HC=CH —"¥CH,=CH, — CH,CH,Br —
°e
Na Ale
“+ CH,CH,CH,CH, —? CH, Gii-Ch =
CH, 80%
clang sie ki
= CH\CH,CH,CH, — H,-CH-CH,
‘20% dé tach city
20 ~ G10.
©) CO + Hy 22 CH,OH CHI
300°C.300aIm_
4,0 Na trong cH,t
Cal, HC=CH HC=CNa CH;-
> Nay ling
Fels oly Hor
= CH,-CH=CH, CICH,-CH=CH)
ry . 00°C peoxit
— cicH,-cH,-cH,-Br "+ cH,—cH,
‘A
2
2.11. a) 2,5-dimetylhexan; isopropylisobutylmetan
b} 2,2,4—trimetylpentan; isopropyltert—butylmetan.
©) 2,4—dimetylhexan; isopropylsec-butylmetan,
4) 4,4—di—n—propylheptan; tetra—n—propylmetan.
¢) 8~metylpentan; dietylmetylmetan
f) 2-metyl—S—isobutylnonan; n—bulylisobutylisoamylmetan;
n—butylisobutyl—(2—metylpropylmetan
2.12. 1) CHy-CH,-CH;~CH-CH,-CH~CH,
CICHS)3
Br CH,
b) CH,-CH,-UH-CH-6-CH,-CH,-CHy
a bcny,
c) CH,CI-CH,-CH)-CH~CH)~CH)-CH,Cl
€H,-CHCI
2.13. 4) 2C,H,, + 190; 12C0, + 14T1,0
b) 2CH,-CH-CH, + 2Na—~ CH,-CH-CHI-CH, + 2NaBr
L I
Br CH; CH, 82 Ankan
500°C.
©) CHy + HNO, EV cHANO, + H,0
@) C,H,Mgl + H,0 + CH,-CH, + Me
a mon £m
6) CH;-C-CH,CI + Hj CH;—C-CH, + HCL
CH, cH,
2.14, 61,92¢
2.15, 40,9¢
4H
2.16. a) CH3~CO-CH(CH,),
: CH,CH,CH(CH,), + H,0
Phan Ung Clemmensen ~
b) Phan ung Kisnhe — Vonfy (qua hidrazon trung gian)
(CH,),CH-C=0 + H,N-NH, > (CH,),CH-C=N-NH,—>
| 1
CH, CH,
RO
——+ (CH;),CH-CH,-CH, + N,
" #61
©) CH,COCH(CHs); == | CH,CHOH-CH(CHs) — CH,CHCICH (CHS), +
jaro
Mt HOH
—S CH CHUMgCNCH(CH,)) > CHCH,CHICH,), + 12Mg(OH), + 1/2M gO),
ele khan
KOH HBr
2.17, CH,-CH-CH,—CH,Cl — CH,-CH-CH=CH;
ancol
1
CH, cH,
Na
— CH;-CH-CHBr -CH)—= CH,—GH—-GH-CH-CH-CH,
CH; Hy CH; CH; CH,
600°C
2.18, CH,-CH,-CH, ——= CH,~CH=CH, + CH,=CH,
HBr 14,50,n,0°
CH,-CHBr-CH, CH,-CH,OH
Mg Cu 325°C
CH,~CH(MgBr)CH, cH,—CHO
H,0*
soc
Cl GH-GHCL —* CH,-CH-CH-cHts
CH; CH, CH; OH
Na
CHs-CH-CH-GH~CH-CH3
CH, CH, CH; CH; Hoa hoc Hou co - Phan Bai tap 83
0.
oO, Ys bét Zn
2.19. CHy—CH=CH, —+CH,-CH® CH, +) CH,CHO + HHO
0-0 °
cH,OH CH,OH
Ca(OH), Calor Pers
cx,on-c-cro 2% oy jon = 6 = cH,0n 2S
HCHO
CH,OH CH,OH
2,20, CH=CH
= "OE nO
UAH, 80,
2.21. cH,coon MS cHycH,onee. cu, -cH, % —- CH,CH,
Ho ‘ear Pp
aN cao-Naok
222./ \+ HBr > CH,CH,CH,Br CH,-CH=cH, —~
7
Her
=) cH,-cHBr-cH, CHy-CH-CH-CH,
1
CH, CH,
2.23. a8 + fon, b) HC
aC 5Xe
7 6 4
‘ "oe
Oo Ch; CH
KN
2.24. BrCH,),Br
ual,
> CH,OH(CH, ,CH,OH
NC(CH);CN COOH (CHz);COOH —
Br(CHy)sBr ———
KON #20 ©,H,0HH*
——~ cnc) CN COOH(CH,),COOH
CyHO™
——-+ €,H,00C(CH;},COOC,Hs
‘ “nigung tu Claises
225 Oat Onoitt O) 28 Cp 84 Ankan
2.25, a) Khtr héa butyl iodua
»
CH,-CH,— -CH)I + HI —————» CH,-CH)-CH,-CH i;
s CHI CH,“ CHA + HT — Se CH, CH,-CH,~CHly + 1,
it ety] iodua
2CH,-CH,I + 2Na + CH,—CH,-CH,~CH,+2Nal
¢) Phan ing Konbe: Dién phan axit propionic
ign phan
2CH,CH,COOK + 21,0:
2.26. a) 2; b) 4
b) Phan ting Vuyée:
CH,CH,CH,CH, + 2CO, + 2KOH + H,
2.27. (C,H,),Mg + CH,OH > C,H, + CH,OMgC,H,
CH,OMgC,H, + CH,OH = C,H, + (CH,O),Mg
2.28. Totranitrometan co thé phan hiy think 6 mol sAn phdm khi nén no 1a
chat né_
CINO,), > 2N, + CO, + 80,
con nitrometan khong chia di lvgng oxi dé chuyén tit ca cacbon va hidro thanh
san phdm khi, con 1 nguyén tit nito chi cd thé cho 1/2 Ny.
c4H,coot 2aitig
2.29. a) CH, c,H.CocH, “8. cH.c,H,
AIC, HI
hoae:
CH.
Neen ov, 2! 6 HC4ld
DOFN-NH;, = Cy HC Hy
3H
b) C,H,Br + BrC,H, + 2Na —+ C,H,C\H, + 2NaBr
GgH,MaBr
o
ce) C,H,CHO C,Hj;CHOHC,H, —4+ C,H\CH=CHCH,CH, +
HOH
He
> 6H sC.Hy
xt
Lia,
2.30. CH,COOH CH,CH,OH
H,0*
CHyCH,OH CgHgCH,CHO
00C-CH,cOOH— CH,CH,00C-CH,COOH— 22s
CH, oH CH, CH,
Sone e a 430° oO New
He-Coon cu oa
COOC)H, C2H.00C HoOC
ep Héa hoc Hau co - Phin Bai tap a5
2.31. a) Cl co thé 6 vi tri exo (cis) hoac endo (rans) so vdi C? celia cau ndi, dé
la cau ngén nhat
7 7
cl Lb
H cr
ero —2-lobinxiclo[22:3]heptan endo-2-clobinicla {2.21 heptan
b} Cl d C7 c6 thé 1A syn icis) hoac anti(trans) déi véi cau chia nhém thé (CH,-)
Clk HOCH
CH, chy >
H H
e10—2-metyl—sy—7— ere 2=metyl-anti~7~
clobixiclol2.2,Imeotan clobixiclo|2.2sIneptan
cl. 4 Cl
K 4
CH, CH,
endo ~2—metyl=syn—7— endo2—metyl- anit
clobixiclof2.2}heptan clobirilo[22}neptan
2.32. a) I: xiclopropan; 2: metylxiclopropan
b) 1: eacben :CH,; 2: ICH,Zal, hgp chat nay duge goi la cachenoit vi dé la
tién chit cia cacben :CIL,
¢} Phan wing cong hop déng vong,
2.83, a) :CCl, cong hyp cis vao C=C, nhung két qua la vong ba conh co thé
hoge & vi tri cis hoac trans vai nhom CH, s@ duge A va B
b) Anion CIBr,C: duge tao thanh sé mat Br- cho cacben CIBrC: ; cacben nay
cong vao C=C, Cl hoae Br sé 4 vj tri e’s vii nhém CH, (€ va D)
Br cl
Cl, Cl, oe xX, er
" CH,
A 8 c b 3. ANKEN
3.1, a) & b)
cH,
CH.
©) oo a) O
©) CHj=CH-CH-CH=CH, 1 CICH,CCI,CH,CH=CH,
CHCH,CH,
3.2. a) CH,CH=CHCH(CH,)C,H,
b) Co bon dong phan 4—metylhexen-2
or ny, 4 ois
= CA BOC RC
u7 Me Ms OH er Ny
i
1B) 4) CH, C3Hs, wei on
H H
Nee 4 Nene”
= H H ~~
cH Nb ots Cha CHy
| Cy
2s
12) 8p CoHs
Zr itt
3.3. a) H Br
Pad Hy
(CH,),CH CH, “Saat, c-er,0n,
H
c CH,CH, H
©) CH,~¢*-CH=cH ) Nod H
4~C"-CH=CH, =
| CoN
H cH, cH
|
2 CCHCH
F
3.4, Cac dong phan cia anken xuat phat ti¢ khung C khac nhau roi them néi
doi: Hoa hoc Hou co - Phin Bai 87
{
c-c-c-c-¢ c-o-c-¢ c-c-¢
1 \
c c
A B Cc
Tu A ta 06
CH: HCH. CH. A
CH,=CHCH,CH,CH, Spies cnc
penten—1 W H va H CH,CH;
}-penten-2 (E}-ponten=2
Tit B e6 ba ddng phan cu tao akung khong ed dong phan hinh hoe:
CH, =C-CH,-CH, CH,-C=CH-CH, CH,-CH-CH=CH,
I I I
CH, CH; CH,
2-metylouten=1 2-metybuten-2 a-meryibuten—1
Cacbon bac bén tit dong phan C khong thé c6 ndi doi.
3.5. a}
&
+) BH, /THF ©)
Do. ae ep
CH, +
2) Bry i are H
Ck hn,
3 iy
(2)-2.8-aldgtero— san, enthro=2 -biem ~23~dideter0— cH,
fens aian
er
er
ganar OMS + wo,
2) Bry x cH, SH
CHy” Ni
Do o c Hy
(E}-23-didotero—buten-2
rar thrcon 2—btom—2,3~didetero—butan
4) Bry THE
b 1 Bry THE
J 2 21 Br, ) + ,
a6 HBr Br H
sax. cis 12 diddterobrom
xiclohexan
3.6. a) CH,-CHBr-CH,
b) (CH,),CH-CHBr-CH,
} CH,CH,-CHOH-CH,C1
(a) THF: tetranidrofuran 88 Anken
d) CH,-CH,—080,-0H
cao
7
e) a!
0
f) CH,CH,CH,1
8) (CH,),C=CHCH,CH, + CH,OH + NaC
h) Xiclohexen + HO
3.7. a) + HI
b) oxi hda bing KMnO,/kigm
©) + HBr va peoxit
a
KOH Kind, soang
4) CH,-CH-CH,-CH, wane CHACH=OH-CT,
etanol an
e} Tach loai roi cong hop
oH ve Br CH, CHy
cHy-cH-cH, @\ cu,-bn~ cu," cH,-cH—CH-cH,
Br Br
(OS O* CO
® -. are
ancot
Br
3.8. a) A: buten- 1; B: 2—brombutan; C: 8,4—dimetylhexan.
b) A: 2—metylbuten—2; B: 2-metyl—2,8-dibrombutan
o) Ar OB- CH, CH CH: B: CH, ~ CH CH : buten=2
080,0H ou
4) A: 2-iotbutan; B: buten-2; C: butanol
3.9. a) CH,CHBr—-CHBr-CH,CH=CHBr
b) (CH,),CBr-CHBr—CH,-CH=CH,
¢) CH,=CHCOOCHBr~CH,Br
8.10. 1,4—dimetylxiclopentadien— 1,3.
3.11. Hexen-2
3.12. Cily~ CH, ~ G= CH ~CH,- CH, -CH=CH -CH,—CH,
cH,
3.13. Khi oxi héa manh hidrocacbon d&u tao thanh axit va xeton déu chita 3C,
edn hidrocacbon sau tao thanh axit chifa 2C, cdn xeton cd 4C.
3.14, a) Rita bang H,SO,
hap vao olefin.
b) Caing lam nhw cau a.
©) Tao dibromua, tach khéi n—hexan bang cach cat phan doan va sau do loai
brom bing kem.
gc, vit lép axit 6 dudi cd cha ROSO,OH do cong Hoa hoc Hau co - Phan Bai tap 89
3.15, Penten-2 vA 1,2-dimetylxiclopropan lam mat mau dung dich brom,
xiclopentan khong Him mat mau; penton—2 lam mat mau dung dich KMnO,
3.16. Qua trang thai trung gian c
4.17. b) (CH,),;C-CH,-C=CH,
©
i.e)
CHIC
\
CH,C(CH,),
a) CH
rs =CH-CH=CH,
an
f |cuice |
(ee
3.18. a) (CH,),C=CH-CH, y
b (CH, e) Butadien-1,3
©} Xiclohexen 1) (CH,},C=CH,
3.19. a) 2CH,O + CHO-CHO
tb) Xiclohexanon + CH,O
ch CH,CO(CH,) ,COCH,
3.20. at CH=CH, + 4KMnO, —* — 2K,CO, + 4MnO, +2H,0
Y
b) CH,=CH-C(CH,),-C=CH, + 6KMn0,
cn,
—+ CH,COC(CH,),COOK + 6MnO, + KOH + 2H,0 + 2K,CO,
cH,
+ 4H,S0,-» CH,COICH,),COOH + 4,0
° cy + K,Cr,0
+ K8O, + Cry80,),
a ol + K,Cr,0, + H,S0, — CO, + 18H,0
‘CH,-CH=CH, + MOOG (CH,1,CH(COOHICH,COOH
+ ACrYSOY, + 3K,8O,
8.21. ay CHCH CH CH = CICH,), 90 Anken
e) CH cH. @) CH e CH,OH
on-cu=c2 — > , 3
Hy CiHs FC,
Hy
= OC
3.23. (CH,),CH -CHBr—CHBr-CH,CH,
BH, CO” H,0,
3.24. CH;CH,CH=CH, —2 —~ £3 (cH,CH,CH,CH),COH
THR 10°C OH .
(CH,CH,CH,CH)),C = CHCH,CH,CH,
S—butvinonen—4
‘dun_nang:
cc aN
3.25. a) @ Cach 1 CH = CHM? CH 2 cna SEL cue = cH
CH; Br
CH! Her S8oe
—,CH,C=CNa “2 CH,C=5 C-CH, c=c —
rN
H cH,
LiWCHS), oe CHs
ae cacl
ete, — 70% ao
H cH,
Mg CH,CHO C0,
¢ Cheh 2: CHACL—~ CHyMgCl [2+ CH,-CHOH-CH, ——
a pindin
CH, CH,
CHMacl I Hee x
—+ CH,cocH, — CH,CH,-¢—-OH O=CHCH,
* CH, CH,
Mg CHgCHO. 3 G10,
b) CH,Cl—* CH,MgCl CHjCHOHCH,——. CH,COCH,
ete #0 piridin
Nant CHC! HBr
clsCH CH=CNa. CH,C=CH CH,CH=CHBr
peoxit
Mo cHgcocH, Ca
3 cHCH=CHMgbr —~“cn,cr=cu-é-on
THE HO &
Hy
CH, :
S0Cl,
cx,cH=cu-b-cu,
é1
pitigia ot
Hoa hoc Hau co - Phan Bai tap
Fen,
=CH —+ CH,=CH-CH=CH)
4,0 cu,Cl,
8.26, CaC, +2 CHsCH + CH)=CH-
NH,Cl pe
Y
a Lv. coc, ue L\ conn;
v
3.27. COOH.
Ana L\ xcs oral
4g 07H,0
Pk
—- L\-aony yon =
CH,CHBrCl
4,80, long
NaoBr
3.28, CH,CICH,NO,;
41,80,
3.29. CH,CH,CH,CH,0H [>> CH;CH,CH = CH,
se
H,80, 81,40
> CH,CH,CHOHCH, [4 CH,CH=CHCH;*—“* CH,CHOHCHBrCH,
208
3.30. a) CH;CH=CH, + HC) + CH,CHCICH;
1) BF THE
CICH,CH,CH,
2) CHCGOH ‘
1,80,
b) CH,CH=CH, —C1CH,CH=CHy
Xue tac hidro héa anlyl clorua sé hidro hoa phan hdy lien ket CCl va chi duge
c) CICH,CH=CH, + Cl; + CICH,CHCIC H,C1
ier
propan,
NBS
@) CH,CH=CH, —+ CH,Br-CH=CH, ——+ CH,BrCHCICH,Br
CH,Br-CH—CH,CI
|
1s ,0
e) CH,BrCH=CH
on
8.31. Hap chat a bén. Mée dau néi dai é dau cau nhumg khong phai hé cau
bixiclic. NGi déi trans 1a 6 vong 10C.
Hap chat 6 vi pham quy tac Bret nén khong bén. Vong lon nhat chi cha GC va
ndi doi trans khong bén 6 vi tri dau cau nay
Hyp chat ¢ (nobonen) bén. Néi dai cis khong & C dau chu
Hap chat d bn. Mac dau ni doi 6 dau chu eda hé cau bixiclic, nhung vong ©
8C thich hop véi ndi doi trans
H CyHs HOD. Gis D OH; H
3.32. % Pa 2S ¢ ae
“ oN ai — =
H JW H cl
C.Hs Cl CyHs
6 92
Anken
CH,
cH,tH
3.33, a) .
cH, -)
CH,
ia) (B)
cl,0H
dung dich ki’ Hoe
+ KMn0, — POR,
HO-~ 4
ci,0H
Ad
3.34, Anken phai lA buten-2. San pham cong brom:
cH
Hj 3 Br
CH,CH=CHCH, + Br, —- Hl. -Br
CH,
6a quang hoat
Gia sit anken co cau hinh trans: no vena
Bro CH,
bos
— + Hale -c =H
fog
H, Br
Vay anken la ¢rans —buten-2 “ue
San pham li meso—2,3—dibrombutan
KOH KMn0,
3.35. C\H,, + Bry —* C,11,,Br, — C,H1,,——=" CH,COOH + ¢
Cidien) | D Hoa hoc Hitu co - Phan Bai tap 93
Sw oxi héa dien cd 6C cho ra CH,COOH va CO, vay phai ed 2 mol CH,COOH
va 2 mol CO. Muén eé CH,;COOH phai c6 hop phan CH,—-CH=, con CO, 1a do
=CH-CH=. Vay dien sé co cau tao
CH,-CH=CH~CH=CH-CH, hexadien—2,4) C.
B phai cé 2 brom é C canh nhau, vay vi tri Br la C, va Cy
CH,-CH,CHBrCHBrCH,CH,
ind ita Cyva Cy
CHCH,CH, tts va trans)
Cc phan ing:
eB, KOHietanot
CH,CH,CH=CHCH,CH, —2 CH,CH,CHBrCHBrCH,CH,
“OA . B e
+ CH,CH=CH-CH=CHCH, + CH,CH,C=CCH,CH,
© | amo, €
2CH,COOI + HOOC—COOH
2c0, 4, ANKIN
4.1, a) CHSC— phai la mot trong cdc nhom lién ket v6i C khong tring vat—anh
cing véi hidro, metyl, etyl. Nhu vay hgp chat phai la 3-metylpentin—1
HO=C-CH-CH,CI,
cH,
b) Hop chat phai 1a ankin déi xing co ni ba 6 bén trong
CH,C=CCH, butin-2
c) Néu ankin 6 néi ba @ bén trong thi khi hidro héa bang cde tac nhan
da cho sé thu duge déng phan trans va dong phan cis tung tng. Dé tranh diéu
nay thi néi ba phdi 8 dau mach,
HC=CCH, propin
@HCac CH, Heec oH
weney none
H H H CH,
{2)-penten-3—in-1 {E)—ponten—3-in—1
1000°C
4.2. a) 2CH, —- CH=CH + 3H,
Hg?*, H20
ne
Past, Hee Na
©) CH=CH — CH)=CH, —* CH,-CH,Br “* CH,CH,CH,CH,
b) CHSCH
CH,CHO
NaNH,
cr
qd) CH,—*+ CH,CI CH=CH CH=CNa
Pa
CHCl + NaC=CH— CH,-C=CH — CH,—CH=CH, —
2
Kntno,
CH,-CHOH-CH,0H
ng
+34
0) CHCH=CH) ——- CHj-CH,—CH,Br
peoxit
NaH, CHCH, CHB
HCsCit ——+"CH=CNa —*-2 2
CHCH,CH,-C=Cil +
H,iPd HB Na
CH,CH,CH,CH=CH, —~ CH,(CH,),CH)Br —~ deean
peoxit
NeNH, Ohgt
4.3, a) CH=CH —+* CH=CNa —* CH,CSCH
NaNity CHL
b) CH,-| CH,-C=CNa CH,-C=C-cH,
K
e) CH,C=CCH, oar cis CH,;-CH=CH-CH,
7 Hoa hoc Hau co - Phan Bai tap 95
déng pran nda 2Bty
CH,-CH)-C=cH ? CH,CH,CBr,CHBr,
4) CH,C=CCH,
150°CNeNH,
BH,
©) CH,-C=CH —=2 CH,-CH,-CHO
. HyOz
co + H,0
f) CH=CH CH,=CH-COOH
NiGly
anor
g) CH,C=CH ——= CH,CBr,CH,
1,0
4.4. Cach 1; CH=CH —*~ CH,CHO
Ha80,
H,0
CH=CMgl + CH,CHO =~ CH,CHOH-C=CH
2H Har
CH,-CHOH-C=CH —% CH,CHOH-CH,-CH, ——~ CH,CHBrCH,CH,
Por 5
H,0
# Cach 2. 2CH=CH —+ CH,=CH-C=CH —2 CH,=CH-CO-CH, +
Her
—* CH;CH,COCH, —~ CH,CH,CHOH-CH, —+ CH;CH,CHBrCH,
Na
4.5, a) CH=CH CH=CNa
NH Ieng
NaNtly
b) CH=CNa + CH,CH,CH,1——» C3H,C = CH —-2 C,H;C=CNa
BCH HCl
CH,CH,CH,C=CCH,CH,CH,CL
#20 Fett, Her
4.6. CaC, ++ CH=CH —2 CH)=CH,—+ CH,CH)Br
pi
CHB
Na
CH=CH —~ HC.
NH, léng)
Ne
CH,CH,C=CH
Br
KOH HBr
4.7, CHjCH,CH,CH,Br ——= CH,CH,CH=CH,——» CH,CH,CH-CH,
‘anco! 3 >
oO Br Br
?°KOH Br, KOH
= CH,CH=CHCH, —* cH,H-GHCH, (> CH;C=CCH,
ancoi ancol
Mg
4.8. CH] — CH,Mgl
CHyMot
4,0
aC, 2+ CH=CH 5. AREN
5.1.» Dong phan mat géc ankyl:
n= propylbenzen; isopropylbenzen
* Dong phan hai gée ankyl:
o—metyletylbenzen (1—mety)-2~etylbenzen);
m—metyletylbenzen (1—metyl-3~etylbenzen);
p-metyletylbenzen (1—mety!—4~ctylbenzen)
+ Dong phan ba géc ankyl
1,2,3-trimetyibenzen; 1,2,4—trimetylbenzen;
1,3,5-trimetylbenzen.
5.2 a) NO,
NO,
NO,
i
“ °
CH,
246.trinttototen
(£)-3.4-(4.4" ainigroxidiphenytnexen 3
rN
» a )-on -c1 OOH
| a ES
CCl, .)
¥
NH,
4.4°~ diclodipnenyitectostan, axit p -aminodenzoie
5.3. a) Vong benzen logi gidp thing e¢ tién 26 benzo [")
i) Tetralin hoae 1,2,3,4—tetrahidronaphtalen;
ii) Inden hoac benzoxiclopentadien;
ii) Benzoxiclobuten (xiclobuten vi C=C chung cho hai vong duge coi nhu
trong vong 4)
iv) Fluoren hoge dibenzoxiclopentadien.
b) Tir ortho khong duge dua vao vi vide giap vong chi thye hign voi hai
vi tri nay. Vi tri tiép gidp nao khde thi phai dia vao.
5.4. a) Etylbenzen; o—xilen;
by p-xilen;
c} Btylbenzen; o~xilen; p—xilen
Tal Ngoal fi trang hop c6 tén théng tudng nb trong tit Hoa hoc Hau co - Phan Bal tap 97
5.5, CHCl 15,80. ph a. Hs
™ —_ a a SO3H
a) © ao } om Cy 823!
G
cH, CH, cH,
»» a (CH,),Co a HNO, Non | NO,
O). acy u 2 B
ocH; ‘OCH, OCH,
C(CH,)4 GiCH,)
5.6. Cong thie phan ti eda hop chat ditge hidro hoa hoan toan C,H, ching to
s\ eS mat hai vong. Vige hink thanh axit phtalic cho thy mgt trong hai vong phai
la benzen va 3 cacbon cin lai phai la mét phan cua vong 5 canh cé mot canh chung
vai vong benzen.
YS @O % Co
bixicla L439] nonan
inden indan
5.7.
4
” 7 Ke H
He
| COR Ol
BH, | ON”
B
QOH oH
(CY noe. Ore saben) OS
Ag hiéro phan
fran A ravermic
H
b a H
Hey %
OD“ Cate. | oft |
AD | r
t |
— Pa +?
(2) Cl, Fe;
(4) OHT, p,
(2) Cl,, Av;(3) Na, ete
§.8. a) (1) CyHACl, AICI:
(3) KMn0, + H,SO,;
b) ) CHAO) AIC: 98 Aren
5.9. a) m—clobenzoclorua
b) Axit picric
¢) 2,4—diclonitrobenzen
4) p—clopheny!—p-tolyimetan
e) Axit 2—metyl—5—isopropylbenzensunfonic
Alc
5.10. a) C,H, + CH,CH,CH,COc] 2 ¢,H,cocH,cH,cH, 4
— C,H;CH,CH,CH,CH,
No, NH,
» Om oO 0, 6
Os ASO, NNO NE
5
NaNO, + HC! cuc
0-5°C
NH, NHCOCH,
, HNO, {CH,C0),0
e a EON ——
1,50,
NHCOCH, NH,
H,S0, — NO. WHsO*
ae 10 Oo 2 2 Co
‘ $0.8
cl a a
ly HNO, 1,80, oS No.
d —_— — ‘NO. 2
Os CS ro) IO
$0,H
cn, CH; CH, CH,
HNO, 7 (CH,C0},0
sana 4 can 2 (O) ae () & ‘O) AoO' om
a No, NH, NHCOCH,
cH, Hs
Br HPO
a Ce. Lae Te ©.
NHCOCH, Héa hoc Hau co - Phan Bai tap 99
@ Céch 2: Hoac cé thé tién hanh clo hoa nhom -CH, bang Cl, khi dun néng
hoac chiéu sang sé nhan duge ~CCI1,, nhém nay dinh hvéng meta. Sau khi brom
hda, nhém —CH, duge phuc hdi bang phan tng khit voi Zn trong axit
CH, CCl, cel,
COs G, 2 @
hose 2 hode Av or Br
eF
b) C,HyCH, + (CH,),CCl 2 p-(CH,),C-C,H,-CH,
Nhoém ¢tert—butyl bén ydi sy oxi hda, do do nhom CH, bi oxi hoa triée thanh
axit p-tert- butylbenzoic.
Bi
er Ma cH,cHO
5.12. a) Oo a —. cyHyMgBr
FeCly ete khan ete khan
H,0 [0]
—— > GHjCHOMgBr —E- C,Hs;CHOHCH, —~ C,H,COCH,
3,
80,H O31
» © H,80, ar, KOH, KON
Pech, Gua che
Br ”
LCN CONT, COOH
H,0 H,0
—_- ne ai
e Br Br
5.13. a) Hidrocachon thom CyHy khi oxi hda cho axit benzoic vay chi es mot
mach nhanh chia 3 nguyén td C (vi cha hai mach nhdnh thi khi oxi héa cho
diaxit). Cong hgp voi 2 mol Bry vay cd thé 1a mot néi ba hoac hai ni déi. Nhung
tac dung véi AgNO, trong NH, nén phai la mét ankin 4 dau mach. Vay C,H, la
benzylaxetilen.
gecu en (©)
ba, 1,1,2,2—tetrabrom—3~— phenylpropan.
CH,-CBr,CHBr,
AgtNity) gH
OS | aaihradal C,H.CH,CeCAg| + 2NH, + H,0
axetilua bac
2
70. (One + 200, + H,0
OH
axit benzoic 100 Aren
b) Lap luan nhu trén dng phan C,,Hjy cd cOng thie C,H.CH,CH
(4~phenyl butin~1)
C,H,CH,CH,C#CH + 2Br, + C,11,CH,CH,CBr,CHBr,
C,H.CH,CM,C=CH + [AgiNH)),JOH + C,H,CH,CH,C=CAg\ + 2NH, + H,0
C,HsCH,CH,C=CH + 100 + C,H,COOH + 3CO, + 2H,0
c) Hai dong phan la
HCH;
va
oH.
2H
at cu,cx,O-cnen,
uc
Eee enycn,—(Q)-e=cou + NH,Ci
NH
ep
ee CHC; (C)-cH.0
cy =c-(C})-cit=cn, —
bar
an cHtsircnBr—(O) CHBrCH,Br
cHtjcH,—{C})—cacn + 2Bry — CH,cH, —(O) Cir CBs,
5.14. a) 8—etoxitoluen
b) m—tolylaxetat
©) 2,4,6—trihrom—3~metylphenol
4) 2,4,6~ tribrom—3- (tribrommetyl)phenol
©) 2—metyl=1,4—benzoquinon
f) 2,4-ditert—butyl-3—metylphenol. 6. DAN XUAT HALOGEN
6.1, a) 4—metyl—2—clohexan;
b) 2—phenyl—4—iot—6-
¢) 8-brom—4—etyl—5
ylnonan;
jot xiclohexen—1;
d) 2—-brom—4-iot -clobenzen.
CH,
6.2. 0) CHy-CH—-C-CH,CH,CH,CH, b) —
Br Br OH,C1
H
1
° Li a e)
Be cl
cl H
H
cl
6.2. a) Co ba déng phan lap thé khong déi quang:
4 Ch.
H He Sts 4
2 a
Hg H Hal cHy
. H
en 4 H
cH H
3
cL ct Hod
a) (By ©
B khong phan tng vi cdc H bén canh d vj tri cis va khong dng phang véi Cl
A va € phan dng duge va cho 1,3—dimetylxiclohexen
b) cH,
6.4. a) Co hai anken:
(CH,);C=CHCH,CH, —_ |
CH,-C-CH,CH,CH, (A)
CH}=C CH,CH,CH, — I
CH,
CH,
cu,
HBr I
b) CH, = CHCH(GHy), [oe BrCH,-CH,CHCH, (B) 102
c) Co hai anken:
Dan xudt halogen
CH, oH, CH,
2 01 Cy Hel Cy
«ey
+Ag0H
6.5, a) CH,-CH-CH,Cl ——» CH,-CH-CH,0n
1 “ —AgCl 3 2
CH, Hy
+4,01880
b) CH3-CH-CHCl CH3-CH-CH,OH
CH, Hs
KOHretane!
©) CH,-CH-CH,Cl CH,-C=CH,
CH, Hy
+KeN 4,0
ad CHy-GH—-CH,Cl CH,—CH-CH,CN = CHy— GH -CH,COOH
CH, CHy CH;
e) CHy-CH-CH,Cl Neel CHy~ CH~CH,NH;
CH; * CH,
9 CHs-CH-CH,CI
cH,
Mg
g) CH;-CH-CH,CI
ay ete khan
CH
cH,COONa
h) CH,—CH—CH,¢1
CH;
KsH
9) CH,-CH-CH,Cl CH3-
CH,
Na/C HOH
6.6. a) CH,CH,CH,CH,I
1,06)
CH;CH;CH,CH,] —2——"_.
KOHetanol
CH,CH,CH,CH,I
KOHretanot
b) CH,~CH)-CHBr,
KOHjetanol
c) CH;CI-CH,—CH,C1
CHy~GH-CH,~CH,—CH-CH,
CH, CH,
+
Fetin CHs-CH-CH,MeCl
CHy
H;-CH~ CH- OCOCH,
Hy
CH-CH,-SH
CH;
CH,CH,CH,CH, + HI
CHCH)CH,CH,0H
CH,-CH,-CH=CH,
sen
CH,-C=CH.
CH,CBr,CH,
anor
CH,=C=CH,—* CH,CCI,CH, Hoa hoc Hau co - Phan Bai tap 10a
6.7. a) > C)H,OCH, + KI Sy2
b) + (CH,),C=CH, + Nal EL
c) + CH,=CH-CH,OCOCH, + NaBr Sy!
4) » CH,=CH, + MgBr, B2
e) > CH,SCN + KI Sy2
1) + 2CH,-CH=C(CH,), + 2Agl El
g) > C1-({)—CH,OH Suz
68d >b>ar0
6.9. a) CH,=CH-CH,Br + (CH,),CHMgBr
b) CH,=CH~CH,Br + Br,
c) CH,=CH-CH,Br + HBr
dj CH,Br-CHBr—CH,Br + KOH/ancol
6.10. C,H,NH,-+ C,H,NHCOCH -~ p—BrC,H,NHCOCH,—
p-BrC,H,NH,— p-BrC,H,N,CI~ p-BrC,HyI
6.11. C,H,CH,CI— C,H,CH,OH
CHCHCl,—~ [C,HsCH(OH),|—> C,H,CHO
C,HCCl-= [C,H,C(OH)CI,]— C,H,COCI—> C,H,COOH
6.12. C,H,OCH,—> p-BrC,H,OCH, > 2-nitro—4—bromanizol —
——= — 2-amino-4—bromanizol.
6.13, a) X = isoamyl iodua; ¥ = isopenten—1;
% = 1,2-diclo-3-metylbutan
b) X= 2,4—dimetyl-2-iotpentan; ¥ = 2,4-dimetylpenten-2
Z = 2,4-dimetyl—2,3—dibrompentan.
6.14. a) CH,CH,COH(CH,)CH,CH, + CH,CH=C(CH,)C,H, + (C,H,),C=CH,
b) Chuyén vi CH, san phdm chinh (CH,},C=C(CH,)) va
(CH)),CHC(CH,) OH
6.15. 408 fia
HOBr
CH,-C(CH,)-CH)-CH CH,-C=CH-CH, —* CH,-C-CH-CH.
8 EC Ca CH same OT 3 a $
Br CH, 80% OH Br 104 Dan xuat halogen
CH, CH, CH,
» cH =c Sc cr,-cn, “SS e-cn-cu
a N téi “wt 2 * er a “
CoH, CH, Br CH, 80%
OH” A
© (CH3);CCl —+ CH, =C(CHy), —~ (CH) C1
Har
4) (CH),CC1 CH,=C(CH;), ——~ (CH,),CHCH,Br >
peoxit
“I
(CH,),CHCH;I
Sxeton
6.16. CHCl + I> a= CHI + cr wD
OHI + OH” — 6,H,OH +17 (@
C,HyCl + OH" ++ C,H,OH + CI- «)
Tac dung xtic tac eda I~ trong phan wing (3) do la ket qua eda phan wing (1) va
(2), eae phan ting nay xy ra nhanh hon phin dng (3) néu phan ding (3) khong co
I xe tae.
6.17, Dimetylaxetilen
6.18, $0,H $0,H
=e) ; Bla Oo. sew [Oh 7 Dla G.
Br Br Br Br HO OH
Ag* + HOH
6.19. CH,CH,CHBrCH,—+ [CH,-CH,—CH-CH,) =! cH,cH,CHOHCH,
4,0 Sut
Nal er
CH,CH,CHICH, + NaBr CH,-CH=CH-CH, + H’
6.20. a) Xay ra phan Ung tach cho CH)=CH,
b) Phan tng clo hoa khéng chon lec ma cho mot hén hop clopentan
@ giai doan 2 xfy ra tach va eho penten—2
c} Peoxit khéng ed higu ung voi HCl. Giai doan 2 tach eho isobuten
d) Giai doan 1 sai. O 2 khong co kha nang tao tac nhan Grinha.
6.21. (1) Sai vi hop chat nitro khong tiép nhan phdn Gng Friden—Crap
(8) Sai vi phai halogen hda cacbon baie hai
(5) Sai vi diéu kien tach nuéc la can H,SO,, nong.
6.22, a) (CH,),C=CHCH,CH,Br
b) CHCI=CCl,
¢) BrCH,CBr=CH,
4) C,H,CH=CHBr + CO, H6a hoc Hau co - Phin Bai tap 105
6.23. 0, ¢, g.
10
6.24. CH;CH,OH——- CH=CH,
CH)-CH,
H,S0, ‘Ags? Ny
CHa “OM
Her Mg
CH,CH,OH —- CH,CH,Br — CHCH,MeBr —=
9
Har
—- CH,CH,CH,CHy 201 CH,CH,CH=CH, — CH,CH,CHBrCH,
120
° Cl 400°C
6.25. CH;-CH,; —~ CH,=CH,—*= CH,CICH,CI—= GH, =CHCI
H,OHg?* OH™ loang e
6.26. ¢ Céch 1: CH=CH = CH,CHO CH,CHOHCH,CHO—
12804
ad AI,03
—~ cu,cH=cu-cno™2 cn,cny CH,CH,OH
pe
Ma
8
—+ CH,CH,CH=cH, —2 CH.CH,CHBrCHaBe
eH, Or
+ Cach 2: CH=CH ae CH,=CH, “= cH,cH,cl “. cH,CHyMgC
pr
0, oHgMgCt Al,03
CH=CH, 5 CH,-CH, = CH,CH,CH,CH,OH +
rate Ng Fro
——- CH,CH,CH=CcH, CH,CH,CHBrCH,Br
Hel
% Céch 3: CH2CH {= CH,=CHCI CH,CH,Ci
200°C, pe
CHyCH,CI FoH,
cHscu ™ CH= CNa cH,CH,C=cH ——4
NH, lang Mp
— CH,CH,cH=cH, — CH,CH,CHBrCH2Br
4,80, Nadi
10
6.27. CaC;—*+ CH=CH
CH;CHO CHI,
HgS0,.H,0
6.28. a) Dang thuy’n cd nang luong cao, kém ben nén chung ta khong quan
tam. Dang ghé ben hon va Br co thé 0 vi trie va a. Chi khi Br 6 vi tri a méi co
thé tach cde Ha 4 2 C bén canh
HH
AH
Hoon 4 er
Br, (khong 6 rans— diaxial) Bry (rans = diaxialh 106 Dan xuat halogen
Vi Br, od phan tng tach nén Br, chuyén dan sang Br, cho dén khi phan dng
két thie (ed cain bang cia hai dang e va @)
b) Cis—2—brom mety!xiclohexan
Br 2 z . 2
CH3, “Hy
H H
vrans-2-brommetyixicionexan —_{-melylsiclohexen (4) Semetyixiclohexen (8)
Br
H
: H
— chicho san phém (B) CO
CHg
H CHy
H,
6.29. 2) Bo %,
aos
CH ‘Br
Il
H
H
CHy
Br
81 quang (RR) H6a hoc Hau co - Phan Bai tap 107
6.30. Day la phin ing thé Sy2 voi su quay cau binb:
a) (8) - CH,CH(OCH,)CH,CH,
b) (R) - CH,CH(OCH,)CH,CH,
©) rax, trans—4—etylxiclohexanol
6.31. a) Br Br, H
H , é H 2 Cis 208", x of
ae CH, = —- o% “cx,
I Ho‘) CH, |
Br Br cH,
ans) catalan
Br¢Br Br
b) catts by to acbecu C,H,C=CH——
Hs 5 Ws CRE Hy
HNO ano
Mia oyucec~ 22 C,H,C=CH
ons os
Vi H axetilenic ed tinh axit va trong diu kien dy NaNH, sé tao mudi natri,
nén dé tach sin phdm cudi cing cAn phai axit hoa
c)
chy Boo
Br 4
CHs
CHy
CH3
CHsOH + Bro +
H
H Br frans-puten-2
CH; CH
6.32. a) (ia) CHs-6 CH-CH,; (1b) CH,-0-CH-CH,
CH, HO OH
CH,
1
b) (2a) (CH;),C=CHy; (26) CHa-C-CHls 2ey{CH,),CCH,OH
/
0 OH 108 Dan xuét halogen
©) (Ga) CH,CH = CH-C,H, ; (35) CH,CH,CHCICHy
(3c) CH,CH,CH(OFDC,H, ; (3d) CHyCH,-C-OCH(C;HS);
t
d) (4a) CH,CH = CH, ; 6) CHyCH,CH,Br ; (4c) a—hexan
e) (6a) buten—1 ; (5) butancl-1
(6a) CHjCH = CH, ; (66) BrCH;CH =CH,; (6c) HOCH,CH = CH,
6.33. Chat vita od tinh di nhan tot vila od tinh bazd yéu sé 06 khuynh huong cho
phan ung $,2, dé la I” ; CH,NH, ; CH,S~
Chat vita co tinh ai nhan yéu vita ed tinh bazd manh 6 khuynh hudng cho phan
ing tach E2, do la
NH; ; C,H,” / C;H,OH, 7. HOP CHAT CO MAGIE
7.1. a) BrMgC=CMgBr + CHSCH—~ CH=CMgBr
CHACN
b) | BrMgC@CMgBr "> CH,-C-C#CH
Hi x
Mgo=CMgBr 8" cu, c-c=c-¢~cH
Bi es i: —. —C-C=C-c~
Mg gBr ot f % Is
2CH, = CHCH,CI
co) BrMgC=CMgBr
CH,=CHCH,C=CCH,CH=CH,
HCHO.
4) BrMgC=CMgBr —- HC=CCH,OH
120
2HCHO
BrMgC=CMgBr ——— HOCH,C=CCH,OH
2
cl
7.2. a) CH,CH=CH, —- CH)=CHCH,CI
500°C.
Her Mtg
CH,CH=CH, —» CH,CH,CH,Br —= CH,CH,CH,MgBr —~
peoxit
CH, =CHOH, Ct Br,
CH,(CH)),CH=CH, —* CH,(CH,),CHBrCH,Br —
-2hBr CH,CH,CH,MgBr
——+ CH, CH,),C=CH CH,(CH,),C=CMgBr =
188 CHACH,CH,CH,C=CCOOH
2) H,0 eee
axit heptin-2-oie—?
N 2Her
b) CH)=CHCH,CI—- CH, =CHCH,-CH,CH=CH, —-
“
3, CHCH(CH:). CH- CH
.
ee
MgBr — MgBr
CH,—CHBr(CH,),CHBrCH,
co,
CH,-CH-CH,-CH,-CH-CH,
anon Sy I
coon cooH
HBr Mg
©) CH,CH=CH, ——» CH,CH,CH,Br —~ CH,CH,CH,MgBr
peoxit
HOH [Ol
CH,CH=CH, —» CH,CHOHCH, —~ CH,-C-CH,—
3 2 5! 3 aT ORs
0 110 Hop chat co magie
CH;
1) rt, CH,CH,Mgor i
a CH,CH,CH)-C-OH
2) HOH i
CH;
CH,CH,CH,Mger
KN
@) CH;CH,CH,Br —+ CH,CH,CH,CN
> CH,CH,CH,-¢-CH,CH.CH,
,0 Her
7.3, a) CHSCH —~ CH,CHO —~ CH,CH,OH —~ CH,CH,Br —~
Hgs0,
Mg fot ¥ 260,
—— CH,CH;MgBr BrMgC#! “CMEBr HOOCC=SCCOOH
)
1) BrMgC=CMger
b) CHSCH ~» CH,CHO—- CH,COOH — CH,COCH,
2,0
OH on
> CHy-0-CaC—6-CH,
CH; CH,
HO Mg
©) CH=CH —-s CH,CHO—+ CH,CH,0H —~ CH,CH,Br =
#980, ote
CH,
1) CH,COCH, I
—— CH,CH.Mgbr CH,CH,-C-OH
. CH,
er, ~2Har
7.4, a) CH,\CH,CH=CH, —+ CH,CH,CHBrCH,Br —~ CH,CH,C=CH +
OH
HOH 1) GyHgMaée i
C1RCH,COCH; CH,CH,CCH,CH,CH,CH,
1
; CH;
CyHgMaer 1) CHyCH,COCH,
*) CH,CH,C=¢H CH,CH,C=CMgBy
2) 4,0
OH
|
——- CH,CH,C=C-C-CH,CH
3CHy i 2CHy
MgBr (xem 7.3.a)
1) CHyCHO
C,HsCH, C,HyCHAC]—= CCH MeCl
a
19] BrMgo =CMger
——- ¢,H,CH,CHOHCH, — C,H;CH,COCH,
4,07 Héa hoc Hau co - Phan Bai tap mW
GH Gs
— CoH; CH,~C-CaC-C-CH.C, Hs
OH OH
7.5. I. Dietylxeton; II. 3-etylpenten-2
7.8. Hda tan hdn hop trong ete va thém mot Iugng magie vita di. Khi do
jotbenzen chuyén thanh phenyl magie iodua. Thém nwée vao hén hop phan ting,
phenyl magie iodua co thé chuyén thanh benzen trong khi dé metyl ete cia
p-crezol khong bi thay déi. Hén hgp hic nay gdm co benzen (¢, = 80°C) va mety!
ete cla p—erezol (¢, = 175°C) cd thé phan tach dé dang nhd chung c&t
ety ono
7.7.0) ¢ ROH —* RX —+ RMgX Tao RCH20H
He
Cle Ch
1) HX ‘ oe
@ ROH —~ RMgxX RCH;CH,OH
2) Mg 4,0"
~cHy
# ROH —» RMgX RCH,CH,CH,0H
4b) Didu ché RCH(CH,)OH
yx HoH sO, CHMox
« ROH —+ RMgX ——~+ RCH,OH RCHO--—» RCH(OH)CH,
2) Mg K,Cr,0, H,0
HX KCN CHsMax knd
» ROH — RX — KN R-COCH,—+ RCH(OHWCH,
2
@ Diu ché RC(CH4),0H
nx HcHo ox
»* ROH ——~ RMgX —+ RCH,OH— RCHO— RCH(OH)CH;—
2) Mg H,0 ao
CH,
01 cugmox
—- RCOCH, R-C-OH
CH.
01 HX RMeX 3
ROH ——
. 2 ve ® CH,
te R-C-OH
KCN CHsMaX CH,
a
CHjL ~—- CHjCN ——- CH,COCH, +
H,0 112
Hop chat co magie
@ Didu ché RCH(CH3)CHOH
HK HCHO
« ROH -- RCH(OH)CH; — ROHCH, ~~ RCHCH,
v9 2
MgX _CHOH
Hx KCN ‘CHMgX hd
+ ROH — RX —~ RCN » RCOCH; — RCH(OHCH, +
B
tiép tuc nhu trén,
WHX HCHO {0|
©) @ Cach 1: CH, Fg C2MaX “> CyHsCH OH —> CZH,CHO =
2 CH,
CH; Max } HX if
= crycH,cHOneH, ~ Fg 2HSCHCH, <-> C,H CHCH,CH,O#
MeX . CH;
(0) CHyMaX 10)
+ ©:Hs~CH-CH,CHO— > —~¢, sHyCHCH,COCH, —+
cH, cn,
CH, —Ch,
CH. 2 Che cH
CligMoX é- 3S yHx 0% 3
C;H;CHCH,-¢-OH ~~ CH CHIC, -G-cH,CH,04
H,0 2)Mg HOH
cH, on, ou, cH,
Fomandehit, etilen oxit va CH;MgX dita ché tir etanol:
C)H,OH
@ Céch 2: C,H,OH
H,80, 2 kod 1) Hx
CH,=CH, —= HCHO + CH,OH —~ CH,Mgx
eee FH en Fag NE
180°C.
4
CH,CHO
+
CH,COOH
4‘
CH,-CO-CH,
Har CHyCHO.
Ma
én, cH,
Her
C,H;OH —» C,HsMgBr Ton CH,CH,- CH-OH-— 2Hs—CH MgBr
Mg Hoa hoe Hite co - Phén Bai tap 113
Hoe cH,cocH,
HCHO CH,CH,CHCH,OH —— — CH,CH,CHCH,MgBr__*
i 9 | 1,0
CH.
CH, 3
cH, Rect cH,
| He °
— C,11,CHCH,-Cou C,H,CH-CH,CCH,CH,OH
| | . | |
CH, CH, CH, CH, 8. ANCOL VA PHENOL
on
600°C 280, H,0
8.2, a) CH,CH,CH; —» CH,CH=CH, = CH,CHOH, cH ,CHCH,
0s0,H
600°C 1,80, Na,Or,0,
b) CHj-CH,; —= CHj=CH, 2 CH,CH,O# CH,COOR
Hor 7280,
ThO, NaBH
— ++ CH,COCH, CH,~-CHOH-CcH,;
450°C.
600°C 1) BAHg
©) CHyCH,CH, ——+ CHCH=CH, = CH,CH;CH,OH
202
a
600°C cso
4) CH,CH,CH, —= CH,CH=CH, — cHy~CH- cH,
bu
OH™ H,O*
—- CH,-CH-cH,—~ cH,- CH-CH,OH
N
o on
a) (CH,),CHMgBr + HCHO
b) CH,CH,MgBr + CH,COCH,
©) CH,CH,MgBr + CH,COCH, r6i tach nude
@) (CH,),CHMgBr + CH,-CH, + (CH,),CHCH,CH,OH —
No’
(CH),CHCH,CH,MgBr + HCHO; tach nude
©) (CHy),CHMgBr + CH,COOC,Hg tich nude, hidro hia,
) CH,COCH, + CH,MgI + (CH,),COH + (CH,),CBr +
HCHO
—— (CH,),CMgBr
(CH,),CCH,OH
8.4. a) C = 3,3-dimetylpentanol -
b) A = toluen, D = triphenyletilen
8.5. (CH,),CHCHOHCH,
8.6. OH OH H By
a
CH,COGI Br tr HOH
acer €
NH) NHCOCH, NHCOCH,
“OH (0) CHsMeBr
8.7. (+0. Ci = CHO(CH),CHO —=——
OH HOR H6a hoc Hau co - Phan Bai tap
115
——+ CH,CHOH(CH,),CHOHCH,—
~H,0
+ CH,CH=CHCH,CH,CH=CHCH,
8.8. Khi dehidrat héa thanh dien, oxi hoa tiép theo bang axit cromic, diol dau
tién cho dixeton C,; cdn diol thit hai cho diaxit C,.
8.9.
8.10.
8.11
(A) C,H,OCH,-CH=CH,;
B) -OH
-CH,CH=CH,
(€) OH
-CH,-CH.
i)
~
CH.
Noo”
OH
F5)- oH CHO
(Dy
(E) HCHO
(FY
a) (CyH,),0;
b) (CH,CH,) ,CHOMgBr + CH,
©) 2CH,CH,CH I
Hy
HOH + CH)=C¢
d) CHCH,
CH;
€) (CH3);COCH,CH,CH,
f) CH,CH,CHO
8 ¢
(6) OCH,
6 —CH,CH=N-OH
a) OCH,
Ep euen
@ ocH,
(Gy econ
W) — QCH,
(x) a
-C\Hy
©
w (6 7eHs
h) CH,CH,CH,SCH,CH,CH,
i) CH,CH,CH,Br
k) (CH,CH,),CCH,CH,CH,
br
1) (CH,CH),CHSCH,
Br
m) CHBr + CH,CH,CHCH,CH, 116 Ancol va phenol
b) CH, CH; CH;
O ot, NaoH
a ae
cl OH
hoae nitro héa toluen vA chuyén thanh phenol théng qua mudi diazoni
oO oH
_CHyth tO) lt
" 2nCy/HCl OH
vi On Cos
Ht —
cl
a oe CH; Hy
Q a CO) oa O
i
Pe cH 0
on
©) CH;CH,CHO + CH,CH,CHO—> CH,~CH,~CHOH-CH-CHO-
CH.
hd ‘
ao? CHsCH,CHOHCHCH,OH
CH,
8.12. a) Gis b) CH;-CH-CH-CH-CH3
CHy-C-CH-CH, CH, OH CH,
OH OF
CH, Br oH
@) CH,- c- cH o- cH- CH,-CH;
on oH, a cH CH;
CH;
8.18. C)110H..0-C3M, CcHsOH...0- Cull
H H
a ap
C,MsOH..0-CiH1, CH JOH..0-CyHi,
H H
ap av)
Dang III ben viing nhat vi nguyen ti hidro trong ahom OH eda phenol co tinh
axit ln hon cia ancol va nguyén tit oxi trong nhém OH ca ancol lai es tinh bazo
lan hon eta phenol. Hoa hoc Hau co - Phan Bai tap Wz
8.14. a) KhOng ed vinylancol vi vay khong thé cé J. Gi stt ed vinyl clorua thi
2 gay tring bap
b) 1 duge, 2 sai vi halogenwa bj khit thanh hidrocacben no.
ec) 1 sai vi Cl, oxi hda, Cl, cdng khong wu tien tain cong € s6 3; 2 sai vi
hop chat Grinha sé phan ung voi chinh no
8.15, a) C,H,OH + SOCI, + C,H,Cl + $0, + HCI
b) CH,=CHCH,OH + HCi dam dac + CH,=CH-CH,Cl + H,0
¢) CH,=CHCH,OH + 2HCI khi — CH,CHCICH,C) + H,0
4
a) LIAIH, + 4(CH,),CO =[(CH,),CHO],AILi ~ (CH,),CHOIT
3 [ -on + K,Cr,0, + 4H,S0,—~ 3 [> 0 + 7H,0
+ K,80, + Cr(S0),
Cl, KOH
8.16. 9) CH;CHy —+ CH,GH,Cl —~ CH, ot
crane!
CHUH MgCl CH, GH,
No
0
Hy SH,
=H,0
CH,CH)MgCl —s, CH,CH,CH,CH,OH— CHj-CH,~CH= CH,
r 7
o. fa Nao,
* = CH,CH,CHO.
CH,CH,CH,OH
4,0
{CHy),80
bw
») CH,CHy [> CH,CH,C1 CH,CHO
2 Wim
KOH 0, Zn NaBH, S001,
CH,CH,Cl — CH,=cH,— —, cH,o —" cH,on ——=
eianol H
CH,CHO HAO -#,0
Mg
—~ CHCl — CH Mgci
ee
——= CH,CHOHCH,;
Bhs M02
——~ CH,CH=CH, — 22° cH,cH,CH,OH
THF OW
©) CHjMgCl + CH,-CH,
0
Br, Mg C0, 450°
4) CRACH — CHjCH,Br —~ —2 CH,CH,COOMs'r —
LIAIH,
—~ CH,CH,COoH CH,CH;CH,OH 118 Ancol va phenol
Br, KOH RCO,H
8.17. CH,CH, —*+ CH,CH,Br CH,=CH, —
fw C,H,OH 28°C
H0* KMnO,
CH“ CH, = CH, CH,
No” 25°
ou OH
UAH,
8.18. a) CH,CO-CH-CH-CH; CH,-CHOH-CH-CH-CH,
tr 1 AM(0-1=CaHy by i 1 3
CH, CH, CH, CH;
4,0
>) CHyMgX + HO-CH-CH-CH,
O CH, CH,
(CH CH
©) CH,CHO + /CHMgX
cHy
2 dang dong phan cH,
H |-On
CHy}-H
GH,
coytheo tren
Cu, 325°C
8.19. a) CHjCH,OH --——+ CH,CHO
300°C, 300a1m u.g25°C
cO + H, CH,OH ————~ HCHO
2n0- 61,05
CH,OH CH,OH
NaoH HCHO
CH,CHO + HCHO HOCH,- c cHo ——— HOCH,- c CH,OH
On”
chy OH cH, OH
Her Mg
b) CH,CH,OH ——~ CH,CH,Br — CH,CH,Mair
Na,Cr,0, CH,CH,OH
CH,CH,OH CH,COOH CH,COOC,Hy—
3 380,
OH
HCH, MgB 1
nowt CHaCH2~C-CH,CH,
. CH;
Tho, NaBH,
¢) CH,CH,OH—— CH,COOH “Gigeg CHsCOCH, —~* CH,CHOHCH, ~ Héa hoc Hau co - Phan Bai tap 119
SOC, Mg
2 CHy-GH-C1 —* (CH,),CH gCl
CH
H,80, A 1) {CH,), CHMgCI
‘o
CH3CH,OH 3" CH)=CH, ==, CH, CH, -
180°C. OP ONG 7 a Ho
—+ GH,-GH-CH,-CH,OH
CH,
600" Cly+H,0
8.20, CH,CH;CH; ——~ CH,CH=CH, “> CH,—¢H—-CH, —
OH Cl
on” 1,0"
CH,-CH-CH, CH,-CH-CH,
id
No® OH OH
80,H ONa OH
8.21. 1,80, Naot ro
©, Oy.
‘$O3H ONa OH
8.22. b) fox CL) CH, ehinh
OH
H
°
8.23.0) OCH; ou
A Her Ag20
Ay Os oH [=o
( P ate, NazSO, oe
» on OcH,CH=CHCH, On CH=CH,
1 | | _CHCH,
O NaCH — CH,CH=CHCH,CI
i |
CH; CH,
OH CH,CH,
HAI
—. (O)-cuen,
CH;
8.24. cH, CH, CH,
LF H,80, a
Son os Br
: ROOR|
t-melyixiclohexan 120 Ancol va phenol
8.25. .~ OH
cy NajCrg0, == 0 1} CHaMgBr con 4,80,
SA iy cad CH
CH, CH;
I HBr aa
nook = \_ Br
8.26. Méi mot tosylat gitt nguy@n edu hinh cia ancol ma ti do né duge
thanh, Sy tich véi etylat la tach £2, dai héi dong phang vA OTs va H phai o vj
tri trans
H.
Sts ucts CHy
h ey Lo
H H H
oH OT»
trans ~ancol ans —tosylat a-metyixiclohexen
af H CHS
chs cHy
H
H —~ H —
oH
OTs
sis -ancel cis—toaylat ‘metyixiclohexen
anhax
8.27. a) C,H, ou
C,H ,COCHy.
Ail 1
iz €,H;-C-CH,CH CH,
I
Mg
2CyHyBr + nCyHyMeBr CH,
ote
Kou Bre 2NaNHy
b) CH,CH,Cl ——- CH,=CH, —*+ CH,BrCH,Br
ancol
CH=CH
CH,
cu,-0-c=cH
on
kon Nas
c) CH,CH,CH;,Cl —- CH,CH=CH) — BrCH,CH=CIL, —~
‘ancol
CH, Moa cH,COCH,,
CH=CMgBr
cH.
Mg GHgCOCH, t s HpSO,
——= BrMgCH,CH=CH, CH,-C-CH,CH=CH,
ee ;
HH Héa hoc Hau co - Phin Bai tap
121
CHs-C-CH- CH=CH
CH;
CH, CH,
CHyMal 1 #80, T
@) C,HsCOCH, —"* C,H,- C-CH, + C,H; C=CH, >
oi
1) BH (THE
—-—_» C,lix— CH-CH,OH
2) H,02, OH I
CH;
8.28. 2) Phan ting thé Sy2 khong thuc hién vdi ankyl halogenua bac ba
b) Jonancolat 14 mét bazd manh, dé la tac nhan nucleophin va phan dng
tach chiém uu thé:
HOCH,
cH
IX I £2 4 *
CHCH,CHO“NaY + H-C3C-CH, —+ CH=C° + NaBr +
I
Gr CH;
CH,CH,CH,OH
c) Phuong phép téng hop t6t han do 1a ding phan tit phan cing Sy2 c6
nhém ankyl it can tr hon va ancolat cé nhém ankyl cén tré nhiéu hon.
CH, se oH
CH;—C-ONa + CH;CH;CH)Br “+ CH;—C-OCH,CH,CH,
cH, CHy
8.29. a) Natri etylat tin cong vao C hae hai ft bj cén tré khong gian hon dé
cho stin phdm 1a (E)—2—etoxi—1—metyl—xiclopentanot
cH, 00H,
b) Dudi tac dung cia axit, ancol sé tan edng vao nguyén tit cacbon bac ba
Ai electron hon ctia epoxit dd duge proton héa. San phém 1a (E)—2~etoxi—2—
metylxiclopentanol
OCztg 122
Ancol va phenol
1) BH,,THF, BuLi_
8.30, a) CH)=CH-CHy _ CH,OH-CH-CH,—* ~OCH,CH;CH, (D)
2) H,0,04
| NBS
Bry Kou
CH,=CHCH,Br —+ CH,BrCHBrCH,Br ——» CHBr =CH-CH,Br
i
neo i
(D) + (E) (brom anlylic phan ting) —» (A)
1 Her
—~ CH,CH,MgBr
2) me
b) CH=CH, —— ° CH,CH,CH,CH,OH—
7% CH,(CH,),CH,Br
CH,-CHy .
gH ,c000H a
1,0 Buti (B)
CH,=CHCH, CH,CHOH-CH, —~ (CH,),CHO- —~ (8)
#50, 3 Tor
CH,CH,
) aeene Me og yOHBrCH ye 6,4,CH=CH
° mei, O oS OH TCH am CH= Cle
ea
1) Hg{OCOCF 5),
CHs-CHOHCH, + C,HsCH=CH, ©
8.31.
8.32.
2) NaBhi,
a) Xiclohexylmetanol;
b} 2—-xiclopentylpentanol -2;
¢) 2—metyl-1—phenylpropanol = 1;
a) Metan + 3-hidroxixiclohexanon;
®) 5—phenylnonanol—5,
f) Triphenylmetanol;
g) 1,1-diphenylpropanol-1;
h) 3—(2-hidroxiety})xiclohoxanol;
i) Chi khit xeton, khong khi este;
i) Isobutylaneol;
kd Ancol bac ba;
1) Ancol bac hai;
m) Xiclohexan;
n) (28, 3S) — hexandiol—2,3 + doi quang;
0) (28, 8R) ~ hexandiol-2,3 + déi quang;
p) Heptadien—1,4
a) Hexanol—1, dién tich be mat rong;
b) Hexanol-2, co lién két hidro; Hoa hoc Hau co - Phan Bai tap 123
8.33.
8.34,
8.35,
c} Hexandiol-1,5, hai nhom OH.
a cH, Bi ore
OH
) cys PF é gn
‘Dy Can a) OXY
a) €,H,CHO + CH,CH,MgBr
noac CH,CH,CHO + C,H,MgBr }. A
b) CH,CHO + C,H,CH,MgCl
hoge C,H,CH,CHO + CH,MgBr |. B
co} C,H .CHICH, MgCl + HCHO
>
wd CH,-CH, + C,H.CH,MgCl
27 GH; + CM CH,
So ! =D
hote C,H,CH,CH,MgCl + HCHO
© C,H.CCH, + CH MgBr
oO
oE
hoac (CH,),C=0 + C,H,MgBr
ct nani,
a) C,H, + CH,CH,cocl —*» 6,
He
b) C,H, + HOCH,CH=CH, ——~ C,H,CH,CH=CH, —~
;COCH,CH, ——* A
1) HgiOAcly
pase | CoHsCH,CHOHCH, (B)
2) NaBH,
1) BH, THF
C,H yCH,CH,CH,OH — (D)
2) 1,0,,.04— 124 Ancol va phenol
HF NBS:
©) C,H, + CH,CHOHCH, ——» C,H,CH(CHg); —
00 4Ms
+ CgHsCBr(CH} CHs¢=CH, —
Hy
se CGHACICH, =)
2) Nabi, oye
——] On
1) BH, THE
__*"__.._ €,H,CH(CH;)CH,OH (©)
2) H,0,,.0H ae 9. ANDEHIT VA XETON
K,01,07 °
9.1. a) CH,CH,0H CH,COOH ——- CH,COCH,
3 280, THO,
600° H,80, 328°C
b) CH,;CH, —~- CH,=CH, oy CH,CH,OH — + CH,CHO
°.
Oe 2 es “H,O” CHOCH,CH,CH,CHO
On
CH,CH,COOH —-
d) CH,CH,Br
ote
‘3
soc
——4 cH,CH,cocl —~ CH,CH,cHO
HBr
Mg
e) CH,CH,OH CH,CH,Br —- CH,CH)MgBr
CHyMoBr
KCN
CH,CH,Br —= CH;CH,CN CH,CH,CCH,CH,
°
Ho
Her
0 CH= CH)=CH, ——+ CH,CH,Br
Na CH, CH,Br MgS0,4,80,
CUsCH —- NaC= CH CH,CH,C=CH HyCH,CCH,
AH ing HO
4) e
9.2. =o UA coon SO (ta on]
SGa
NU coon 7 COO
HNO, SzHg0H
0 —* COOH (CH));COOH = CH;COO(CH,),;COOC;Hs =
axit glutaric
Na#C,H,OH HBr KON
seaceat, (CMaIs(OH) —= BriCH,),Br —=— CN(CH,)sCN +
v6—Blang
coo.
H,0 CalOHy “ NF
aaa COOH(CH;};COOH ——=* (CH) Ca
ne
coo’
9.3. Cloral > axetandehit > axeton > dietylxeton > diisopropytxeton. Cloral cho
sin phiim eéng bén véi nitde va véi NH,OH, diisopropylxeton khong fing isopropyl
magie bromua.
9.4. CH,COCH,CH,CHO + 2C,H,OH (HCI khi) = 126 Andehit va xeton
NaOBr
——~ CH,COCH,CH,CHiOC,H,)
2 * oni ha
HCI ladng
——~ HOOCCH,CH,CH(0C;Hs), ———* HOOCCH,CH,CHO
‘hy phan
9.5. (CH,),CHCHOHCH,
9.6. CH,COCH,CH,CHO
9.7. Vinylxiclopentan,
9.8. Su tao thanh monoaxetat chiing to cd mat nhém ancol bac mot hay bac hai;
khong phan ting véi phenylhidrazin ching té nguyén td oxi thd hai khong phai cia
hom cacbonyl. Phan tng véi chi tetraaxetat dé la sy phan hiy glicol thanh hai
nhom cacbonyl; béi vi nhiing nhom cacbonyl nay 6 trong cing mét phan ti (C),
nhom glicol phai la mot bd phan cia vong. Phan ting dusng ctia Felinh chi ra rang
it nhat eo mot nhém eacbonyl 1a andehit, con su tao thanh iodofom cho thay sw
co mat eta nhém metylxeton, Axit adipic HOOCICH,),COOH phai duge tae thanh
ti xetoandehit CH,CO(CH,),CHO can glicol (A) phai cs cau tao sau:
GH CH, OI
CH;-CH,-C-OH SOK
CH)-CH)-CH-OH os
9.9. 0) CH,CH,CH,cHO SL CH,CH,CH,CH,OH—". CH,CH,CH=CH, =
HOH (0)
-—* CH,CH,CHOHCH,——» CH,CH,COCH,
Har NaQH 101
b) CH,CH=CH, ——+ CH,CH,CH)Br CH CH,CH,OH —>
poaxit 3 4,0
CH,CH,CHO
9.10. Nhom cacbonyl etia axit vdi mach eacbon dai nhat phi chia nguyén tu
cacbon tham gia vio nhém xeton. Vi su oxi héa pha hiy eo thé xAy ra & ca hai
phia cia nhom cacbonyl nén trong hén hgp can phai co mot axit chua it hon mot
nguyén tit cacbon so vdi chat trén. Trong tru’ng hop nay dé la cac axit isovalerie
va isobutyric. Vi vay mgt phan cau trie ciia xeton Ia:
ab
R-C-CH,CH(CH3), (deft mach theo "a" cho axit isovaleric, ditt much theo
°
“bt cho isobutyric), cuang ty nhu vay cap axit thit hai cho axit axetic va axit
propionic. Suy ra xeton cé cong thie edu tao:
CH,CH,COCH,CH(CH,),
HyCtO, soc,
9.11, C,H,OH CH,COOH CH,COC! Héa hoc Hau co - Phan Bai tap 127
cH, COC! Zniki ot cocl
CH c,HcocH, >" ¢,H,cH,cH.
NGly Hor
. a 20iH9
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