ngoi
ra cn minh ha thm mt s bi tp nng cao tng hp cc chuyn .
V l ti liu tng hp li cc bi tp nm trong cc gio trnh, sch tham kho bi tp
hu c, cc thi hc sinh gii nn p n cho tng bi khng thay i theo p n ca
tng ti liu tham kho. V vy Bi tp Ha hc hu c khng phi l mt ti liu do mt
nhm tc gi bin son m ch l ti liu tng hp c chn la t cc ngun t liu sn
c. (Tng hp t ngun Internet copyright volcmttl@yahoo.com.vn).
Bi tp Ha Hu C Ti liu dnh cho sinh vin cc trng i hc
Part: 1 HIU NG HA HC
-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Sp xp cc nhm nguyn t sau theo chiu tng dn hiu ng tng ng, bit trong cu a th R
ni trc tip vi S.
a. Hiu ng I ca: (1) SR (2) SO2R (3) SOR
b. Hiu ng C ca: (1) R2NCO (2) R2NC(=NR) (3) (R)2NC(=+NR2)
c. Hiu ng +C ca: (1) RCON(R) (2) RC(=NR) N(R) (3) RCH2N(R)
Bi 2: Da vo hin tng cng hng, vit cng thc gii hn (nu c) ca cc cht sau y:
a. CH2=CHCH2Cl. c. C6H5CN.
b. p-NO2C6H4NH2. d. C6H5CH3.
Bi 3: Gii thch ti sao nhng v tr o- hay p- ca hp cht C6H5CH2Cl tng i giu in t trong khi
ti cc v tr o- hay p- ca C6H5CCl3 th thiu in t.
Bi 4: Da vo hiu ng in t, hy so snh tnh acid ca cc cht sau y:
a. C6H5OH (1), p-CH3OC6H4OH (2), p-NO2C6H4OH (3), p-CH3COC6H4OH (4), p-CH3C6H4OH (5).
b. CH3CH2COOH (1), ClCH2COOH (2), ClC2H4COOH (3), IC2H4COOH (4), ICH2COOH (5).
Bi 5: Sp xp cc cht sau theo th t gim dn tnh base:
(1) (2) (3) (4) (5)

Bi 6: So snh tnh acid ca cc hp cht sau: (1) (CH3)3CCOOH ; (2) CH3CH=CHCH2COOH ;
(3) CH3CH2CH=CHCOOH ; (4) (CH3)2CHCOOH ; (5) CH2=CHCH2CH2COOH.
Bi 7: So snh tnh base ca cc hp cht sau:
(1) (2) (3) (4) (5)
Copyright 2009 volcmttl@yahoo.com.vn 1

Bi 8: Ngi ta nhn thy rng alcohol tertbutylic tc dng ngay lp tc vi acid HCl m c to
thnh tertbutylchloride bn vng trong khi alcohol nbutylic trong cng iu kin phn ng rt chm.
Bi 9: Xc nh hiu ng ca cc nhm th sau khi lin kt vi gc phenyl: Cl, C(CH3)3, CHO, NO2,
CN, CH2CH3, N+(CH3)3.
Bi 10: Da vo hin tng cng hng, vit cng thc gii hn (nu c) ca cc cht sau y:
a. Aniline. c. Vinyl Bromide.
b. Buta1,3diene. d. Acrolein.
Bi 11: So snh bn ca cc ion sau:
a. (1) CH2CH3, (2) CH(CH3)2, (3) C(CH3)3.
b. (1) CH2CH3, (2) CH2OCH3, (3) CH2NHCH3.
c. (1) C(CH3)3, (2) CH2C6H5, (3) CH(C6H5)2.
Bi 12: Xc nh base lin hp ca cc acid sau theo quan im ca Brnsted: H2O, C6H5NH3(+),
C2H5OH, H3O(+).
Bi 13: So snh di lin kt CCl trong CH3CH2Cl v CH2=CHCl. Gii thch.
Bi 14: Gii thch s tng dn nhit si ca cc alcohol sau:
Alcohol CH3OH C2H5OH C3H7OH C4H9OH
Nhit si (oC) 65 78,5 97,2 138
Bi 15: Cho ba gi tr nhit si: 240oC, 273oC, 285oC. Gn ba gi tr trn vo ba ng phn o-, m-, p-
ca benzenediol cho ph hp. Gii thch ngn gn.
Bi 16: Gii thch s khc nhau v nhit si trong dy cc cht sau:
(1) (2) (3) (4)
115oC 117oC 256oC 187oC

Bi 17: So snh kh nng tan trong nc ca cc cht sau
a. (1) HO(CH2)4OH, (2) HO(CH2)3CHO, (3) C3H7CHO.
b. (1) C6H5NH3Cl, (2) C6H5NH2, (3) C2H5NH2.
Bi 18: Acid fumaric v acid maleic c cc hng s phn li nc 1 (k1), nc 2 (k2). Hy so snh cc cp
hng s phn li tng ng ca hai acid ny v gii thch.
Bi 19: So snh nhit nng chy v tr s pKa ca 2 acid sau:
(1) acid iso-Crotonic (2) acid Crotonic

Bi 20: Xc nh tm base mnh nht trong cc alkaloid sau:
Nicotine Vindoline
************************************************
Part: 1 HNG DN GII

Bi 1: Sp xp theo chiu tng dn hiu ng in t:
a. (1) < (3) < (2).
b. (2) < (3) < (1).
c. (1) < (2) < (3).
Bi 2: Vit cng thc gii hn:
a. Cht (a) khng c cng thc gii hn.
b. Cng thc gii hn ca (b)
c. Cng thc gii hn ca (c)
d. Cng thc gii hn ca (d)

Bi 3: Gii thch:
- hp cht C6H5CH2Cl c hiu ng siu lin hp dng +H ca nhm CH2Cl vi vng
benzene lm cho nhng v tr o- hay p- ca vng tr nn giu in t.
- Trong khi nhm CCl3 ht in t mnh (hiu ng siu lin hp m H) nn nhng v tr o-
hay p- ca C6H5CCl3 th thiu in t.
Bi 4: So snh:
a. (3) > (4) > (1) > (5) > (2). b. (2) > (5) > (3) > (4) > (1).
Bi 5: Chiu gim dn tnh base: (3) > (1) > (4) > (5) > (2).
Bi 6: Chiu tng dn tnh acid: (1) < (4) < (3) < (5) < (2).
Bi 7: Chiu gim dn tnh base: (3) > (4) > (5) > (1) > (2).
Bi 8: Xt 2 phn ng sau:
+
(1) (CH3)3COH + HCl
H
(CH3)3CCl + H2O c vn tc phn ng l v1
+
(2) CH3CH2CH2CH2OH + HCl
H
CH3CH2CH2CH2Cl + H2O c vn tc phn ng l v2
C ch phn ng d l SN1 hay SN2 u tri qua giai on to carbocation. Carbocation cng bn th phn
ng xy ra cng u tin. S d v1 >> v2 l do carbocation (CH3)3C bn hn CH3CH2CH2CH2 nhiu.
iu ny gii thch da vo +I ca (CH3)3C ln hn nhiu so vi +I ca CH3CH2CH2CH2.
Bi 9: Khi lin kt vi gc phenyl th:
- CHO, NO2, CN gy hiu ng I, C
- Cl gy hiu ng I, +C
- N+(CH3)3 gy hiu ng I
- C(CH3)3 gy hiu ng +I
- CH2CH3 gy hiu ng +I, +H
Bi 10: Cng thc gii hn:
a. Aniline
+
b. Buta1,3diene: CH2CH=CHCH2

c. Vinyl Bromide: CH2CH=Br+
+
d. Acrolein: CH2CH=CHO
Bi 11: So snh bn:
a. (3) > (2) > (1).
b. (3) > (2) > (1).
c. (3) > (2) > (1).

Bi 12: Xt bng:
acid H2O C6H5NH3(+) C2H5OH H3O(+)
base lin hp OH C6H5NH2 C2H5O H2O
Bi 13: di lin kt CCl trong CH2=CHCl ngn hn trong CH3CH2Cl v:
- CH3CH2Cl c hiu ng I.
- Ngoi hiu ng I cn c thm hiu ng +C lm gim di lin kt CCl

(lm di lin kt CCl ngn hn lin kt CCl bnh thng ng thi lm lin kt C=C di
hn di lin kt C=C bnh thng).
Bi 14: Do c 4 alcohol u to c th to c lin kt hydro lin phn t nhng do khi lng phn t
ca cc alcohol tng dn nn nhit si cng tng dn.
Bi 15: Ta c ba ng phn o-, m-, p- ca benzenediol
(1) 240oC (2) 273oC (3) 285oC

(1) c lin kt hydro ni phn t nn nhit si l b nht.
(2), (3) u c lin kt hydro lin phn t nhng lin kt hydro ca (3) bn hn ca (2) do t b cn tr v
mt khng gian.
Bi 16:
- Ta c nhit si ca (1) < (2) l do hai cht ny khng to c lin kt hydro nn nhit si
ph thuc vo khi lng phn t.
- Li c, nhit si ca (4) < (3) l do mc d c hai cht u c lin kt hydro lin phn t
nhng lin kt hydro ca (3) dng polymer cn ca (4) dng dimer.
Bi 17: Kh nng tan trong nc ca:
a. (1) > (2) > (3). b. (1) > (3) > (2).
Bi 18: Xt cc chuyn ha:
HOOC H - H
HOOC H OOC
H COOH - H+ H COO- - H+ H COO-

, ,,
F Axit fumaric F F
OH ...O OH ... O -
OOC COO-
.... O
....
O OH O
- H+ - H+ H H
H H H H
M Axit maleic M, M,,

- k1(M) > k1(F) l do M c kh nng to lin kt hydro ni phn t, lin kt OH ca M trong qu

trnh phn li th nht phn cc hn so vi F v base lin hp M' cng bn hn F'.
- k2(M) < k2(F) l do lin kt hydro ni phn t lm cho M' bn, kh nhng protone hn so vi
F'. Ngoi ra, base lin hp M'' li km bn hn (do nng lng tng tc gia cc nhm COO
ln hn) base lin hp F''.
Bi 19: So snh
- Nhit nng chy ca (2) > (1).
- Tnh acid ca (1) > (2).
Bi 20: Xc nh tm base mnh nht
Nicotine Vindoline
- Alkaloid l cc base t nhin, tnh base tp trung ti d t N cho nn nguyn t N cng giu
electron th tnh base cng mnh.
- Vi Vindoline th N(b) trong nhn indole c tham gia qu trnh cng hng nn ngho electron
hn N(a) nn tm base mnh nht ca vindoline l N(a).
- Vi Nicotine th tnh base ca N(a) v N(b) gn bng nhau tuy nhin N(a) tham gia vo qu
trnh cng hng cho nn tm base mnh nht ca Nicotine l N(b).
************************************************
Part 2 NG PHN

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Vit cc ng phn cu to ca cc cht sau:

a. C5H10 (cha mt vng). c. C6H14.
b. C5H11OH. d. C4H9Cl.
Bi 2: Cht no sau y c ng phn hnh hc, gi tn cc ng phn theo danh php Z, E.

a. (CH3)2CHCH=CH2 f. Cao su thin nhin
b. CH3CH=CHCH3 g. Nha Guttapercha
c. CH3CH=CHF h. CH3CH=C=C=C=CHCH3
d. C2H5C(CH3)=CHCH3 i. 1,2dimethylcyclopropane
e. CH3CH=C=CHCH3
Bi 3: Da theo gi tr momen lng cc ca cc ng phn hnh hc, hy cho bit trong cc cht A, B
sau y ng phn no l cis, ng phn no l trans
a. FHC=CHF A = 0 D B = 2,42 D
b. CH3CH=CHBr A = 1,57 D B = 1,69 D
c. pNO2C6H4CH=CHC6H4 A = 3,11 D B = 4,52 D
Bi 4: Nhng cht sau y c th tn ti bao nhiu ng phn lp th.
a. 1phenylethanol.
b. 2chlorobut2ene.
c. 1,2dibromopentane.
d. Alanine.
Bi 5: Trnh by cng thc chiu Fischer v xc nh cu hnh tuyt i ca cc ng phn c cu to sau
(a) (b) (c)
Bi 6: Vit cng thc chiu Newman dng bn ca:

a. (CH3)2CHCH2CH3.

b. CH3CH=CH2.
c. CH3CHO.
Bi 7: Cht A l mt acid hu c c ni i C=C v khng quang hot. Tuy nhin A c ng phn hnh
hc v c cng thc phn t l C5H8O2. Khi hydro ha A thu c sn phm B c tnh quang hot. Xc
nh hai cht A, B v vit phng trnh phn ng xy ra.
Bi 8: Vit cc cng thc h bin ca:
a. CH3COCH2CH3.
b. CH3COCH2COCH3.
c. C6H5NHCONHC6H5.
Bi 9: Hy ghi du * vo bn cnh nguyn t carbon bt i v xc nh cu hnh tuyt i ca Serine,
Adrenaline, Menthone.
Serine Adrenaline (Corticoid) Menthone

Bi 10: Vit cng thc dng h bin v cho bit loi h bin trong hai trng hp sau:
a. Cyclohexanone. b. (CH3)2CHN=O.
Bi 11: Xc nh cu hnh ca A, B (dng cis, trans) v vit cu dng gh tng ng
H H
HH HH
A B
Bi 12: Cho cc phn ng sau:
(1) C6H5CH2CH(CH3)OH + ClSO2C6H4CH3-p
pyridine
(E) + +
[ ]D = +33o H Cl
(2) (E) + CH3COOK TsOK + (F) (Ts l k hiu vit tt ca SO4C6H4CH3-p)
(3) (F) + KOH CH3COOK + C6H5CH2CH(CH3)OH
[ ]D = 32,2o
a. Xc nh cu trc ca (E) v (F) v cho bit phn ng (2) thuc loi phn ng g.
b. Cho bit phn ng thy phn cc ester loi nh (F) trong mi trng kim vi s hin din ca

H2O18 nh sau: RCOOR + H2O18

OH
RCOO18H + ROH


Da vo cc kt qu trn, hy gii thch s thay i du nng sut quay cc [ ]D ca alcohol ban u

v sn phm.
Bi 13: Vit tt c cc ng phn ca phc cht [Co(bipy)2Cl2]+ vi bipy l:
N N
Bi 14: Quang ph hp th in t ca formaldehyde c ba cc i 295 nm, 185 nm v 155 nm. Nu

cho formaldehyde tc dng vi H2 c xc tc Pt th ba cc i ny cn khng. Gii thch.
Bi 15: Vit cng thc cu to cc ng phn mch h c cng thc phn t C3H4BrCl, c ng phn
quang hc v ch c mt carbon phi i xng trong phn t.
Bi 16: Styryllactone c phn lp t thc vt. Vit cng thc cu dng cc cp ng phn i quang v gi
tn styryllactone theo danh php IUPAC.
6 5 4
O
7 3
9 O
8
O
1 2
HO
Bi 17: Khung carbon ca cc hp cht terpene

c to thnh t cc phn t isoprene kt ni vi
nhau theo quy tc u ui. V d, nu tm quy
c: (u) CH2=C(CH3)CH=CH2 (ui) th phn
t mycrene c kt hp t 2 n v isoprene.
Da vo quy tc trn hy cho bit trong cc cht sau mycrene
y, cht no l terpene v ch ra n v isoprene trong khung terpene .
Bi 18: Vit cng thc Fischer ca cc cht C v D trong dy chuyn ha sau:
Bi 19: Vit cng thc chiu Fischer cc ng phn lp th ca acid 2bromo3methylsuccinic v ch ra

cc cp ng phn i quang v cc cp ng phn khng i quang trong cc ng phn lp th .

Bi 20: C ba hp cht: A, B v C
a. Hy so snh tnh acid ca A v B.

b. Hy so snh nhit si v tan trong dung mi khng phn cc ca B v C.
c. Cho bit s ng phn lp th c th c ca A, B v C.
Part 2 HNG DN GII

Bi 1: Vit cc ng phn cu to:
5 2 + 2 10
a. bt bo ha = = 1 , theo C5H10 c cha mt vng ( = 1 ) nn l cycloalkane.
2
C5H10 (c 1 vng) c 5 ng phn cu to ph hp:
5 2 + 2 12
b. C5H11OH c bt bo ha = = 0 nn l alcohol no n chc. C 8 ng phn.
2
c. C6H14 c = 0 , c 5 ng phn.
d. C4H9Cl c = 0 , c 4 ng phn.
Bi 2: Cc cht c ng phn hnh hc l b, c, d, f , g, h, i
- Vi b, c, d ch c 2 ng phn hnh hc.
- f (cispolyisoprene) c ng phn l g (transpolyisoprene) v ngc li.
- h c ng phn hnh hc v c s l lin kt C=C lin nhau nh mt h c nh.
- i c hai ng phn hnh hc do vng cyclopropane phng (mt c nh).
Bi 3: Xt bng

Cu
a b c
ng phn
Cis B A B
trans A B A
Bi 4:
a. (A) c 1 C* nn c 21 = 2 ng phn quang hc, (A) khng c ng phn hnh hc. Vy (A) c 2
ng phn lp th.
b. (B) c 2 ng phn lp th l 2 ng phn hnh hc.
c. (C) c 2 ng phn lp th l 2 ng phn quang hc.
d. (D) c 2 ng phn lp th l 2 ng phn quang hc.
Bi 5: Cu hnh tuyt i
(a) (2S)(3S)dichlorobutane.
(b) Acid (2R)(3R)2,3dihydroxy2,3dimethylbutane4al1oic.
(c) (2R)(3S)2bromo3chlorobutane.
(a) (b) (c)

Bi 6: Vit cng thc chiu Newman
a. (A) c 2 dng bn:
b. (B) c 1 dng bn:
c. (C) c 1 dng bn:

Bi 7:
A l CH3CH=C(CH3)COOH.
B l CH3CH2CH(CH3)COOH.
Bi 8: Cng thc h bin
a. H bin cetoenol ca dng ceto CH3COCH2CH3 l cc dng enol
CH3C(OH)=CHCH3 ; CH2=C(OH)C2H5
b. H bin cetoenol ca dng ceto CH3COCH2COCH3 l cc dng enol
CH3C(OH)=CHC(=O)CH3 ; CH2=C(OH)CH2C(=O)CH3
c. H bin cetoenol ca dng ceto C6H5NHCONHC6H5 l dng enol
C6H5N=C(OH)NHC6H5
Bi 9: Ghi du * vo bn cnh nguyn t carbon bt i v xc nh cu hnh tuyt i:
S R
R
Bi 10: Cng thc dng h bin
a. Cyclohexanone. H bin cetoenol
b. (CH3)2CHN=O. H bin nitro-axi
Bi 11: Xc nh cu hnh ca A, B (dng cis, trans) v vit cu dng gh tng ng

- A l cisdecalin - B l transdecalin
- Cu dng gh ca (A), (B)
(A) (B)
Bi 12:
a. Gi s alcohol ban u c [ ]D = +33o cu hnh R => (E) cng c cu hnh R v phn ng
khng xy ra ti C* m ti O, trong khi (F) c cu hnh S ti phn ng xy ra ti C*.
- Gi s cu trc ban u ca alcohol l:
- Cu trc ca (E) l: Cu trc ca (F) l:
- Phn ng (2) l phn ng SN2 => sn phm alcohol ca phn ng (3) c cu hnh nghch vi
cu hnh alcohol ban u.
b. Phn ng (1) v (3) khng lm nghch cu hnh, ngc li phn ng (2) c s nghch o cu hnh
do phn ng xy ra theo c ch SN2
Bi 13: Quy c biu din bipy bng mt cung li.
a. ng phn cis, trans:
Cl
Cl
Co Cl Co
Cis Cl Trans
b. ng phn quang hc:

Cl Cl
Co Cl Cl Co
Bi 14: Ba cc i hp th 295 nm, 185 nm v 155 nm tng ng vi s chuyn di in t mc nng

lng: n * , n * , * . Khi tc dng vi H2/Pt to ra nhm OH nn lin kt khng cn, do vy
ba cc i khng cn.
Bi 15: ng phn quang hc:
Bi 16:
- Tn: 8hydroxy7phenyl2,6dioxabicyclo[3.3.1]nonane3one
- Cng thc cu dng:
4 O O 4 O O
3 3 4 4 3
2 3
2 2 2
O O O O
7 6 5 5 6
7 7 6 5 5 6
H5C 6 O O C6H5 H5C 6 O O 7
C6H5
HO 8
1
9 9
1
8
OH HO 1 1 OH
8 9 9 8
Bi 17: Acoron v acid abietic l terpene
Bi 18: Cng thc Fischer ca cc hp cht C, D

Bi 19: Ta c 4 ng phn lp th
(I) (II) (III) (IV)
Bi 20: So snh, gii thch

a. Tnh acid c nh gi bi s d dng phn li protone ca nhm OH. Kh nng ny thun li
khi c cc hiu ng ko electron (I hoc C) nm k nhm OH. A va c hiu ng lin hp (C)
v hiu ng cm ng (I) ; B ch c hiu ng (I). Tnh acid ca (A) > (B).
b. Lin kt hydro lm tng im si. Cht C c lin kt hydro ni phn t, B c lin kt hydro lin
phn t nn nhit si ca (C) b hn nhit si ca (B). (C) c tan trong dung mi khng
phn cc ln hn (B).
c. (A), (B) u c 2 tm bt i, hai nhm th c th nm 2 pha khc nhau ca vng
cyclohexene v chng c th tn ti 4 ng phn lp th. (C) c 4 tm bt i c 16 ng phn.

Part 3 C CH PHN NG
(- )
O
OEt O O OEt O
OEt O
C C
O N N O N N
N N N
HN N -H +
N +H +
+ CO2 + HN N
O2 S O2 S
N N CH3 N N CH3 O2 S N N CH3
-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Cho bit cc phn ng sau xy ra theo c ch g. Vit c ch phn ng.

a. CH3MgCl + C2H5COCH3 g. 2C2H5OH
H

+
b. CH3CH2Cl + KCN h. Pyridine + C2H5I

c. CH3Cl + H2NCH3 +
i. C6H5OH + HCHO
H

d. CH3CH2Cl + H2O
OH
j. C6H5CHO + CH3CHO
OH

e. C6H5ONa + CH3I o
k. CH3CH2CH(OSO3H)CH3 + H2O
t

f. C6H5OH + CH3OH
l. CH3COOC2H5 + OH
Bi 2: Xc nh cc cht cn li trong cc s sau v nu c ch to ra chng
a. Hon thnh s sau:
b. Hon thnh s sau:
c. Hon thnh s sau:
Bi 3: Cho bit sn phm to thnh trong cc phn ng sau, nu c ch phn ng

o
a. CH3CH=CH2 + Cl2
600 C
1:1

b. CH2=CH2 + Br2
CCl4
1:1

c. H2C=CHCH=CH2 + Br2
CCl4
1:1

o
d. C6H5CH3 + Cl2 t C
1:1,Fe,xt

Bi 4: So snh kh nng phn ng ca cc cp cht sau:

a. Theo SN1: CH3CH2CH2Cl (1) ; CH2=CH2CH2Cl (2).
b. Theo SN2: CH2=CHCl (1) ; CH3CH2Cl (2).
c. Theo SN1: p-NO2C6H4CH2Cl (1) ; p-CH3OC6H4CH2Cl (2) ; CH3CH2CH2Cl (3).
Bi 5: Dng mi tn cong ch r c ch chuyn 7-dehydrocholesterole (I) thnh vitamine D3 (II) v cho bit
cu dng bn ca n. Bit trong cng thc di y: R l: -CH(CH3)-(CH2)3-CH(CH3)2
R R
(I) (II)
HO HO
Bi 6: Cho s phn ng:

CH 3C=O
1. C 6H 5MgBr HBr a
c
C 2H 5 H B C
(A) 2 . H 2O
C 3H 7
a. Vit c ch phn ng v cng thc cu to cc sn phm.

b. Gi tn cu hnh ca B, C theo danh php R, S.
Bi 7: Hy gii thch s to thnh nhanh chng 2,4,6-Br3C6H2NH2 (D) khi cho p-H2N-C6H4-SO3H (A)
hoc p-H2N-C6H4-COOH (B) tng tc vi dung dch nc Br2.
Bi 8: Hy ch ra c ch phn ng v sn phm cui ca phn ng cng Br2 (1:1) vi nhng cht sau:
a. Acid maleic (1).
b. Acid fumaric (2).
c. But-2-ine (3).
H 3C C C CH3
(1) (2) (3)
Bi 9: Xt phn ng th: RCl + OH ROH + Cl c biu thc tc phn ng l: v = k[RCl] hoc
v = k[RCl][OH ]
a. Cho mt v d c th v RCl trong mi trng hp, gii thch.
b. S dung mi gii ca tertButyl bromide trong acid acetic xy ra theo c ch nh sau:
(CH 3 )3 CBr (CH 3 )3 C + + Br (1)
+
(CH 3 )3 C + CH 3COO (CH 3 )3 COCOCH 3 (2)
Hy gii thch ti sao, khi tng hm lng Sodiumacetate (CH3COONa) th khng lm tng tc
phn ng.

Bi 10: Hp cht 2,2,4-trimethylpentane (A) c sn xut vi quy m ln bng phng php tng hp
xc tc t C4H8 (X) vi C4H10 (Y). A cng c th c iu ch t X theo hai bc: th nht, khi c xc
tc acid v c, X to thnh Z v Q ; th hai, hydro ho Q v Z.
a. Vit cc phng trnh phn ng minh ha v tn cc hp cht X, Y, Z, Q theo danh php IUPAC.
b. Ozone phn Z v Q s to thnh 4 hp cht, trong c acetone v formaldehyde, trnh by c ch.
Bi 11: Gii thch:
a. Ti sao phn ng sau khng dng tng hp tert-butyl propyl ether.
CH3CH2CH2ONa + (CH3)3CBr (CH3)3COCH2CH2CH3
b. Sn phm chnh ca phn ng ny l g.
c. Hy ngh phng php tng hp tert-butyl propyl ether tt hn.
Bi 12: X l - halogen cetone vi base mnh to thnh cc sn phm chuyn v. S chuyn v ny gi
l phn ng Favorski: - chlorocyclohexanone s chuyn v thnh methylcyclopentanecacbocylate khi c
mt CH3ONa trong ether. Hy xc nh c ch ca phn ng ny.
Bi 13: Cho cc phn ng sau: But 2 ine

LiAlH 4
A (1) ; But 2 ine H2
Pd / CaCO3
A (2) . Trong
A, B l 2 ng phn lp th. Khi ch ha ring bit A v B bng acid mnh th chng u chu s chuyn
ha sau: ng phn ha v tr, ng phn ha khng gian.
a. Xc nh A, B v cc sn phm chuyn ha nu trn.
b. Vit c ch cho qu trnh chuyn ha trn.
Bi 14: Khi un nng 2methylcyclohexane1,3dione vi but3ene2one trong dung dch kim
ngi ta thu c mt hp cht hu c (sn phm chnh) c cng thc C11H14O2. Hy vit cng thc cu
to ca sn phm ny v gii thch qu trnh to ra n.
Bi 15: C mt phn ng chuyn ha theo phng trnh sau:
a. Gii thch c ch.

b. Nu thay cht ban u l pxylene th sn phm no to thnh.

Part 3 HNG DN GII

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1:
a. CH3MgCl + C2H5COCH3
AN
(CH3)2C(C2H5)OMgCl
2
b. CH3CH2Cl + KCN
SN
CH3CH2CN + Cl
2
c. CH3Cl + H2NCH3
SN
CH3HNCH3 + HCl
2
d. CH3CH2Cl + H2O
SN
CH3CH2OH + HCl
2
e. C6H5ONa + CH3I
SN
+ NaI
f. C6H5OH + CH3OH
SE
CH3C6H4OH (o-, p-) + H2O
2
g. 2C2H5OH
SN
C2H5OC2H5 + H2O
2
h. Pyridine + C2H5I
SN
[pyridine(N+) C2H5]I
i. C6H5OH + HCHO
SE
(o-, p-) CH2OHC6H4OH
j. C6H5CHO + CH3CHO
AN
C6H5CH=CHCHO + H2O
1
k. CH3CH2CH(OSO3H)CH3 + H2O
SN
CH3CH2CH(OH)CH3 +
2
l. CH3COOC2H5 + OH
SN
CH3COO + C2H5OH
Bi 2:

Bi 3:
600o C
a. CH3CH=CH2 + Cl2 SR
Cl CH 2 CH = CH 2 + HCl
b. CH2=CH2 + Br2
CCl4
AE
BrCH2CH2Br
c. H2C=CHCH=CH2 + Br2
CCl 4
AE
(1) + (2) ;
(1) ClCH2CH(Cl)CH=CH2 ; (2) ClCH2CH=CHCH2Cl

o
d. C6H5CH3 + Cl2
t C,1:1,Fe,xt
SE
p CH3C6 H 4Cl + HCl
Bi 4:
a. (2) > (1) b. (2) > (1) c. (2) > (3) > (1)
Bi 5:
. R
H
R
H2C
as
HO HO
to
R
HO
HO
Cu
Cudng
d ngbn
bn: S-trans R
Bi 6:
a. C ch AN. Cng thc ca B v C
b. B: (2R)(3S)2phenyl3ethylhexane2ol, C: (2R)(3S)2phenyl2bromo3ethylhexane
Bi 7: Trong nc (A), (B) tn ti dng ion lng cc:
- p-H2N-C6H4-SO3H (A) p-+H3N-C6H4-SO3 (A)
- p-H2N-C6H4-COOH (B) p-+H3N-C6H4-COO (B)
Mt nhm SO3 trong A hoc COO trong B l do: Br2 Br+ + Br

Sau tc nhn electronphile (Br+) s tn cng vo nguyn t carbon ca nhn thm th nhm SO3
trong A hoc COO trong B. Sau xy ra qu trnh tch H+ to thnh nhm NH2. Nhm NH2 vi
hiu ng C s nh hng nhm th tip theo vo v tr ortho- theo s sau:
Bi 8: C ch cng Bromine vo ni i C=C xy ra theo c ch cng hp electronphile AE, gm 2 bc:
Trng hp a, b xy ra theo c ch AE nu trn.

a. Phn ng to thnh hn hp raxemic gm 2 acid: acid (2R)(3R)2,3dibromobutanedioic v acid
(2S)(3S)2,3dibromobutanedioic
b. C 4 cch tn cng u cho 1 sn phm duy nht l acid (2R)(3S)2,3dibromobutanedioic
c. Cng tng t c ch AE nhng sn phm l: (E)2,3dibromobut2ene.
Bi 9: a. Ta c:
- v = k[RCl] phn ng th n phn t SN1, trng hp thun li l halogenide bc III nh
(CH3)3CCl.
- v = k[RCl][OH] phn ng th lng phn t SN2, trng hp thun li l halogenide bc I nh
CH3CH2CH2Cl
b. Phn ng theo SN1 , m giai on (1) l giai on chm quyt nh tc phn ng v biu thc
tc phn ng khng ph thuc [CH3COO] nn tng nng CH3COONa khng lm thay i
tc phn ng.

Bi 10:
a. Sn phm phn ng
CH3 CH3 CH3 H CH3
o,
t p
H 3C C CH2 + H C CH3 H 3C C C C CH3
CH3 H H CH3
2-Metylpropen (X) 2-Metylpropan (Y) (A)
Phn ng qua 2 bc:
Bc th nht gm tng tc gia hai phn t trong mi trng acid:
CH3 H CH3
CH3 H3C C C C CH2
2 H3C C CH2 H+ CH3 H 2,4,4-trimetyl pent-1-en
CH3 H CH3
H3C C C C CH3
CH3 2,4,4-trimetyl pent-2-en

Bc th hai hydro ho Q v Z
CH3 H CH3
H3C C C C CH2 + H2
CH3 H CH3
CH3 H o
Ni , t
H3C C C C CH3
CH3 H CH3
CH3 H H
H3C C C C CH3 + H2
CH3
b. C ch phn ng
(0,75 m). O O
O O O CH2
O3 Zn/H3O
+
R1 C CH2 R1 C CH2 R1 C O R1 C O + O CH2
CH3 CH3 CH3 CH3

Z
O O CH3
O O O C
CH3 O3 CH3 CH3
R2 C C R2 C C R2 C O
CH3 CH3
H H H
+
Zn/H3O
Q
R2HC O + CH3COCH3

Bi 11:
a. Phn ng sau khng dng tng hp tert-butyl propyl ether.
CH3CH2CH2ONa + (CH3)3CBr (CH3)3COCH2CH2CH3
Natri propoxide tert-butyl bromide tert-butyl propyl ether.
Do phn ng th SN2 khng thc hin vi alkyl halogenide bc ba
b. Ion Alcoholate l mt base mnh, l tc nhn nucleophile nn phn ng tch chim u th nn
sn phm chnh ca phn ng ny l sn phm tch E2
c. Phng php tng hp hiu qu l dng phn t phn ng SN2 c nhm alkyl t cn tr hn v
alcoholate cn tr nhiu hn:
Bi 12:
O O O
O OCH3
Cl CH3O Cl
CH3O
CH3OH
OCH3 O OCH3
O
H2O
OH
Bi 13:
a. Gii thch cu hnh A, B
- Do phn ng cng LiAlH4 l phn ng cng trans nn A l transBut2ene.
- Do phn ng cng H2 xc tc Pd/CaCO3 l phn ng cng cis nn B l cisBut2ene.
b. C ch chuyn ha A B

- ng phn ha v tr
- ng phn ha khng gian

Hai cation trung gian hnh thnh khi protone ha A v B l ng nht nn c th chuyn ha A
thnh B v ngc li.
(B) cation trung gian (A)
Bi 14: Khi un nng 2methylcyclohexane1,3dione vi but3ene2one trong dung dch kim

ngi ta thu c mt hp cht hu c (sn phm chnh) c cng thc C11H14O2.
Bi 15: C ch phn ng
a. Phn ng xy ra qua 4 bc
- Bc 1: To carbocation
H 2O

(CH3 )3C O + H 2
(CH3 )3C OH + H +
(CH 3 )3C+

- Bc 2: To isobutene v isobutane
- Bc 3: To carbocation trung gian
- Bc 4: To sn phm
b. Nu thay bng p-xylene th phn ng theo c ch SE thng thng v s ly ion hydride t nhm
methyl l khng th c. Sn phm l:

Part 4 ALKANE, CYCLOALKANE
-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Tnh nhit phn ng H cho cc phn ng sau y:

a. (CH3)3CH + F2 (CH3)3CF + HF. c. (CH3)3CH + Br2 (CH3)3CBr + HBr.
b. (CH3)3CH + Cl2 (CH3)3CCl + HCl. d. (CH3)3CH + I2 (CH3)3CI + HI.
Cho bit cc gi tr nng lng phn ly lin kt (Kcal/mol):
(CH3)3CH = 93,60 (CH3)3CF = 110,64 HF = 135,84
F2 = 37,20 (CH3)3CCl = 81,36 HCl = 103,68
Cl2 = 58,32 (CH3)3CBr = 67,44 HBr = 87,60
Br2 = 46,32 (CH3)3CI = 52,32 HI = 71,29
I2 = 36,14
Bi 2: Hon thnh cc phng trnh phn ng sau y:
o P
a. CH3CH2CH2CH2CH3 + O2
t
d. CH3CH2I + HI
( red )

b. CH3CH2CH2CH2CH3 + HNO3
e. CH3CH2C(=O)CH3
Zn / HCl
h
c. (CH3)2CHCl + Na
f. CH3CH2CH(CH3)2 + Br2
Bi 3: Cho bit sn phm to thnh khi un nng hn hp kh CH3I v HI. Trnh by c ch v tnh ton
gi tr H cho tng giai on. Bit cc gi tr phn ly lin kt (Kcal/mol): II = 36,24 ; CH3H = 105,26 ;
HI = 71,29 ; CH3I = 57,17.
Bi 4: Vit qu trnh phn ng Br ha cc cht sau vi s c mt ca benzoylperoxide
a. Isopropylbenzene.
b. pchlorotoluene.
Bi 5: Cho isopentane tc dng vi Cl2 (nh sng h ) thu c 4 sn phm vi thnh phn t l nh sau:
1chloro2methylbutane (30%), 1chloro3methylbutane (15%), 2chloro3methylbutane (33%) v
2chloro2methylbutane (22%).
a. Cho bit sn phm no d hnh thnh hn, gii thch.
b. Tnh kh nng phn ng tng i ca cc nguyn t hydro gn vi carbon bc I, II, III.
Bi 6: Vit c ch phn ng ca 2methylpropane v CCl4 c thc hin 130 140o C vi s c mt
ca tert-butylperoxide.

Bi 7: T cyclopropane, hy iu ch 2,3dimethylbutane.
Bi 8: Kh nng phn ng tng i ca cc hydro bc I, II, III i vi phn ng chloridize (phn ng Cl
ha) l 1: 3,8 : 5 tng ng.
a. Tnh lng tng i ca monochlorobutane nhn c khi Cl ha nbutane
b. Tnh phn trm ca cc sn phm khc nhau.
c. Tnh phn trm cc sn phm monochlorated (c Cl ha mt ln) khi Cl ha 2methylbutane.
Bi 9: Ngi ta chuyn ha 100 g CH4 thnh CH3Cl vi hiu sut l 40%. Sau cho ton b lng
CH3Cl va to thnh tc dng vi Na thu ethane (Hiu sut 50%). Sau ngi ta Br ha ethane, sau
khi phn ng kt thc thy thu c 60% bromoethane. Tnh lng bromoethane sau phn ng Br ha.
Bi 10: T isoamyl chloride, hy vit s iu ch 2,3,4,5tetramethylhexane.
Bi 11: Vit cng thc cu to ca cc hp cht sau:
a. 2,6dimethylspiro[4,5]decane.
b. 1,4dimethylspiro[2,2]pentane.
c. Spiro[4,4]nonane.
d. Spiro[3,4]oct1ene.
e. Bicyclo[3.2.1]octane.
f. 2,3dimethyl9isopropylbicyclo[5.3.0]decane.
Bi 12: T hp cht c 3 nguyn t Carbon, vit phng trnh tng hp bicyclo[4.1.0]heptane.
Bi 13: Hon thnh cc phng trnh phn ng sau v cho bit trong mi phn ng, cht no l cht
trung gian hot ng. Gi tn loi phn ng:
a. CH2=CH2 + CH2N2
Cu Zn
b. CH3CH=CH2 + CH2I2
Bi 14: Vit cng thc cu trc cc sn phm ca cc phn ng sau:
a. 2methylcyclopent1ene + CHCl3
(CH 3 )3 COK
A + B.
b. 1 methylcyclopent1ene + CHClBr2
(CH 3 )3 COK
C + D.
Bi 15: Cho nbutane phn ng vi Cl2 theo t l 1 : 1 c chiu sng thu c hn hp A v hn hp kh
B. hp th ht kh HCl trong B cn va 1,6 l dung dch NaOH 1,25M.
a. Vit phng trnh phn ng th ca nbutane vi Cl2 (1 : 1) v nu c ch phn ng.
b. Tnh khi lng hn hp A.
c. Sn phm chnh trong phn ng th trn chim 72,72% khi lng hn hp A. Tnh khi lng
ca sn phm chnh v ph.
d. Hy cho bit nguyn t H nguyn t carbon bc II tham gia phn ng th vi Cl2 d hn nguyn
t H nguyn t carbon bc I bao nhiu ln.
Bi 16: Hai cycloalkane A v B u c t khi hi so vi methane bng 5,25. Khi Cl ha (1 : 1, askt) th
A cho 4 cht cn B ch cho 1 cht. Xc nh A, B v vit cu dng bn nht sn phm Cl ha t B.

Bi 17: Phn ng gia spiropentane vi Cl2 c chiu sng l mt phng php iu ch

Chlorospiropentane (mt sn phm monochlorated):
a. Gii thch ti sao phn ng trn thng c s dng iu ch chlorospiropentane.

b. Nu c sn phm dichlorated (sn phm Cl ha 2 ln) to thnh. Hy nu phng php tch hai
sn phm .
c. Trnh by c ch phn ng Cl ha trn.
Bi 18: Cho s sau:
a. Vit cc phng trnh phn ng theo s chuyn ha trn.

b. giai on chuyn B2 thnh B3, trong iu kin c rt t Br2, ngoi B3 ngi ta cn thu c mt
lng nh alkane B4 khc. Hy xc nh B4 v gii thch s to thnh B4.
Bi 19: Hon thnh s phn ng sau:
Trong s trn: Cc cht A, A1, B, B1, B2D2 u l cc hp cht hu c.

Bi 20: T cyclopropane v cc cht v c thch hp, vit cc phng trnh phn ng iu ch cc
cht sau:
a. Diphenyl. b. Teflon (CF2CF2)n.
************************************************

Part 4 HNG DN GII

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Tnh nhit phn ng H (Kcal/mol):
a. (CH3)3CH + F2 (CH3)3CF + HF H = 115 (Kcal/mol)
b. (CH3)3CH + Cl2 (CH3)3CCl + HCl H = 33 (Kcal/mol)
c. (CH3)3CH + Br2 (CH3)3CBr + HBr H = 15,12 (Kcal/mol)
d. (CH3)3CH + I2 (CH3)3CI + HI H = 6,24 (Kcal/mol)
Bi 2: Hon thnh cc phng trnh phn ng:
a. CO2 + H2O.
b. CH3CH2CH(CH3)NO2, CH3CH2CH2CH2NO2, CH3CH2CH2NO2, CH3CH2NO2, CH3NO2.
c. (CH3)2CHCH(CH3)2.
d. CH3CH3.
e. CH3CH2CH2CH3.
f. CH3CH2[(Br)C(CH3)]CH3.
o
Bi 3: C ch tng giai on v hiu ng nhit phn ng: CH3 I
t
CH 3 + I

1. CH 3 + HI
CH 4 + I ; H = 71, 29 105, 0 = 33, 71 (Kcal / mol)

2. I + CH3 I
I2 + CH3 ; H = 57, 00 36, 00 = 21, 00 (Kcal / mol)
Cng (1) v (2) ta c phn ng: CH3I + HI

I2 + CH4 ; H = 12,71 (Kcal / mol)
Bi 4:
a. Ta c cc qu trnh

C6 H 5CH(CH 3 ) 2
(C6 H 5 COO)2
SR
C6 H 5 C(CH3 ) 2 + C6 H 5COOH

C6 H 5 C(CH3 ) 2 + Br2
C6 H 5CBr(CH 3 ) 2 + Br

C6 H 5CH(CH 3 ) 2 + Br
C6 H 5 C(CH 3 ) 2 + HBr

C6 H 5 C(CH3 ) 2 + Br2
C6 H 5CBr(CH 3 ) 2 + Br...
b. C ch tng t cu a.
Bi 5:
a. 2chloro2methylbutane d to thnh nht v trong phn ng th gc SR, gc t do cng bn th

sn phm cng u tin, m gc (CH 3 ) 2 C CH 2CH 3 c electron t do nm trn carbon bc III nn

bn nht. V vy s kt hp ca gc Cl vi gc (CH 3 ) 2 C CH 2CH 3 l d xy ra nht.
b. Kh nng phn ng tng i ca cc nguyn t hydro gn vi carbon bc I : bc II : bc III
tng ng t l: 1 : 3,3 : 4,4.

Bi 6: Phn ng c thc hin theo c ch gc t do:

(Me3CO)2 2 Me3CO

Me3CO + Me3CH Me3COH + Me3C
Me3C + CCl 4 Me3CCl + CCl3
CCl3 + Me3CH CHCl3 + Me3C
Qu trnh pht trin dy chuyn cho n khi cc gc t do gp nhau => xy ra s ngt mch.
Bi 7: iu ch
Cyclopropane
HBr
CH 3CH3CH 2 Br
Ca / NaOH
CH 3CH = CH 2
HBr
CH 3CHBrCH 3
Na
sn phm.
Bi 8:
a. C 6 nguyn t H hnh thnh 1chlorobutane (A) v 4 H hnh thnh 2chlorobutane (B). T
l nguyn t ca H (I) : H (II) l 3 : 2. Lng tng i ca sn phm l:
(A) = 3 1 = 3 v (B) = 2 3,8 = 7,6
b. Phn trm (A) v (B) l:
3
%A= 100% 28%
10,6
7,6
%B= 100% 72%
10,6
c. C 4 sn phm monochlorated khc nhau:
1chloro2methylbutane (C) 2chloro3methylbutane (E)
2chloro2methylbutane (D) 1chloro3methylbutane (F)
Ta c lng tng i v % cc sn phm l:
Cht Lng tng i Phn trm
6
(C) 6 1=6 100% 28%
21, 6
5
(D) 1 5=5 100% 23%
21, 6
7, 6
(E) 2 3,8 = 7,6 100% 35%
21, 6
3
(F) 3 1=3 100% 14%
21, 6
Bi 9: p s: 40,9 g
Bi 10: iu ch:

Bi 11: Vit cng thc cu to:
(a) (b) (c)
(d) (e) (f)

Bi 12:
Br(CH 2 )3 Br
1.KCN
2.H O +
HOOC(CH 2 )3 COOH
LiAlH 4
HO(CH 2 )5 OH
HBr
Br(CH 2 )5 Br
3

HOOC(CH 2 )5 COOH
1.KCN
2.H3O+
C2 H5 OH
H+
C 2 H 5OOC(CH 2 )5 COOC2 H 5 C2 H5O
Claisen Condensation
Bi 13:
- (a) cyclopropane ; (b) methylcyclopropane.
- Cht trung gian hot ng ca phn ng:
(a) l carbene :CH2.
(b) l carbenoid ICH2ZnI (tin cht ca carbene :CH2).
- Loi phn ng ny l: Phn ng cng hp ng vng.
Bi 14:
a. :CCl2 cng hp cis vo C = C, nhng kt qu l vng ba cnh c th v tr cis hoc trans vi
nhm CH3 to (A) hoc (B):
(A) (B)

b. Anion ClBr2C: c to thnh s mt Br cho carbene ClBrC: ; carbene ny cng vo C = C v

Cl hoc Br s v tr cis so vi nhm CH3 c (C) hoc (D):
(C) (D)
Bi 15:
a. Phng trnh phn ng:
CH3CH2CH(Cl)CH3 (X) + HCl
askt
CH3CH2CH2CH3 + Cl2
CH3CH2CH2CH2Cl (Y) + HCl
C ch phn ng l c ch th gc t do SR: sn phm chnh l (X), sn phm ph l (Y).
b. m A = 1,6 1,25 92,5=185
c. Khi lng mi sn phm:
185 72, 72
mX = = 134,532g ; m Y = 185 134,532 = 50, 468g
100
d. Gi kh nng phn ng th bi Cl2 ca mt nguyn t H lin kt vi nguyn t carbon bc II l a,
bc I l b ta c:
4a a
100 = 72, 72 109,12a = 436,32b = 3, 998 4
4a + 6b b
Bi 16:
a. MA = MB = 16.5,25 = 84 g/mol A v B l ng phn ca nhau (v u l cycloalkane). Gi
CTPT ca A, B l CxHy ( x 3 ; 6 y 2x ) 12x + y = 84 CTPT ca A, B l C6H12.
- Khi mono-Cl ha B thu c mt hp cht duy nht B l cyclohexane.
- Khi mono-Cl ha A thu c 4 hp cht V vy A c th l methylcyclopentane hoc
A l iso-propylcyclopropane.
b. Cu dng (gh) bn nht ca sn phm mono-Cl ha t B l echlorocyclohexane.

Bi 17:
a. Do cu trc ca spiropentane l i xng, cc nguyn t H trn nhm methylene u nh nhau,
do phn ng mono-Cl ha c th xy ra trn bt c nhm methylene no.
b. Tch bng phng php chng ct phn on v sn phm mono-Cl ha c nhit si thp hn
sn phm di-Cl ha.
c. Phn ng xy ra theo c ch th gc t do SR.
Bi 18:
a. Hon thnh s phn ng:
o
(1) C4H10
t
CH3CH=CH2 + CH4
o
(2) CH3CH=CH2 + H2
Ni / t
CH3CH2CH3
(3) CH3CH2CH3 + Br2
askt
CH3CHBrCH3 + HBr
(4) CH3CHBrCH3 + Mg
Ether khan
(CH3)2CHMgBr
(5) (CH3)2CHMgBr + C2H5Br (CH3)2CHCH2CH3 + MgBr2
o
(6) (CH3)2CHCH2CH3
xt,t
CH2=CCH3CH=CH2 + 2H2
o
(7) n CH2=CCH3CH=CH2
xt,t
(CH2CCH3=CHCH2)n
o
(8) 2CH 4
1500 C
lanh nhanh
HC CH + 3H 2
o
(9) HC CH + 2H 2
Ni / t
CH3 CH3
(10) CH3CH3 + Br2

askt
CH3CH2Br + HBr
o
(11) 3HC CH
Carbon ,600 C
C6H6
(12) C6H6 + CH2=CHCH3
H 2SO 4
C6H5CH(CH3)2
o
(13) C6H5CH(CH3)2 + Br2
Fe,t
p-BrC6H4CH(CH3)2 + HBr
(14) p-BrC6H4CH(CH3)2 + Br2
askt
p-BrC6H4CBr(CH3)2 + HBr
(15) C6H5CH(CH3)2 + HNO3
H 2SO 4
p-O2NC6H4CH(CH3)2 + H2O
b. B4 l n-butane
To thnh B4 l do phn ng th gc t do SR ca C2H6 vi Br2 nh sau:
(1) Br Br
askt
2Br
(2) CH 3 CH 3 + Br CH 3 CH2 + HBr
CH3 CH 2 + Br2 CH3CH 2 Br + Br
CH3 CH3 + Br CH3 CH 2 + HBr...
(3) CH 3 CH2 + Br CH 3CH 2 Br
Br + Br Br2
CH3 CH2 + CH 2 CH 3 CH 3CH 2 CH3CH 2

Bi 19:
Cht Cng thc cu to Cht Cng thc cu to
A CH2=CH2 B1 CH2=CHCH2Cl
B C2H5OH C1 ClCH2CHOHCH2Cl
C CH3CHO D1 HOCH2CHOHCH2OH
D CH3COOH B2 CH3CHClCH3
G CH2=CHCH=CH2 C2 (CH3)2CHMgCl
A1 CH3CH=CH2 D2 (CH3)2CHCH2CH2OH
Ngoi ra:
- Nu C l CH3COOH th D l (CH3COO)2Ca
- Nu A l CH4 th B l HC CH , C l CH3CHO
Bi 20:
o o
a. C3 H8
t
CH 4
1500 C
C 2 H 2 C
600o C
C6 H 6
H2
xt,t o
cyclohexane
Cl2 ,askt
1:1
methylcyclohexane
o
+ C6 H 6

AlCl ,t o
phenylcyclohexane
xt,t
diphenyl
3
o
b. HC CH
H2
Ni,t o
C 2 H 6
Cl2
to
C 2Cl6 HF
SbCl ,t o ,p
CClF2 CClF2
Zn
CF2 = CF2
xt,t ,p
teflon
5
************************************************
Part 5 ALKENE, ALKINE, DIENE, TERPENE

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Bi 1: Hon thnh cc phng trnh phn ng di y v biu din ng phn lp th ca cc sn phm

to thnh bng cng thc chiu Fischer.
a. cisbut2ene + Br2 c. Acid fumaric + Br2
b. transbut2ene + Br2 d. Acid maleic + Br2
Bi 2: Phn ng sau cho sn phm l hp cht mesomeric hay bin th racemic:
trans3,4dimethylhex3ene + H2
PtO 2
sn phm.
Bi 3: Cho bit sn phm to thnh khi ozone ha cc hp cht sau y:
a. CH3CH=CH2.
b. CH2CHCH(CH3)CH=CH2.
c. 1methylcyclohexa1,4diene.
Bi 4: Vit cc qu trnh iu ch:
a. CH3CH2COCH(CH3)2 t propene, HCl, Mg, BH3, H2O2, NaOH, CrO3.
b. Cyclopentanone t cyclobutene, O3, Zn/CH3COOH, LiAlH4, PBr3, Mg, HCOOCH3, CrO3.
Bi 5: em dn xut halogen C6H13I un nng vi dung dch KOH/alcohol thu c sn phm (A). Cho
(A) tc dng vi O3 thy to thnh hp cht ozonide (B). Thy phn (B) cho CH3CHO v aldehyde
isobutyric. Xc nh cng thc cu to ca C6H13I, (A) v (B).
Bi 6: Vit phn ng DielsAlder ca Buta1,3diene vi cc hp cht sau y:
a. Anhydride maleic.
b. Methylvinylcetone.
c. Acid maleic.
d. Acid fumaric.
e. H2C=CHCH=CH2.
f. C6H5CH=CHNO2.
Bi 7: Cho bit sn phm to thnh khi cho isobutene tc dng vi cc cht sau:
a. HI. e. KMnO4 long (lnh).
b. HI (Peroxide). f. 1. O3 ; 2. (CH3)2S.
c. Br2/H2O. g. 1. B2H6 ; 2. H2O2/OH.
d. Br2 + NaCl (H2O).
Bi 8: Cho bit sn phm chnh to thnh khi cho CH3 C CLi tc dng vi cc hp cht sau y:
a. CH3CH2Br. c. Cyclohexanone.
b. Cyclopentanal. d. CH3 CH CH2
Bi 9: Hon thnh chui phn ng sau y:

HC CH
BrMgC CMgBr A
1.CH 3COCH3
2.H O +
B
C2 H5 MgBr
C
1.CO 2
2.H O +
D
3 3

Bi 10: Khi cho isobutene vo dung dch c ha tan HBr, NaCl, CH3OH c th to ra nhng cht g, gii
thch v vit c ch phn ng.
Bi 11: Cho dn xut halogen CH3CH=CHCH2Cl (A)
a. Cho (A) tc dng vi dung dch Cl2 trong bng ti. Vit cng thc cu to ca sn phm.
b. Nu un nng (A) vi dung dch kim long thu c monoalcohol tng ng. Cho thm kim
vo, tc phn ng khng thay i. Hy cho bit c ch phn ng v so snh kh nng phn ng
ca (A) vi n-CH3CH2CH2CH2Cl v CH2=CHCH2Cl trong cng iu kin phn ng, gii thch.
Bi 12: Hydrocarbon (X) c trong tinh du tho mc. Khi cho (X) tc dng vi lng d acid HCl thu
c sn phm duy nht c cha 2 nguyn t chlorine trong phn t. Ozone phn (X) thu c hn hp
(CH3)2CHCOCH2CHO v CH3COCH2.
a. Xc nh cng thc cu to ca (X). Vit cc phng trnh phn ng xy ra.
b. Hydrocarbon (Y) cng c cng cng thc phn t vi (X). Khi ozone phn (Y) thu c (Z) c
cng thc phn t C10H16O2. Cho bit (Z) c cu to i xng v c mch carbon khng phn
nhnh. Xc nh cng thc cu to ca (Y) v (Z).
Bi 13: Khi un nng hn hp Buta1,3diene v ethene thy xy ra phn ng ng vng DielsAlder
to thnh cyclohexene. Phn ng ny tr nn d dng hn nu thay H trong ethene bng nhm ht
electron nh COOH, COOR, CHO, v thay H trong buta1,3diene bng nhm y electron nh
CH3, C2H5,
a. Vit phng trnh phn ng xy ra khi cho Buta1,3diene tc dng vi ethene, cho bit cu trc
ca Buta1,3diene trc phn ng (scis hay strans).
b. un nng transpenta1,3diene vi acid acrylic CH2=CHCOOH, vit cu to sn phm chnh.
c. So snh tc phn ng ca mi diene sau vi acid acrylic.
- 2methylbuta1,3diene v 2chlorobuta1,3diene.
- Cispenta1,3diene v transpenta1,3diene.
Bi 14: Khi trng hp Buta1,3diene to cao su Buna thng to ra sn phm ph l vng 6 cnh
cha no (phn ng DielsAlder), khi phn ng vi H2 d xc tc Ni th to ra ethylcyclohexane. Vit cc
phng trnh phn ng v cho bit iu kin phn ng ng vng DielsAlder xy ra d dng.
Bi 15: C 2 hydrocarbon (A), (B) u c cng thc phn t l C7H14. Bit rng:
- Oxygen ha (A) bng dung dch KMnO4/H2SO4 to ra 2 cht CH3CH2COCH3 v CH3CH2COOH.
- (B) c cu to mch thng v khi oxygen ha bng dung dch K2Cr2O7/HCl to ra CO2.
Xc nh cng thc cu to ca (A), (B) v hon thnh cc phng trnh phn ng.
Bi 16: Mt alkene sau khi ozone phn to ra sn phm hu c duy nht l CH3CHO. Khi cng hp vi
Br2 trong bnh lm bng vt liu phn cc th ch to ra mt sn phm l mt ng phn khng quang
hot. Hy cho bit cng thc phn t ca alkene v vit cng thc cu to ca sn phm theo Fischer,
Newman ri gi tn sn phm.

Bi 17: Alkene (A) c cng thc phn t l C6H12 c ng phn hnh hc, tc dng vi dung dch Br2 cho
hp cht dibromine (B). Cho (B) tc dng vi KOH trong alcohol un nng thu c alkadiene (C) v
mt alkine (D). Khi (C) b oxygen ha (oxygenize) bi dung dch KMnO4/H2SO4 v un nng thu c
acid acetic v CO2. Xc nh (A), (B), (C), (D) v vit cc phng trnh phn ng xy ra.
Bi 18: Khi cyclotrimer ha buta1,3diene vi s c mt ca cht xc tc c kim, ngi ta iu ch
c (Z, E, E)cyclodeca1,5,9triene. y l mt phng php n gin iu ch hydrocarbon vng
ln. Khi dng cc cht xc tc thch hp l cc phc allyn ca kim loi chuyn tip, ngi ta iu ch
c (E, E, E)cyclodeca1,5,9triene v (Z, Z, E)cyclodeca1,5,9triene. Vit cng thc cu to ca
cc hp cht trn.
Bi 19: Ozone phn mt terpene (A) C10H16 thu c mt cht (B) c cu to nh sau:
CH3 C CH2 CH CH CH2 CH = O
O C
H3C CH3
Hydro ha (A) vi xc tc kim loi to ra hn hp sn phm (X) gm cc ng phn c cng thc phn
t C10H20.
a. Xc nh cng thc cu to ca (A).
b. Vit cng thc cc ng phn cu to trong hn hp (X).
Bi 20: T mt loi tinh du ngi ta tch c cht (A) v (B) l ng phn hnh hc ca nhau. Kt qu
phn tch cho thy (A) ch cha 78,95% C v 10,52% H v khi lng, cn li l O. T khi hi ca A so
vi H2 l 76. (A) phn ng c vi dung dch AgNO3/NH3 cho kt ta Ag v mui ca acid hu c. Khi
b oxygen ha (oxygenize) mnh, (A) cho mt hn hp sn phm gm acetone, acid oxalic v acid
levulinic CH3COCH2CH2COOH. Khi cho Br2/CCl4 phn ng vi (A) theo t l mol 1 : 1 thu c ba dn
xut dibromine. Phn t (A) bn hn (B). Xc nh cng thc cu to ca (A), (B).
Bi 21:
1. Hp cht A (C10H18O) c phn lp t mt loi tinh du Vit Nam. A khng lm mt mu nc
bromine v dung dch thuc tm long, cng khng tc dng vi hydro c xc tc Ni, nhng li tc
dng vi HCl m c sinh ra 1chloro4(1chloro1methylethyl)1methylcyclohexane. Hy
xut cu trc ca A.
2. Hp cht B (C10H20O2 ) c trong mt loi tinh du Nam M. T B c th tng hp c A bng
cch un nng vi acid.
a. Vit cng thc cu to v gi tn B.
b. Dng cng thc cu trc, vit phng trnh phn ng v trnh by c ch y ca phn ng
tng hp A.
3. Hp cht B thng c iu ch t C (2,6,6trimethylbicyclo[3.1.1]hept2ene) c trong du
thng. Dng cng thc cu to, vit phng trnh phn ng v ch r cc lin kt ca C b t ra.

4. Trong cy long no c hp cht D tn l 1,7,7trimethylbicyclo[2.2.1]heptan2one. Vit s cc

phn ng tng hp D t C v cho bit c ch ca giai on u.
5. V cu to ha hc, cc hp cht A, B, C v D trn c c im g chung nht. Minh ha vn tt
c im trn cc cng thc cu to ca chng.
Bi 22: Anethole c phn t khi l 148,2 v hm lng cc nguyn t: 81,04% C, 8,16% H, 10,8% O.
(Bit H = 1,008 ; C = 12,000 ; O = 15,999). Hy:
a. Xc nh cng thc phn t ca anethole.
b. Vit cng thc cu trc ca anethole da vo cc thng tin sau:
- Anethole lm mt mu nc bromine.
- Anethole c hai ng phn hnh hc.
- S oxygen ha anethole to ra acid methoxybenzoic (M) v s nitro ha M ch cho duy nht acid
methoxynitrobenzoic.
c. Vit phng trnh ca cc phn ng: (1) anethole vi bromine trong nc ; (2) oxygen ha
anethole thnh acid methoxybenzoic ; (3) nitro ha M thnh acid methoxynitrobenzoic. Vit tn
ca anethole v tt c cc sn phm hu c nu trn theo danh php IUPAC.
d. V cu trc hai ng phn hnh hc ca anethole.
Bi 23: Tin hnh phn ng gia 3,5,5trimethycyclohex2enone v n-butylmagnesiumiodide. Sau ,
thy phn hn hp bng dung dch HCl 4M thu c hp cht B. B b chuyn thnh nm ng phn, k
hiu t D1 n D5 c cng thc phn t C13H22. Vit cng thc cu to ca cc ng phn D1, D2, D3, D4,
D5 v gii thch s hnh thnh chng.
Bi 24: Mt monoterpenoid mch h A c cng thc phn t C10H18O (khung carbon gm hai n v
isoprene ni vi nhau theo qui tc uui). Oxygen ho A thu c hn hp cc cht A1, A2 v A3.
Cht A1 (C3H6O) cho phn ng iodoform v khng lm mt mu nc bromine. Cht A2 (C2H2O4) phn
ng c vi Na2CO3 v vi CaCl2 cho kt ta trng khng tan trong acid acetic ; A2 lm mt mu dung
dch KMnO4 long. Cht A3 (C5H8O3) cho phn ng iodoform v phn ng c vi Na2CO3.
a. Vit cng thc cu to ca A1, A2 v A3.
b. V cng thc cc ng phn hnh hc ca A v gi tn theo danh php IUPAC.
Bi 25: T benzene v cc hp cht hu c c s C 3, vit s tng hp cis-1-phenylhex-2-ene.
Bi 26: Hon thnh s phn ng sau, xc nh cc hp cht t A n I:
o
X
PCl5
A
1.Mg,ether khan
2. CH 2 =C(CH 3 )-CHO
B
1.LiNH 2
2.C6 H13 Br
C
t
D
H2
Pd/C
E
CH3 MgI
ether khan
F
Ac2 O
I(C19 H 38O 2 )
Cho bit: X l:
A c 1H ethylenic, B c 5H ethylenic, D c 1H ethylenic.

Bi 27: A, B l hai hydrocarbon c tch t du m c cc tnh cht vt l v d kin phn tch nh sau:
ts (oC) tnc (oC) %C %H
A 68,6 -141 85,63 14,34
B 67,9 -133 85,63 14,34
A cng nh B lm mt mu nhanh chng dung dch KMnO4 v nc bromine, khi ozone phn cho sn
phm ging nhau. Xc nh cu trc ca A, B.
Bi 28: Hon thnh s phn ng sau:
1.NaNH 2
HC CNa HC CNa 2.Na/NH
CH3CH 2 CH 2 I A
NaNH 2
Br-(CH 2 )4 -Cl
B
NaI
S 2
C D
3.H 2 O
3(l)
E(C11H18 )
1.CH 3MgBr
2.CO 2
F
N
F
G(C12 H 20O 2 ).
H 2 (1mol)
Pd/CaCO3
Bi 29: Pheromol (H) c Bestmann iu ch nm 1982 nh sau:

HC CLi
Me(CH 2 )8 Br
A
1.EtMgBr
2.HC C-CH 2 -OTs
B
1.EtMgBr
2.Epoxide
C 2H 2
Pd,Lindlar
D
bromine ha
CBr4 +PPh 3
E ( C16 H 29 Br )
E NaI
acetone
F
Ph 3 P
G
1.Base
2.CH 2 =CH-CHO
H .
Xc nh cng thc cu to cc cht t A n G. Bit H l:

Bi 30: Acid Abscisic (ABA) thuc loi sesquiterpenoid c nhiu trong gii thc vt c tc dng iu
chnh gic ng ng ca cy ci v cho php cy tn ti trong mi trng bt li. C nhiu phng php
tng hp ABA. y dn ra phng php i t acetone.
+
H
3CH 3COCH 3 NaNH
2
A -2H
2O B(C19 H13O) p-CH
HOCH 2 CH 2 OH
C(C11H18O 2 )
3C6 H 4SO3 H
D(C11H18O 2 )
D KMnO
OH
-
4
[E](C11H 20 O 4 ) KMnO
OH
-
4
F(C11H18O 4 ) CH
3SO 2 Cl

pyridine
G(C11H15O3 )
Tip theo s ni mch to thnh acid nh sau:

Methyl - 3 - methylpent - 2(Z) - ene - 4 - inoate LDA
H (Li + C7- H 7 O 2 ) G I(C18 H 22 O5 Li) H
2O
K CrSO

DMF
4
L
+
L NH
4
H 2O
M 1.CH

2.H +
3 ONa,H 2 O
acid Abscisic (ABA).
a. Vit CTCT cc cht t A n M bit rng hn hp methanesunfonyl chloride/pyridine dng

tch nc alcohol bc ba.
b. Acid Abscisis c tnh quang hot hay khng, n c cu hnh nh th no.
************************************************
Part 5 HNG DN GII

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Biu din cu hnh sn phm bng cng thc chiu Fischer:

Bi 2: Hn hp racemic
Bi 3:
a. CH3CHO + HCHO.
b. OHCCHCH3CHO + 2HCHO.
c. OHCCH2COCH3 + OHCCH2CHO
Bi 4:
a. CH3CH = CH 2
HCl
CH 3 CHCl CH3
Mg
CH3 CH(MgCl) CH3 (1)
CH3CH = CH 2
1.BH3
2.H O ,OH
CH 3CH 2 CH 2 OH
CrO3
CH 3CH 2CHO (2)
2 2
+
(1) + (2)
H 3O
CH3CH 2 CHOH CH(CH 3 ) 2
CrO3
CH3CH 2 CO CH(CH 3 ) 2 .
b. cyclobutene
1.O3
2.Zn/CH 3COOH
OHCCH 2CH 2CHO
LiAlH 4
HO(CH 2 ) 4 OH
1.PBr3
2.2Mg
BrMg(CH 2 )4 MgBr

1.HCHO
2.H O +
cyclopent an ol
CrO3
cyclopen tan one.
3
Bi 5: C6H13I l
Bi 6:

Bi 7:
a. tert-butyliodide.
b. Tert-butyliodide.
c. 1bromo2methylpropanol.
d. 1-bromo-2-chloro-2-methylpropane, 1,2-dibromo-2-methylpropane, 1-bromo-2-methylpropanol.
e. 2methylpropan1,2diol.
f. Acetone v formaldehyde.
g. Isobutanol.
Bi 8:
a. CH3 CH 2 C C CH 3 .
b. Sn phm l
c. Sn phm l
d. CH3 CHOH CH 2 C C CH 3
Bi 9:
A l HC CMgBr ; B l ; C l ; D l
Bi 10: Sn phm phn ng l hn hp gm:

(CH3)3CBr ; (CH3)3COH ; CH3[(HO-)C(-Cl)]CH3 ; (CH3)3COCH3

Gii thch da vo c ch phn ng:
- Trong dung dch c cc qu trnh phn ly:
HBr H+ + Br NaCl Na+ Cl
- Do trong dung dch c 4 tc nhn l Br, Cl, H2O v CH3OH c kh nng kt hp vi
carbocation. Phn ng theo c ch cng electrophile (AE).
- u tin, H+ tn cng vo C to carbocation (CH3)3C (giai on chm.)
- Sau 4 tc nhn trong dung dch s kt hp carbocation to sn phm (giai on nhanh).
Bi 11:
a. CH3CHClCHClCH2Cl. C ch AE.
b. C ch SN1: CH3CH=CHCH2Cl > CH2=CHCH2Cl > CH3CH2CH2CH2Cl.
Bi 12:
a. Cng thc ca X l:
b. Cng thc ca Y v Z ln lt l:
Bi 13:
a. Buta1,3dien dng s-cis. Phn ng:
b. Phn t penta1,3diene c nhm CH3 y electron cn acid acrylic c nhm COOH ht electron
nn c s phn cc cc lin kt theo chiu mi tn cong. Sn phm chnh to thnh do cc nguyn
t C mang in tch tri du kt hp vi nhau.
c. So snh kh nng phn ng:

- 2methylbuta1,3diene > 2chlorobuta1,3diene.

- Cispenta1,3diene < transpenta1,3diene.
Bi 14:
a. Phng trnh phn ng:
to, xt to, xt
+ ; + 2H2
b. iu kin: Hp cht diene (A) phi c cu hnh s-cis. Phn ng ny tr nn d dng hn nu thay
H trong dienophile bng nhm ht electron nh COOH, COOR, CHO, v thay H trong
diene bng nhm y electron nh: CH3, C2H5,
Bi 15:
A l 3methylhex3ene.
B l Hept1ene.
Bi 16:
- Alkene l But2ene
- Phn ng cng Br2 vo But2ene l cng trans nn to ng phn khng quang hot th
alkene But2ene phi dng trans.Cng thc Fischer, Newman ln lt l:
Bi 17:
(A) l: CH3CH2CH=CHCH2CH3. (C) l: CH3CH=CHCH=CHCH3.
(B) l: CH3CH2CHBrCHBrCH2CH3. (D) l: CH3CH 2 C = CCH 2 CH3 .
Bi 18: Cng thc cu to:
Z, E, E E, E, E Z, Z, E
Bi 19:

a. Cng thc cu to ca A:
b. Hn hp X:
Bi 20:
(A) l trans- (CH3)2C=CHCH=C(CH3)CH2CH2CHO.
(B) l cis- (CH3)2C=CHCH=C(CH3)CH2CH2CHO.
Bi 21:
1. Xc nh cng tc cu trc ca A(C10H18O). A c = 2 .
- A khng lm mt mu dung dch nc bromine v dung dch thuc tm long chng t trong A
khng c ni i hay ni ba.
- A khng tc dng vi hydro trn cht xc tc Ni chng t trong A khng c nhm chc carbonyl.
- A tc dng vi acid HCl c c 1chloro4(1chloro1mehylethyl)1methylcyclohexane
nn trong A c vng no v c lin kt ether.
- Suy ra cng thc cu trc ca A
CH3 CH3 CH3
H3C O
O
O
O CH3
CH3
2.a. Vit cng thc cu to, gi tn B

B l mt diol c b khung carbon nh A
Gi tn B: 1-hydroxy-4-(-1-hydroxy-1-methylethyl)-1-methylcyclohexane.
OH
+
H A
H2O
OH
B
2. b. Dng cng thc cu trc, vit phng trnh phn ng v trnh by c ch y ca phn ng.

- C 2 dng trans v cis ca B u cu dng gh bn vng, tuy vy cu dng gh khng th tham

gia ng vng m phi i qua dng thuyn km bn.
- Dng thuyn s tham gia phn ng SN1 ni phn t.
(+)
OH
OH
OH OH OH H
+
H
+ O
OH
(+)
Cis-B H
+
A
(+)
OH
OH OH
OH OH + O
H
OH
(+)
Trans-B H
+
A
3. Lin kt ca C b t cc ng chm chm:
OH
+
2 H2O H
+
OH
4. HO O
Cl
HCl H2O O
C D
H+ Cl-
(+) (+)
chuyn v
5. c im chung nht v cu to ho hc: mi phn t gm 2 n v isoprene (hoc isopentane) ni

vi nhau.
Bi 22:

a. Xc nh cng thc phn t:

C = (81,04/12,00) = 6,75 ; H = (8,16/1,01) = 8,08 ; O = (10,8/16,0 = 0,675
C = 6,75/0,675 = 10 ; H = (8,08/0,675 ) = 12 ; O = 1 => C10H12O
b. Vit cng thc cu trc ca anethole:
Anethole lm mt mu nc bromine nn c lin kt i ; v tn ti dng hai ng phn hnh hc
(lin kt i, ) v khi oxygen ha cho acid nn c lin kt i mch nhnh ; v ch cho 1 sn phm sau
khi nitro ha nn nhm methoxy v tr 4 (COOH- nhm th loi 2, methoxy nhm th loi 1. l acid
4-methoxy-3- nitrobenzoic.
Vy anethole l:
c. Cc phng trnh phn ng:

(1) anethole vi Br2/H2O
(2) oxygen ha anethole thnh acid methoxybenzoic:
(3) nitro ha M thnh acid methoxynitrobenzoic:
Tn ca anethole v tt c cc sn phm hu c nu trn theo danh php IUPAC:

(2) 2-Bromo-1-(4-methoxiyphenyl) propan-1-ol.
(3) Acid 4-methoxybenzoic ; (4) Acid 4-methoxy-3-nitrobenzoic.
d. Hai ng phn hnh hc ca anetol:
(E)-1-methoxy-4-(1-propenyl)benzene (Z)-1-methoxy-4-(1-propenyl)benzene

hoc (E)-1-(4-methoxyphenyl) prop-1-ene hoc (Z)-1-(4-methoxyphenyl) prop-1-ene

Bi 23: Cng thc cu to ca 5 ng phn, k hiu t D1, D2, D3, D4 n D5
Bi 24: a. Xc nh A1, A2, A3

- A l hp cht mch h nn c 2 ni i
- A1 tham gia phn ng iodofom nn A1 l hp cht metyl xeton
CH3COCH3 + I2 /KOH CHI3 + CH3COONa
- A2 phn ng vi nn y l mt acid, da vo cng thc phn t y l mt diacid
HOOC-COOH + Na2CO3 NaOOCCOONa + H2O + CO2
- A3, C5H8O3, cho phn ng iodoform, phn ng c vi Na2CO3. A3 va c nhm chc methyl
cetone va c nhm chc acid.
Vy A1: CH3COCH3, A2: HOOCCOOH, A3: CH3COCH2CH2COOH
b. A l monoterpene mch h nn c b khung carbon l:
Da vo cu to ca A1, A2, A3 nn xc nh c v tr cc lin kt i trong mch carbon (hnh trn):

V c s hnh thnh acid oxalic nn A c th l: (E) hoc (Z)3,7dimethylocta2,6dienol
Bi 25: S tng hp:

HC CH
1.NaNH 2
2.CH 3CH 2 CH 2 Br
CH 3CH 2CH 2C C H
1.NaNH 2
2.C6 H5 CH 2 Br
CH3CH 2CH 2C CCH 2C6 H5 H2
xc tc Lindlar

cis-1-phenylhex-2-ene. Trong : HC CH C
600o C
C6 H 6
CH 3 Br
AlBr3
C6 H 5CH3
Br2 ,as
C6 H5CH 2 Br.
Bi 26:

Bi 27: Da vo kt qu phn tch nguyn t, A v B c cng thc C6H12. c th l ng phn

cis/trans ca hex2ene hoc hex3ene. Do ozone ha cho sn phm ging nhau nn l ng phn ca
hex3ene. A l ng phn cis v c nhit nng chy thp hn vo nhit si cao hn => B l trans.
Bi 28:
HC CNa
CH3CH 2 CH 2 I C3 H 7 C CH
NaNH 2
Br-(CH 2 )4 -Cl
n - PrC C(CH 2 )3 CH 3
NaI
S 2
n - PrC C(CH 2 )3 CH 2 I
N
1.NaNH 2
HC CNa 2.Na/NH 3(l)
n - PrC C(CH 2 ) 4 C CH
3.H 2 O
Trans - n - PrCH = CH(CH 2 )4 C CH
1.CH3 MgBr
2.CO 2

Trans - n - PrCH = CH(CH 2 ) 4 C C - COOH
H 2 (1mol)
Pd/CaCO3
Acid dodeca - 2Z,8E - dienoic (C12 H 20 O2 ).
Bi 29:
t R l CH3(CH2)8:
HC CLi
RBr
HC CR(A)
1.EtMgBr
2.HC C-CH 2 -OTs
HC CCH 2 C CR(B)
1.EtMgBr
2.Epoxide
RC CCH 2 C CCH 2 CH 2 OH(C)
2H 2
Pd,Lindlar
(Z, Z)RCH = CHCH 2 CH = CHCH 2 CH 2 OH(D)
bromine ha
CBr4 +PPh 3
(Z, Z)RCH = CHCH 2 CH = CH(CH 2 ) 2 Br(E)
+
NaI
acetone
(Z, Z)RCH = CHCH 2 CH = CH(CH 2 ) 2 I(F)
Ph 3P
(Z, Z)RCH = CHCH 2CH = CH(CH 2 ) 2 P Ph 3 I (G)
Bi 30:
a. Cng thc cu to cc cht:

b. ABA l hn hp racemic khng c tnh quang hot, c cu hnh Z, E, Z.
************************************************
Part 6 HYDROCARBON THM, DN XUT

HALOGEN, HP CHT C KIM.

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Gii thch cc d kin sau:

a. Kh nng phn ng ca chlorobenzene km benzene trong phn ng th i in t, d rng nh
hng vn u tin o-, p-.
b. Ion phenolate tham gia phn ng th i in t cc v tr o-, p-.
c. Phn ng th i in t ca acid benzoic u tin cho sn phm m-.
d. Phenol d b Br ha hn benzene.
e. Cc dn xut halogen ca hydrocarbon thm kh tham gia phn ng th i nhn hn dn xut
alkylhalogenide.
Bi 2: Ba hp cht trimethylbenzene sau, cht no c kh nng hot ha mnh nht trong phn ng th
in t SE: (1) 1,2,3trimethylbenzene ; (2) 1,2,4trimethylbenzene ; (3) 1,3,5trimethylbezene.
Bi 3: Vit cc sn phm to thnh ca cc phn ng sau y:
a. Phn ng sulfonic ha p-methylcumene. b. Phn ng sulfonic ha p-acetyltoluene.
Bi 4: Hon thnh cc phn ng chuyn ha sau:
o
a. Br(CH2)3pC6H4CH2Br
H 2 O,t

b. C6H5CH2Cl
1.KCN,DMSO
2.H + ,H O,t o

2
c. C6H5CH3
1.SO3 .H 2SO 4
2.HNO3 /H 2SO 4

3.NaOH,t o
d.
1.CH3 (CH 2 )3 Li
2.C6 H 5CHO

3.H 3O + ,t o
e.
Na 2 Cr2 O 7 / H 2SO 4

f.
1.MnO 2
2.KOH,H O,t o

2
Bi 5: T benzene hoc methylbenzene, hy vit phng trnh iu ch:

a. C6H5CH2CH2C CH. c. C6H5COpC6H4COOCH3.
b. p-ClC6H4CONH2. d. Acid 2,6dibromobenzoic.
Bi 6: Cht A c cng thc C8H6 v lm mt mu nc Br2, phn ng vi AgNO3/NH3 cho kt ta,
oxygen ha thu c acid benzoic. Xc nh cng thc cu to ca cht A.
Bi 7: Khi un nng 1,4dibromobutane vi Na2S s to thnh thiophene C4H4S. Bng phng php trn,
hy iu ch methylthiophene.
Bi 8: Trong phn ng Cl ha nh cht xc tc FeCl3, kh nng phn ng tng i ti cc v tr khc
nhau trong cc phn t biphenyl v benzene nh sau:

a. Trnh by c ch phn ng Cl ha biphenyl theo hng u tin nht.

b. Tc mono-Cl ha biphenyl v benzene hn km nhau bao nhiu ln.
c. Trong mt phn ng mono-Cl ha biphenyl thu c 10 grams 2chlorobiphenyl th s thu c
bao nhiu grams 4chlorobiphenyl.
Bi 9: Hon thnh cc chui phn ng sau:
+
a. CH3CHOHCH 3
SO 2 Cl
(A)
KCN
(B)
H 3O
(C).
CH 2 = CH 2
b. I(CH 2 ) 4 I
KCN / alcohol
(A) (B).
Bi 10: Vit phng trnh phn ng ca ethylmagnesiumbromide vi cc cht sau:
a. CH3CH2CN.
b. CH3COCl.
c. C2H5CHCH3C CH.
d. CH3COOC2H5.
e. C2H5COCH3.
Bi 11: Cho bit sn phm ca cc phn ng sau:
Bi 12: Indene C9H8 c tch t nha than , c phn ng vi KMnO4 v lm mt mu Br2/CCl4. Tin
hnh hydro ha xc tc trong iu kin m du s nhn c indan C9H10 v trong iu kin mnh hn th
c C9H16. Khi oxygen ha indene c acid phthalic. Azulene
a. Xc nh indene, indan, C9H16 v vit cc phng trnh phn ng xy ra.

b. T indene, hy iu ch azulene C16H26O.
Bi 13: Cho cumene tc dng vi CH3Cl/AlCl3 thu c cc sn phm monomethyl ha trong c A.
Khi cho A tc dng vi KMnO4 un nng thu c cht B c cng thc C8H4O4K2. Cho A tc dng vi
Br2 (xc tc bt Fe) thu c hai sn phm mono-Br C v D. Vit cng thc cu to, gi tn A, B, C, D
v hon thnh cc phng trnh phn ng minh ha.

Bi 14: Cho cetone (I) C5H10O tc dng vi ethylmagnesiumbromide ri tch nc hp cht carbonyl to
thnh thu c alkene (II), cht ny ozone ha ri thy phn cho diethycetone v acetaldehyde. Vit
cu trc ca cc hp cht (I), (II).
Bi 15: Vit phng trnh phn ng ca isobutylchloride vi:
a. AgOH. f. Na kim loi trong hexane.
b. H2O (khi un si). g. Mg trong ether khan.
c. KOH/C2H5OH. h. CH3COONa.
+
d. 1. KCN ; 2. H3O . i. KHS.
e. NH3 (un trong ng hn kn).
Bi 16: Methyl ether ca p-cresol (A) c cha O18 l mt hp cht qu khng may b trn ln vi
iodobenzene. Hy dng phng php thun tin nht c th tch ring hai cht trn. Bit nhit si
ca hai cht gn bng nhau v lng cht qu t nn khng th dng phng php sc k iu ch.
Bi 17: Cht A c cng thc phn t l C9H14. Khi oxygen ha bng K2Cr2O7/H2SO4 ta thu c
cetodiacid X mch thng (c t hn A mt carbon), A cng hp H2 to ra n-propylcyclohexane. A phn
ng vi KMnO4 long thu c Y (190 g/mol) c cng s carbon vi A. Y phn ng vi CH3COOH xc
tc H2SO4 ch to cht Z (C15H24O7). Vit phng trnh phn ng, xc nh A.
Bi 18: Tm cc cht A, B, C, D, E, F v vit cc phng trnh phn ng xy ra theo s sau:
Na2Cr2O4
C
2[ H ]
D
Benzen
Cl2 ,1mol
A
H 2O
t o ,P
B
FeCl 3
E
Fe / HCl
F
HNO3 1:1
(1 mol)
Bi 19: Oxygen ho hydrocarbon thm A (C8H10) bng oxygen c xc tc cobalt acetate cho sn phm B.
Cht B c th tham gia phn ng: vi dung dch NaHCO3 gii phng kh CO2 ; vi ethanol (d) to thnh
D ; un nng B vi dung dch NH3 to thnh E. Thy phn E to thnh G, un nng G nhit khong
160oC to thnh F. Mt khc, khi cho B phn ng vi kh NH3 (d) cng to thnh F. Hy vit cc cng
thc cu to ca A, B, D, G, E v F.
Bi 20: 3iodo2,2dimethylbutane khi phn ng vi AgNO3 trong C2H5OH s cho 3 sn phm. Vit
cng thc cu to ca 3 sn phm y v cho bit sn phm no chim t l ln nht.
Bi 21: m-Fluorisopropylbenzene (I) c tng hp theo 8 bc i t benzene (A). Hy hon thin s
phn ng ny:
o
A
+Me2 CHBr/AlCl3
B
+Br2 /Fe
C
HNO3
D
6[H]
E
HNO2
HBF4
F
t
G
Mg
H
H 2O
I
Bi 22: Xut pht t Bromobenzene cha C14 v tr 1 v cc cht v c cn thit khng cha C14, hy
iu ch cc hp cht thm cha C14 v tr 3.
a. Aniline. c. Acid benzoic.
b. Iodobenzene.

Bi 23: Ephedrine (G) l mt hot cht dng lm thuc cha bnh v h hp c chit t cy ma hong.

D 3 22 E F CH
G
CH CH NO , OH H 2 / Ni 3 Br
Ephedrine c tng hp nh sau: C6H6 CO
, HCl
/AlCl3
a. Vit cng thc cu to ca D, E, F v G trong s trn.

b. Vit c ch phn ng ca cc giai on to thnh D v E.
c. i t benzene, acid propanoic v cc tc nhn cn thit khc, hy a ra mt s tng hp
ephedrine.
Bi 24: Vit cng thc cu to sn phm cui (nu c) ca cc phn ng sau:
Bi 25: Vit cc phn ng tng hp sn phm t cc cht ban u cho di y:
************************************************
Part 6 HNG DN GII

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Bi 1:
a. Do nguyn t Cl c hiu ng +C.
b. Do nh hng y in t ca O, cng hng lm cho cc v tr o-, p- c th mang in tch m
(cng thc gii hn).
c. Do nh hng ht in t ca nhm CHO lm cho v tr o-, p- c th mang in tch dng (cng
thc gii hn).
d. Do hiu ng +C ca nhm OH.
e. Do nguyn t Cl c hiu ng +C.
Bi 2: (3) > (2) > (1).
Bi 3: Vit cc sn phm to thnh:
Bi 4:
a. Br(CH2)3pC6H4CH2OH.
b. C6H5CH2OH.
Bi 5:
1.CH3CH 2 Cl / AlCl3
2.Br2 ,t o
a. C6H6 C6H5CH2CH2C CH.
3.(CH3 )3 COOK
4.HBr,ROOR
5.HC CLi
1.Cl2 / FeCl3
b. C6H5CH3 2.Na 2 Cr2 O7
3.SOCl2
p-ClC6H4CONH2.
4.NH 3
1.KMnO 4 / OH
c. C6H5CH3
C6H5COpC6H4COOCH3.
2.SOCl2
3.C6 H5 CH 3 /AlCl3
4.Na 2 Cr2 O7
5.CH 3OH/H 2SO 4
1.SO3 ,H 2SO 4
d. C6H5CH3 Acid 2,6dibromobenzoic.
2.Br2 ,FeBr3
3.H 2 O,t o
4.Na 2 Cr2 O7 / H 2SO 4
Bi 6: Cng thc cu to ca A l: C6H5 C CH .

Bi 7: CH 2 = CHCH 2 CH 2OH
HBr
CH 3 CHBr CH 2 CH 2 CH 2 Br
Na 2S
Metylthiophene .

Bi 8:
Bi 9: Hon thnh cc chui phn ng:

+
a. CH3CHOHCH 3
SO 2 Cl
CH3CHClCH 3
KCN
CH 3CHCNCH3
H 3O
CH3CHCOOHCH 3 .
CH 2 = CH 2
b. I(CH 2 )4 I
KCN / alcohol
CH 2 = CH CH = CH 2 cyclohexene.
Bi 10:
a. CH3CH2COCH2CH3.
b. CH3COCH2CH3.
c. C2H5CHCH3C CMgBr + C2H6
d. CH3COOC2H5.
e. (C2H5)2C(OH)CH3.
Bi 11: Cho bit san phm ca cc phn ng:
Bi 12:
a. Cng thc cu to:

b. iu ch:
Bi 13: A l p-methylcumene. Cc phn ng:

o
A + 8KMnO4
t
p-KOOCC6H4COOK (B) + 2K2CO3 + 8MnO2 + 2KOH + 4H20.
+ Br2 (Fe)
A
HBr
C+D
Trong : C l o-Bromo-p-methylcumene. D l m-Bromo-p-methylcumene.
Bi 14: Cng thc cu to cc cht: (I) l diethylcetone. (II) l 3ethylpent2ene.
Bi 15:
a. CH3CHCH3CH2OH. f. CH3CHCH3CH2CH2CHCH3CH3.
b. CH3CHCH3CH2OH. g. CH3CHCH3CH2MgCl.
c. CH3CHCH3=CH2. h. CH3CHCH3CH2OCOCH3.
d. CH3CHCH3CH2COOH. i. CH3CHCH3CH2SH.
e. CH3CHCH3CH2NH2.
Bi 16: Ha tan hn hp trong ether v thm mt lng Mg va , khi iodobezene chuyn thnh
phenylmagnesiumiodide. Thm nc vo hn hp sau phn ng, khi phenylmagnesiumiodide c th
chuyn thnh benzene trong khi methyl ether ca p-cresol khng thay i. Hn hp lc ny gm c
Benzene ( t so = 80o C ) v methyl ether ca p-cresol ( t so = 175o C ) c th phn tch d dng bng phng
php chng ct.
Bi 17:
- T d kin A cng hp H2 n-propylcyclohexane v oxygen ha bng K2Cr2O7/H2SO4 ta thu
c cetodiacid X mch thng (t hn A mt carbon) => A c t nht mt lin kt i u mch.
- V X l cetodiacid => A c 2 lin kt i hoc 1 ni i trong vng v phi c nhm:
C C = CH C
C
- A phn ng vi KMnO4 long thu c Y (190 g/mol) c cng s carbon vi A => s nhm OH
trong Y l (MY MA)/17 = 4 => CTPT ca Y l C9H14(OH)4.
- Y phn ng vi CH3COOH xc tc H2SO4 ch to cht Z (C15H24O7) => Z c 3 nhm ester ca
acid acetic v trong phn t cn 1 nhm OH khng to ester. Nhm OH lin kt vi C (III).

- Vy cng thc cu to ca A l:
- Vit cc phng trnh phn ng da vo A l hp cht va tm c trn.

Bi 18: Hon thnh s phn ng:
A l chlorobezene. D l hydroquinone.
B l phenol. E l p-nitrophenol.
C l p-benzoquinone. F l p-aminophenol.
Bi 19: Cng thc cu to ca cc cht:
CH3 O
C
CH3 O
C
O
A B
O O
C C OC2H5
O + C2H5OH
C C OC2H5
O D O
O O
C C
O + NH3 (kh, d- ) N H
C C
O O ftalimit F
O O
C NH2 160OC C
N H
C OH C
G O F O
Bi 20: (CH3)3CCHICH3 + Ag+ (CH3)3CC+HCH3 + AgI.

- (CH3)3CC+HCH3
C2 H5 OH
(CH3)3CCH=CH2 (A).
- (CH3)3CC+HCH3 (chuyn v CH3) CH3C+CH3CH(CH3)2
C2 H5 OH
(CH3)2CH=CH(CH3)2
Sn phm (B) l chnh.
- CH3C+CH3CH(CH3)2
C2 H5 OH
CH2=C(CH3)CH(CH3)2 (C).
Bi 21: Hon thnh s phn ng:
A l benzene. E l p-bromo-m-aminocumene.
B l cumene. F l p-Br-m-+N2BF4C6H3CH(CH3)2.
C l p-bromocumene. G l p-bromo-m-fluorcumene.
D l p-bromo-m-nitrocumene. H l m-fluor-p-magnesiumbromocumene.
Bi 22: S tng hp
a. Aniline:

b. Iodobenzene:
c. Acid benzoic:
Bi 23:
a. Tng hp ephedrine:
b. C ch phn ng:
C ch phn ng to thnh D: phn ng th electrophile vo nhn thm, SE:
C ch phn ng to thnh E: phn ng cng nucleophile vo nhm carbonyl, AN:
c. S tng hp khc i t acid propanoic v cc tc nhn cn thit khc:

Bi 24: Vit cng thc cu to sn phm cui (nu c) ca cc phn ng:
Bi 25: Vit cc phn ng tng hp:
************************************************

Part 7 ALCOHOL PHENOL

ALDEHYDE CETONE
-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Cho cc alcohol: (1) p-CH3-C6H4-CH2OH , (2) p-CH3O-C6H4-CH2OH, (3) p-CN-C6H4-CH2OH v

(4) p-Cl-C6H4-CH2OH. So snh kh nng phn ng ca cc alcohol trn vi HBr v gii thch.
Bi 2: Cho s cc phn ng sau:
OH
HCHO H2O O Cl
A NaCN B C D1 + D2 + E (sn phm ph)
OH - DMF
Hy vit cng thc cu to ca A, B, C, D1, D2 v E. Bit E c cng thc phn t C19H22O5N2.

Bi 3: Hp cht A (C4H6O3) quang hot, khng tham gia phn ng trng bc, tc dng vi anhydride
acetic to ra dn xut monoacetate. Khi un nng vi methanol, A chuyn thnh cht B (C5H10O4). Di
tc dng ca acid v c long, B cho methanol v C (C4H8O4). C tc dng vi anhydride acetic to ra dn
xut triacetate, tc dng vi NaBH4 to ra D (C4H10O4) khng quang hot. C tham gia phn ng trng bc
to thnh acid carboxylic E (C4H8O5). X l amide ca E bng dung dch long sodium hypochlorite to ra
D-(+)-glyceraldehyde (C3H6O3) v ammonia.
Bi 4: Vit cng thc cu to cc sn phm hu c A, B, C v D trong s sau:
O
CH2 C
NBr
CH2 C
1. Li
HBr 2. CuI O N H /O
Cyclohexanol A B (NBS) C 2 4 2 D KOH
3. Br C2H5OH
Bi 5: Xc nh cc cht t A n G v hon thnh cc phng trnh phn ng trong chui bin ha sau:
o o

1.CH3 MgCl
2.H O +
C6 H12 O( A)
H 2SO 4 ,t
C6 H10 (B)
H 2SO4 ,t
C6 H12 O(D)
3
KMnO (c nng) H Pt 1. CH MgCl

4 / 2 3
C10H16 (G) Methyl cyclopentane 2. H3O+
H2SO4 (un nng)

C10H18O (F)
1.Mg ,ether
2.Cyclopentanone
C 5 H 9 Br( E )
HBr

C6 H 5COOOH
C5H8O (C)
+
3.H 3 O
Bi 6: Thc hin dy chuyn ha sau:
HS (CH 2 )3 SH
PhCHO
H+
A 1.BuLi
2.Ethyl trans But 2 enoate
B
+ o
Ni,Raney
H2
C
H 2SO4
H2 O
D
H ,t
E

Bi 7: T nha thng, ngi ta tch c cht hu c (X) v chuyn ha (X) theo s sau:
Bit A c cng thc phn t l C9H14O.

a. Vit cng thc cu to cc sn phm hu c A, B, C1, C2, C3, D, E.
b. Sn phm no c to thnh ng phn v ch r s lng ng phn ca mi sn phm.
Bi 8: Hp cht hu c A cha 79,59 % C ; 12,25 % H ; cn li l O ch chim mt nguyn t trong phn
t. Ozone phn A thu c HOCH2CH=O ; CH3[CH2]2COCH3 v CH3CH2CO[CH2]2CH=O. Nu cho A
tc dng vi Br2 theo t l mol 1:1 ri mi ozone phn sn phm chnh sinh ra th ch thu c hai sn
phm hu c, trong c mt cetone. un nng A vi dung dch acid d dng thu c sn phm B c
cng cng thc phn t nh A, song khi ozone phn B ch cho mt sn phm hu c duy nht.
a. Xc nh cng thc cu to v gi tn A.
b. Tm cng thc cu to ca B v vit c ch chuyn A thnh B.
Bi 9: Vit cc phng trnh phn ng theo s sau:
+X
C (ethylene glycol diacetate)
o Trng ngng
2HCHO
P,t ,xt
A
H 2 ,xt
B D (poliether)
o
+ CuO, t Ca (OH )
E
O2 ,xt
F (acid a chc)
2(d )
G
Bi 10: Khi cho cis v trans-3,3-imethyl-2-bromocyclohexanol phn ng nhanh vi base mnh s thu
c 2 sn phm ring bit. Sn phm to thnh t cis-bromoalcohol c vn hp th 1710 cm-1, cn sn
phm kia khng c vn hp th ny v cng khng c vn hp th 3350 cm-1. Xc nh cng thc cu
to ca cc sn phm trn.
Bi 11: Hp cht A phn ng vi PCl3 cho ra B, kh ha B bng H2/Pd nhn c benzaldehyde. Mt
khc cho B tc dng vi NH3 c C, x l C vi Br2 trong mi trng kim c D. T B c th nhn
c E bng cch cho phn ng vi benzene xc tc AlCl3. E chuyn thnh F khi x l vi
hydroxylamine, trong mi trng acid F chuyn thnh G. Vit cng thc cu trc cc hp cht trn.
Bi 12: Vit cng thc cu trc ca cc sn phm trung gian v dng mi tn ch r s tng tc ca
nhn vi trung tm phn ng:
+
OEt
X
OEt
A
ph vng
B
HOEt
C
OEt
D
khp vng
E F
OEt
G
H
Y
Trong X, Y ln lt l:
(X) (Y)

Bi 13: Tin hnh ngng t gia benzaldehyde v ethyl methyl cetone ln lt trong mi trng acid v
mi trng base ngi ta thu c 2 sn phm khc nhau. Vit CTCT cc sn phm to thnh, gii thch.
Bi 14: Hp cht A C4H8O3 quang hot, tan tt trong nc to thnh dung dch phn ng acid vi giy
qu. un mnh dung dch, A chuyn thnh cht B C4H6O2 khng quang hot tan va phi trong nc v
cng cho phn ng acid vi giy qu. B phn ng vi KMnO4 mnh lin hn A. Oxygen ha A bng
dung dch H2CrO4 long s thnh cht lng bay hi C C3H6O. C khng phn ng vi KMnO4 nhng cho
phn ng vi I2 trong dung dch kim. Vit CTCT cc cht v phng trnh phn ng xy ra. Cc d kin
trn iu kin xc nh cu trc ca A cha, gii thch.
Bi 15: Hp cht hu c A c cng thc C17H30O b oxygen ha nh cho 2 acid l: acid octandioic v
acid nonandioic. Hy gi tn A theo danh php IUPAC v chuyn hn hp ng phn ca n thnh cis-A.
Bi 16: Hp cht X C6H9OBr phn ng vi methanol trong mi trng acid sinh ra Y C8H15O2Br. Cho Y
phn ng vi Mg trong ether khan, sau cho phn ng tip vi aldehyde formic c cht E. Thy phn
E trong mi trng acid c F, dehydrate ha F thu c 2-vinylcyclopentanone
a. Xc nh CTCT ca X
b. Nu mun iu ch F t X c nht thit phi qua cc giai on nh trn khng, v sao.
Bi 17: C 5 l khng nhn c k hiu t A n E cha ring l 5 hp cht thm sau:
C6H5COCH2CH3, C6H5COOH, C6H5COCH3, C6H5CH(OH)CH3 v C6H5CHO. Da vo cc kt qu th
nghim sau y nhn bit ha cht c trong mi l:
Cho vo mi l 1 git dung dch K2Cr2O7/H2SO4 ri lc u. Sau vi pht thy l A v C bin i
dung dch mu da cam thnh xanh lc.
Cho vo mi cht mt t dung dch NaOH long th ch ring l B tan c.
Khi cho tc dng vi I2 trong dung dch kim th l A v E cho kt ta vng.
L C, D v E u tc dng vi 2,4-dinitrophenylhydrazine cho kt ta , da cam.
Bi 18: C 4 hp cht thm: C6H5OH ; C6H6 ; C6H5CH3 ; C6H5NO2. Xt bng sau:
Cht phn ng A B C D
Nc Br2 Khng phn ng C phn ng Khng phn ng Khng phn ng
Phn ng 0o C v Ch phn ng khi
Br2/Fe C phn ng C phn ng
khng cn xc tc Fe un nng
Phn ng vi c dung Ch phn ng khi C phn ng
HNO3/H2SO4 C phn ng
dch HNO3 long un nng khng cn H2SO4
a. Xc nh k hiu A, B, C, D cho mi cht.
b. Hy sp xp cc cht theo th t tng dn v kh nng tham gia phn ng th vng benzene.
Gii thch s nh hng ca cc nhm th n kh nng .
Bi 19: T ht tiu ngi ta tch c hp cht A (C17H19NO3) l cht trung tnh. Ozone phn A thu
c cc hp cht: ethadial, B, D. Thu phn B thu c OHC-COOH v hp cht d vng 6 cnh
piperidine (C5H11N). Cho D tc dng vi dung dch HI c thu c 3,4-dihydroxybenzaldehyde. Hy
xc nh cng thc cu to ca A, B, D v cho bit c bao nhiu ng phn lp th ca A.

Bi 20: T cc cht ban u c s nguyn t carbon 3, vit cc phng trnh phn ng (ghi r iu kin
nu c) iu ch: Acid cyclobutanecarboxylic v Cyclopentanone.
************************************************
Part 7 HNG DN GII

-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
Bi 1: Phn ng gia cc alcohol cho vi HBr l phn ng th theo c ch SN. Giai on trung gian
to carbocation benzylic. Nhm OCH3 y electron (+C) lm bn ho carbocation ny nn kh nng
phn ng tng. Nhm CH3 c (+I) nn cng lm bn ha carbocation ny nhng km hn nhm OCH3
v (+C) > (+I) . Cc nhm Cl (-I > +C) v CN (-C) ht electron lm carbocation tr nn km bn do
vy kh nng phn ng gim, nhm CN ht electron mnh hn nhm Cl.
Vy sp xp theo trt t tng dn kh nng phn ng vi HBr l:
p-CN-C6H4-CH2OH < p-Cl-C6H4-CH2OH < p-CH3-C6H4-CH2OH < p-CH3O-C6H4-CH2OH.
Bi 2: S iu ch p-hydroxyphenylacetamide
CH2OH CH2CN CH2CONH2
HCHO NaCN H2O
-
OH DMF
HO HO HO HO
A B C
OH OH
O O Cl
O Cl O +
H2NCOCH2
H2NCOCH2 H2NCOCH2
C D1 D2
Sn phm ph:
OH
O O
C19H22O5N2
H2NCOCH2 CH2CONH2
Bi 3: S chuyn ha gia cc cht:
CHO COOH CHO
H OH
CH2OH CH2OH CH2OH

H
D-Glyxeraldehit E eO
D-Glyceraldehyde M C
MeO
O CH2OH
O MeOH
O
CH2 CH2 CH2OH

A B D

Bi 4: Cng thc cu to cc sn phm:
Bi 5: Cng thc cu to cc cht trong s :
Bi 6: Cng thc cu to cc cht trong s :

Bi 7:
a. Cng thc cu to sn phm:
b. Cc sn phm to thnh c ng phn:

- C3 c 2 ng phn quang hc
- C2 c 4 ng phn quang hc
- D c ng phn E, Z.
Bi 8:
79, 59 12, 25 8,16
= = = 13 : 24 :1 => A c cng thc phn t l C13H24O
12 1 16
T sn phm ozone phn, tm ra 2 cng thc cu to c th ph hp:
T sn phm Br ha ri ozone phn => A1 ph hp v:
Tn ca A: 3-Ethyl-7-methyldeca-2,6-diene-1-ol

b. B phi l hp cht mch vng cha mt ni i trong vng, B sinh ra t A do phn ng ng vng
Bi 9:
o
2HCHO
p,t ,xt
HOCH 2 CHO ( A).
HOCH 2 CHO + H 2
xt
HOCH 2 CH 2 OH (B).
2CH 3COOH + C2 H 4 (OH)2
(CH3COO)2 C2 H 4 (C).
HOCH 2 CH 2 OH
trng ngung
(OCH 2 CH 2 )n (D) + nH 2 O.
o
HOCH 2 CH 2 OH + 2CuO
t
OHC CHO (E) + 2H 2O+2Cu.
OHC CHO + O 2
xt
HOOC COOH (F).
HOOC COOH + Ca(OH) 2
CaC2 O 4 (G ) + 2H 2O.
Bi 10:
- trans-3,3-imethyl-2-bromocyclohexanol khng b tch HBr m c th phn ng SN2 ni phn t
- cis-3,3-imethyl-2-bromocyclohexanol tch HBr to enol khng bn chuyn thnh cetone (h bin

ceto-enol) c vn hp th 1710cm1.
Bi 11:
- A l PhCOOH. - E l PhCOPh.
- B l PhCOCl. - F l Ph2C=NOH
- C l PhCONH2. - G l PhCONHPh.
- D l PhNH2 (+CO2). (F G chuyn v Beckman)

Bi 12: Vit cng thc cu trc ca cc sn phm trung gian v dng mi tn ch r s tng tc ca
nhn vi trung tm phn ng:
Bi 13:

- Trong mi trng base: C6 H 5CHO + CH3COCH 2 CH 3
OH
to
C6 H5CH = CHCOCH 2 CH 3 + H 2O .
H ca CH3 c tnh acid mnh hn H ca CH2.

+
- Trong mi trng acid: C6 H 5CHO + CH3COCH 2CH 3
H
to
C6 H 5CH = C(CH3 ) COCH 3 + H 2O.
Khi c xc tc acid, cetone s b enol ha m CH3=C(OH)CHCH3 bn hn.

Bi 14:
- C l acetone CH3COCH3.
- A l CH3CHOHCH2COOH.
- B l CH3CH=CHCOOH (cis/trans).
- iu kin xc nh A v ch c cetoacid th nhm COOH mi d b decarboxyl ha
v vy A ch c th l acid 3hydroxybutanoic thay v acid 2hyroxybutanoic.
Bi 15:
Vy A l cycloheptadex9enone.

Chuyn hn hp cc ng phn v cis:

1.Br2 / 20o C
2.C2 H 4 (OH)2 / H +
A(transv cis)
cis A
3.KOH / C2 H5 OH
4.H 2 ,Ni / C 2 H5 OH
5.H 3 O +
Bi 16:
a. Cht Y cha nhiu hn X 2 nguyn t carbon, 6 nguyn t hydro v 1 nguyn t oxygen, suy ra X
phn ng vi 2 CH3OH v tch loi 1 phn t H2O dn n s hnh thnh acetal methylic t X.
Cht F sau khi dehydrate ha to ra 2vinylcyclopentanone. Vy F phi c cng thc cu to l:
b. Khi iu ch nht thit phi qua cc giai on trn v nu khng qua giai on to Y th hp cht
c magnesium s phn ng vi nhm C=O. Nu a 1 C qua phn ng vi KCN th nhm C=O
cng c th phn ng vi KCN.
Bi 17:
- A l C6H5CHOHCH3
- B l C6H5COOH
- C l C6H5CHO
- D l C6H5COC2H5
- E l C6H5COCH3
Bi 18:
a. A l C6H6 ; B l C6H5OH ; C l C6H5NO2 ; D l C6H5CH3
b. Kh nang phn ng th vng benzene tng dn theo th t: C < A < D < B
Gii thich:
- Phn ng th H vng benzene theo c ch SE.
- Tc nhn electrophile tn cng vo electron ca nhn thm. Do o nguyn t hay nhm nguyn
t no lm tng mt electron ca nhn benzene (nht l v tr ortho-, para-) phn ng cng d
dng.
- Ly C6H6 lm mc so snh, ta thy nhm CH3 c hiu ng +I v nhm OH c nhm +C y
electron mnh hn nhm CH3. Hai nhm ny lm tng mt electron ca nhn thm ti cc v tr
ortho-, para-. V vy ta c phn ng th ca B > D > A.
- Nhm NO2 c hiu ng I, C ht electron mnh v lm gim mt electron ca nhn thm,
lm gim kh nng phn ng th H vng benzene so vi C6H6 => C < A.

Bi 19: Ozone phn A thu c ethadial chng t trong A c nhm =CHCH= . Thu phn B thu c
OHC-COOH v piperidine, suy ra B c lin kt O=CN v N nm trong vng 6 cnh. D phn ng vi
HI thu c 3,4-dihydroxybenzaldehyde. Vy c cc cng thc cu to:
Trong A c 2 lin kt i, s ng phn hnh hc l 4: ZZ , EE , ZE , EZ.

Bi 20: S iu ch:
************************************************

TI LIU THAM KHO:
1. Bi tp L thuyt v Thc nghim, tp 2: Ha Hc Hu C Cao C Gic NXB Gio Dc 2006.

2. Bi tp Ha Hu C Trn Th Vit Hoa, Trn Vn Thnh NXB i Hc Quc Gia TP H Ch
Minh 2003.
3. B thi HSG Quc gia lp 12 THPT.
4. B thi Olympic 30/4 cc tnh pha nam.
5. Bi tp Ha Hu C, tp 1 Ng Th Thun NXB i hc Quc Gia H Ni 1999.
6. Bi tp Ha Hu C, tp 2 Ng Th Thun NXB Khoa hc v K thut 2008.
7. Bi tp Ha Hu C i Hc Y Dc TP H Ch Minh 2001.
8. Tng hp Hu C Nguyn Minh Tho. NXB i hc Quc Gia H Ni 2001.
9. Mt s cu hi v bi tp Ho hu c - o Vn ch, Triu Qu Hng - NXB i Hc Quc Gia
H Ni.

************************************************
LI M U
Phn 1: HIU NG HA HC
BI TP ......................................................................................................................................Trang 1
P N .......................................................................................................................................Trang 3
Phn 2: NG PHN
BI TP ......................................................................................................................................Trang 7
P N .......................................................................................................................................Trang 10
Phn 3: C CH PHN NG
BI TP ......................................................................................................................................Trang 15
P N .......................................................................................................................................Trang 19
Phn 4: ALKANE CYCLOALKANE
BI TP ......................................................................................................................................Trang 26
P N .......................................................................................................................................Trang 28
Phn 5: ALKENE ALKINE DIENE TERPENE
BI TP ......................................................................................................................................Trang 34
P N .......................................................................................................................................Trang 39
Phn 6: HYDROCARBON THM DN XUT HALOGEN HP CHT C KIM
BI TP ......................................................................................................................................Trang 49
P N .......................................................................................................................................Trang 53
Phn 7: ALCOHOL PHENOL ALDEHYDE CETONE
BI TP ......................................................................................................................................Trang 58
P N .......................................................................................................................................Trang 61
TI LIU THAM KHO ......................................................................................................Trang 64

MC LC ...................................................................................................................................Trang 65
- - - - - - - - - - Ht tp 1 - - - - - - - - - -

BT Hoa Huu Co

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

BT Hoa Huu Co

Uploaded by

Copyright:

Available Formats

volcmttl@yahoo.com.

Ti liu dnh cho:

(1) (2) (3) (4) (5)

(1) (2) (3) (4) (5)

Copyright 2009 volcmttl@yahoo.com.vn 1

115oC 117oC 256oC 187oC

(1) acid iso-Crotonic (2) acid Crotonic

Copyright 2009 volcmttl@yahoo.com.vn 2

Bi 20: Xc nh tm base mnh nht trong cc alkaloid sau:

Part: 1 HNG DN GII

c. Cng thc gii hn ca (c)

d. Cng thc gii hn ca (d)

Copyright 2009 volcmttl@yahoo.com.vn 3

Copyright 2009 volcmttl@yahoo.com.vn 4

- Ngoi hiu ng I cn c thm hiu ng +C lm gim di lin kt CCl

(1) 240oC (2) 273oC (3) 285oC

H COOH - H+ H COO- - H+ H COO-

Copyright 2009 volcmttl@yahoo.com.vn 5

- k1(M) > k1(F) l do M c kh nng to lin kt hydro ni phn t, lin kt OH ca M trong qu

Copyright 2009 volcmttl@yahoo.com.vn 6

Bi 1: Vit cc ng phn cu to ca cc cht sau:

Bi 2: Cht no sau y c ng phn hnh hc, gi tn cc ng phn theo danh php Z, E.

(a) (b) (c)

Bi 6: Vit cng thc chiu Newman dng bn ca:

Copyright 2009 volcmttl@yahoo.com.vn 7

Serine Adrenaline (Corticoid) Menthone

H2O18 nh sau: RCOOR + H2O18

Copyright 2009 volcmttl@yahoo.com.vn 8

Da vo cc kt qu trn, hy gii thch s thay i du nng sut quay cc [ ]D ca alcohol ban u

Bi 14: Quang ph hp th in t ca formaldehyde c ba cc i 295 nm, 185 nm v 155 nm. Nu

Bi 17: Khung carbon ca cc hp cht terpene

Bi 18: Vit cng thc Fischer ca cc cht C v D trong dy chuyn ha sau:

Bi 19: Vit cng thc chiu Fischer cc ng phn lp th ca acid 2bromo3methylsuccinic v ch ra

Copyright 2009 volcmttl@yahoo.com.vn 9

a. Hy so snh tnh acid ca A v B.

Part 2 HNG DN GII

- i c hai ng phn hnh hc do vng cyclopropane phng (mt c nh).

Copyright 2009 volcmttl@yahoo.com.vn 10

(a) (b) (c)

b. (B) c 1 dng bn:

c. (C) c 1 dng bn:

Copyright 2009 volcmttl@yahoo.com.vn 11

b. (CH3)2CHN=O. H bin nitro-axi

Bi 11: Xc nh cu hnh ca A, B (dng cis, trans) v vit cu dng gh tng ng

Copyright 2009 volcmttl@yahoo.com.vn 12

- Cu trc ca (E) l: Cu trc ca (F) l:

b. ng phn quang hc:

Copyright 2009 volcmttl@yahoo.com.vn 8

Bi 14: Ba cc i hp th 295 nm, 185 nm v 155 nm tng ng vi s chuyn di in t mc nng

Bi 17: Acoron v acid abietic l terpene

Bi 18: Cng thc Fischer ca cc hp cht C, D

Copyright 2009 volcmttl@yahoo.com.vn 13

(I) (II) (III) (IV)

Bi 20: So snh, gii thch

Copyright 2009 volcmttl@yahoo.com.vn 14

Bi 1: Cho bit cc phn ng sau xy ra theo c ch g. Vit c ch phn ng.

b. CH3CH2Cl + KCN h. Pyridine + C2H5I

b. Hon thnh s sau:

c. Hon thnh s sau:

Bi 3: Cho bit sn phm to thnh trong cc phn ng sau, nu c ch phn ng

Copyright 2009 volcmttl@yahoo.com.vn 15

Bi 4: So snh kh nng phn ng ca cc cp cht sau:

Bi 6: Cho s phn ng: