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Chapter 9 Aromatic compounds 芳香化合物. Text 1: chapter 16, 17 Text 2: 第七章. Contents. 1. The structure of benzene 2. Aromaticity 3. Nomenclature of benzene derivatives 4. Physical properties 5. Reactions of benzene and its derivatives - PowerPoint PPT Presentation
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Chapter 9 Aromatic compounds
芳香化合物
Text 1: chapter 16, 17
Text 2: 第七章
Contents 1. The structure of benzene 2. Aromaticity 3. Nomenclature of benzene derivatives 4. Physical properties 5. Reactions of benzene and its derivatives Electrophilic aromatic substitution ----Effects of s
ubstituents: Reactivity and orientation Nucleophilic aromatic substitution Addition reactions of benzene derivatives Side-chain reactions of benzene derivatives Reactions of phenols
Discovery of Benzene
• Isolated in 1825 by Michael Faraday who determined C:H ratio to be 1:1.
• Synthesized in 1834 by Eilhard Mitscherlich who determined molecular formula to be C6H6.
• Other related compounds with low C:H ratios had a pleasant smell, so they were classified as aromatic( 芳香性的 ).
The Kekule Structure for benzene 苯的克库勒结构
1. The Structure of benzene (16-2, 3)
Proposed in 1866 by Friedrich Kekulé, shortly after multiple bonds were suggested.
Failed to explain existence of only one isomer of 1,2-dichlorobenzene.
orC
CC
C
CC H
H
H
H
H
H
Cl
Cl
Cl
Cl
Same compund
Modern theories of the structure of benzene
RT
Antibonding MO
Bonding MO
·´ ¼ü¹ì µÀ
³É¼ü¹ì µÀ
VB
MO
Hydrogenation of just one double bond in benzene is endothermic (吸热) !
The unusual stability of benzene
Differences in Reactions between alkene and benzene
Br2 / CCl4dark, 25oC
KMnO4 / H2O
25 oC
H2O, HClheat
H2 / Ni
No addition
No hydration
No oxidation
Slow additionat hight temperatureand pressure
Br2 FeBr3
Br
Aromatic Requirements
• Structure must be cyclic with conjugated pi bonds.
• Each atom in the ring must have an unhybridized p orbital.
• The p orbitals must overlap continuously around the ring. (Usually planar structure)
• Compound is more stable than its open-chain counterpart
2. Aromaticity 芳香性
Anti- and Nonaromatic反芳香性和非芳香性
• Antiaromatic (反芳香性的) compounds are cyclic, conjugated, with overlapping p orbitals around the ring, but the energy of the compound is greater than its open-chain counterpart.
• Nonaromatic (非芳香性的) compounds do not have a continuous ring of overlapping p orbitals and may be nonplanar.
Hückel’s Rule (休克尔规则)
• If the compound has a continuous ring of overlapping p orbitals and has 4N + 2 pi electrons, it is aromatic.
• If the compound has a continuous ring of overlapping p orbitals and has 4N electrons, it is antiaromatic.
The (4n+2) pi-Electron Rule
(1) polynuclear aromatic hydrocarbons (PAH, 多核芳烃 ,16-10)
7
8
9
1012
3
4
Phenanthrene·Æ
6
5
2 5
4
10
6
3
78
PyreneÜÅ
1
9
Other aromatic compounds
NaphthaleneÝÁ
12
3
456
78
AnthraceneÝì
12
3
45
6
78 9
10
Fused aromatic compounds 稠环芳烃
As the number of aromatic rings increases, the resonance energy per ring decreases, so larger PAH’s will add Br2.
(mixture of cis and trans isomers)
H Br
H BrH BrH
Br
• [4]Annulene is antiaromatic (4N e-’s)• [8]Annulene would be antiaromatic, but it’s no
t planar, so it’s nonaromatic.• [10]Annulene is aromatic except for the isome
rs that are not planar.• Larger 4N annulenes are not antiaromatic bec
ause they are flexible enough to become nonplanar.
(2) [N]annulenes ( 轮烯 )
HH[10]annulene
nonaromatic
[8]annulene Nonaromatic非芳香性
[18]annulene Aromatic if planar
[16]annulene Antiaromatic if planar
H HHH[14]annulene
nonaromatic
O O
A B
Problem: Which molecule is more stable?
Azulene 奥
(aromatic)
The dipole moment is 1.0D( aromatic 具有芳香性 )
H3C CH3
Answer: (A)
MO Derivation of Hückel’s Rule
• Lowest energy MO has 2 electrons.• Each filled shell has 4 electrons.
=>
The Polygon Rule 多边形规则
ring
Number of πelectrons
π*
π*
nE
Cyclopentadienyl Ions 环戊二烯离子
4 electrons, antiaromatic. 6 electrons, aromatic.
H H
+ OC(CH3)3
H
+ HOC(CH3)3
pKa = 16 pKa = 19
Acidity
Aromatic ions
Tropylium Ion 卓翁离子
6 p electrons and an empty p orbital.
Aromatic: more stable than open chain ion
Cycloheptatrienyl cation环庚三烯阳离子
H OHH+, H2O
H H
Aromatic ions
Dianion of [8]Annulene [8] 轮烯二价阴离子
10 p electrons, aromatic.
Cyclooctatetraenyl dianion环辛四烯二价阴离子
+ 2K + 2K+
Aromatic ions
(3) Heterocyclic aromatic compounds ( 16-9 ) 杂环芳香化合物(中文下册)
N
pyridine吡啶
NH
pyrrole吡咯
O
furan呋喃
S
thiophene噻吩
Pyridine 吡啶
Nonbonding pair of electrons in sp2 orbital, so weak base, pKb = 8.8.
N
Pyrrole 吡咯
Also aromatic, but lone pair of electrons is delocalized, so much weaker base.
NH
Basic or Nonbasic?
NNPyrimidine (嘧啶) has two basicnitrogens.
N N H Imidazole (咪唑) has one basicnitrogen and one nonbasic.
N
N
N
N
H
Purine (嘌呤) ?
=>
3. Nomenclature of benzene derivatives
(1) Monosubstituted benzenes
“XXbenzene” , XX 苯
Fluorobenzene( 氟苯)
Chlorobenzene(氯苯)
Bromobenzene(溴苯)
Nitrobenzene( 硝基苯)
F Cl Br NO2
SO3H COOH COCH3 OCH3
Benzenesulfonic acid苯磺酸
Benzoic acid苯甲酸
Acetophenone苯乙酮
Anisole苯甲醚
CH3 CH2CH3 OH NH2
MethylbenzeneToluene( 甲苯)
Ethylbenzene(乙苯)
HydroxybenzenePhenol(苯酚)
AminobenzeneAniline(氨基苯, 苯胺)
Br BrBr
Br
BrBr
1,3-Dibromobenzenem-Dibromobenzene间二溴苯
1,2-Dibromobenzeneo-Dibromobenzene 邻二溴苯
1,4-Dibromobenzenep-Dibromobenzene对二溴苯
(2) disubstituted benzenes 1,2-; 1,3-; 1,4- o- ( 邻 ), m- ( 间 ), p- ( 对 )
CH3 CH3
CH3
CH3
CH3
CH3
1,2-Dimethylbenzene 1,3-Dimethylbenzne 1,4-Dimethylbenzeneo-xylene m-xylene p-xylene
COOH COOHCOOH
NO2
NO2NO2
2-Nitrobenzoic acid 3-Nitrobenzic acid 4-Nitrobenzic acid
o-Nitrobenzoic acid m-Nitrobenzoic acid p-Nitrobenzoic acid
CH2
Benzyl
CH2Cl
Benzyl chlorideÜлùÂÈÜлù
(3) benzene as substituent: phenyl group ( 苯基 ) , Ph-
CH2CH2CH2CH3 CH3C=CHCH3
Ph
CH3CHCH2CH2CH2CH2CH3
Ph
Butylbenzene 2-Phenyl-2-butene 2-Phenylheptane
Benzyl group ( 苄基 ),Bn-
Aryl group ( 芳基 ),Ar- Arene = Aromatic hydrocarbon
• Melting points: More symmetrical than corresponding alkane, pack better into crystals, so higher melting points.
• Boiling points: Dependent on dipole moment, so ortho > meta > para, for disubstituted benzenes.
• Density: More dense than nonaromatics, less dense than water.
• Solubility: Generally insoluble in water.
4. Physical properties and spectroscopy of aromatic compounds
UV: 254 nm (B 带 )
IR: 3030 (C-H), 1600 (skeleton), 1500 cm-1
1H NMR: 7~9ppm
MS:
m/z, 91
CH2+
+
m/z, 65
+
spectroscopy of aromatic compounds
O
1-phenylpropan-2-one
M+, 134 m/z, 119 m/z, 91
CCH3
O
CO
CH2
m/z, 65
Assignments: T-1: 16-27, 28, 30, 33, 36
Chapter 9 Aromatic compounds
5. Reactions of benzene and its derivatives
(Chapter 17)
Chapter 9 Aromatic compounds
Many benzene and naphthalene( 萘 ) derivatives are useful drugs
阿司匹林,消炎止痛
布洛芬,止痛 沙丁胺醇,
哮喘
对乙酰氨基酚,扑热息痛
萘普生,关节炎 普鲁卡因,
局部麻醉
芬氟拉明,减肥
1) Electrophilic aromatic substitution reactions
17-2
17-3
17-4
17-10
17-11
X2, FeX3
(X = Cl, Br)
X+ HX
Halogenation±»¯
NO2HNO3
H2SO4 + H2O
SO3
H2SO4
SO3H
RCl, AlCl3 R+ HCl
RCOCl, AlCl3 R
O
Nitration Ïõ »¯
Sulfonation»Ç»¯
Friedel-Crafts Alkylation傅-¿ËÍé »ù»¯
Friedel-Crafts Acylation傅-¿Ëõ£»ù»¯+ HCl
Electrophilic addition-elimination mechanism亲电加成 - 消除机理
Arenium ion ( 芳基正离子 ) intermediateσ- complex (σ- 络合物)
+ E+
E
H
+ E
H+
E
H+
Step 1: addition
Step 2: elimination
E
H
+
+ H+
E
E
H+
Eact1
Eact2
TS 1
TS 2
E
reaction coordination
The reaction-energy diagram ( 反应能线图 )
rate-limiting step
reactants
σ-complex
product
Halogenation of benzene: X2, FeX3
Reactivity: F2 > Cl2 > Br2 > I2
Br Br FeBr3
+ BrH
+ Br
H+
Br
H++ FeBr4
Br Br + FeBr3 Br Br FeBr3
+
+ I2I
HNO3
86%
+ + NO2 + H2O
BrH
+ Br
+ H[FeBr4]
FeBr4FeBr3 + HBr
I2 + 2HNO3 + 2H+ 2I+ + 2NO2 + 2 H2O
Nitration of benzene: HNO3 + H2SO4
H O N
OO H O S
O
O
O H+ H O N
OO
H+ HSO4
O N O + H2O
Nitronium ionsrong electrophile
ON
O NH
O
ON
H
O
ON
H
O
O
NH
O
ON
O
ONO2
Sulfonation of benzene: fuming sulfuric acid ( 发烟硫酸 ) 7% SO3 in H2SO4
SO
O
OS
O
O
OS
O
O OS
O O
O
SO
O
O+
SH O
O
OH
SO3H
SO3H+ H2O + H2SO4heat
The Friedel-Crafts alkylation of benzene: RX, AlCl3( or ether Lewis acid)
R······X······AlCl3δ+ δ-
E+:
R+ can rearrangement; Polyalkylations often occur.
C=C, H+
C-C-OH, acid
Other carbocation source
Limitations:
Problems:
Predict products for the reactions of benzene with the fol
lowing reagents.
Cl
Cl
+ HF
OH + BF3
(a)
(b)
(c)
(d)
+ AlCl3
+ AlCl3
The Friedel-Crafts Acylation of benzene:
RCOCl, AlCl3 (Lewis acid)
E+:
R O R
O O
Acylium ion 酰基正离子
RC
OC
R
O O AlCl3
RC
O
OC
R
O AlCl3
RC
Cl
O
AlCl3 RC
O
Cl AlCl3
RC
O
RC
O
The Gatterman-Koch formylation:——synthesis of genzaldehyde
AlCl3/CuClC H
O
+ CO + HCl
CO + HClH C Cl
O
The Clemmensen reduction: ——synthesis of alkylbenzenes.
RCOCl, AlCl3C R
O
aq HCl
Zn[Hg]CH2 R
The Clemmensen reduction
CH2CH2CH3
How to shnthesize n-propylbenzene from benzene?
CCH2CH3
O
S
o-
m-
p-(1) Reactivity: Electron donating group ( 给电子 ): Activiting ( 活化 ) Electron withdrawing ( 拉电子 ): deactivating ( 钝化 )(2) Orientation: o-, m-, p-, which is major?
The effects of substituents on the electrophilic aromatic substitution:
Reactivity and Orientation
CH3 CH3 CH3 CH3
+ +HNO3
H2SO4
NO2
NO2
NO2
H
H
H
H
H
Yield: 60% 4% 36%
Nitration of toluene
Why?
Toluene is about 25 times faster than benzene.
A) Activating groups: ortho-para directors活化,邻、对位定位基
-O-, -NR2, HO-, RO-, CH3CONH-, R-
( 和芳环碳相连的原子带部分负电荷 , 或有孤对电子 , 因 ) 此有给电子作用 .)
17-6
Alkyl groups, substituents with nonbonding electrons (O, N) can activate the aromatic ring.
OH
+ 3Br2H2O
OH
BrBr
Br
+ 3 HBr
B) Deactivating groups: Meta-Directors钝化,间位定位基
-+NR3, -NO2, -CF3, -CCl3, -CN, -SO3H, -CHO, RCO-, -COOH, -COOR, CH3CO-,
NO2
HNO3
H2SO4
NO2
NO2
NO2
NO2
+ +
6% 1% 93%
NO2
NO2
( 和芳环碳相连的原子带部分正电荷 , 因此有拉电子作用 .)
17-7
In general, deactivating substituents are groups with a positive charge (or a partial positive charge) on the atom bonded to the aromatic ring.
C) Halo substituents: Deactivating but ortho-para directors ( 卤代:钝化 , 但是邻对位定位基 )
Cl
HNO3
H2SO4
Cl
NO2
Cl
NO2
+
30% 70%
Cl
Cl
Cl
Cl
+
39% 55%
Cl2FeCl3
+
Cl
Cl
6%
Cl
17-8
Halo substitution: electron withdrawing groups, 吸电子基
Inductive effect explanation 诱导效应解释
S
E+
¦Ä+
¦Ä-
¦Ä-¦Ä+
S
E+¦Ä+
¦Ä-
¦Ä-
¦Ä+
Explanation of the orientaion
Resonance effect explanation共振效应解释
NH2 OH OCH3 Cl
Aniline Phenol Chlorobenzeneanisole
CH3
toluene
m- director
o-, p- director
CF3 NO O
Conclusion:-CF3 is a m-director 。
+ charges adjacent,unstable
o-
p-
m-
HE
CF3H
E
CF3H
E
CF3
HE
CF3
HE
CF3
HE
CF3
CF3
E
H
CF3
E
H
CF3
E
H
δ+
δ+
N
EH
N
EH
N
EH
O O OO O O
HE
N
HE
N
HE
NO O OO O O
H E
NH E
NH E
NO O O O O O
o-
p-
m-
Conclusion:-NO2 is a m-director 。
+ charges adjacent,unstable
Conclusion:-CH3 is a o- and p-director.
3°favorable
3°favorable
o-
p-
m-
HE
CH3H
E
CH3H
E
CH3
HE
CH3
HE
CH3
HE
CH3
CH3
E
H
CH3
E
H
CH3
E
H
o-
p-
m-
HE
OHH
E
OHH
E
OHH
E
OH
HE
OH
HE
OH
HE
OH
HE
OH
OH
E
H
OH
E
H
OH
E
H
Conclusion:-OH is a o- and p-director.
Especially stable
o-
p-
m-
HE
ClH
E
ClH
E
ClH
E
Cl
HE
Cl
HE
Cl
HE
Cl
HE
Cl
Cl
E
H
Cl
E
H
Cl
E
H
Conclusion:-Cl is a o- and p-director.
Especially stable
Notice: Friedel-Crafts reactions fail with strongly deactivated systems.
NH2
+ AlCl3
(-NHR, -NR2) NH2
+Cl3Al
OH
+ AlCl3
OH+
Cl3Al(OR)
Aniline and phenol (especialy aniline )does not undergo a Friedel-Crafts reaction
Orientation in disubstituted benzenes
两个取代基定位效应一致—共同指向位置
两个取代基定位效应不一致—由邻对位基确定指向位置 ; 如两个都是间位或邻对位定位基,由强者确定指向位置。
NHCOCH3
SO3H
CF3
NO2
OH
NO2
NHCOCH3
HO3S
CF3
NO2
OH NO2
biphenyl联苯
2) Nucleophilic aromatic substitution
Substrate: aryl halide ( 芳基卤 )Cl
NO2
OHNO2
+ OH- aq. NaHCO3
130CH+
ClNO2
NO2
OHNO2
NO2
+ OH- aq. NaHCO3
100CH+
ClNO2
NO2
O2NOH
NO2
NO2
O2N+ OH-
aq. NaHCO3
35C
H+
邻、对位有吸电子基有利。
Addition-elimination mechanismCl
NO2
+ OH- additionslow
OHCl
NO2
eliminationfast
OH-+ Cl-
O-
NO2
OH
NO2
+ Cl-
Cl
350¡æ(high pressure)
ONaNaOH HCl
OH
Br
K+NH2- NH2
-
NH3
NH2
NH2
(50%)
(50%)
14 14
14
14
Elimination-addition mechanism: benzyne 苯炔机理
base = NaNH2
or high pressure
3) Addition reactions of benzene derivatives
(1) Chlorination
ClCl
Cl
ClCl
Cl
Cl2hv
or high T, pFree radical mechanism
(2) Addition of hydrogen (reduction)
H2
catalystcatalyst: Pt, Pd, Ru, Rh, Ni
No
The Birch reduction 伯奇还原
Developed by the Australian chemist A.J. Birch
Benzene
NH3, EtOH
1,4-Cyclohexadiene
Na or K
Mechanism: similar as trans- reduction of alkyne with Na/NH3(liq.) (p-756)
1,2-Dimethylbenzene
NH3, EtOH
NaCH3 CH3
1,2-Dimethyl-1,4-cyclohexadiene 77-92 %
CH3 CH3
(o-xylene)
Methoxybenzene±½¼×ÃÑ
NH3, EtOH
LiOCH3 OCH3
1-Methoxy-1,4-cyclohexadiene 80 %
Sodium benzoate
NH3, EtOH
Na
(±½¼×ËáÄÆ)
COONa COONa
H3O+
COOH
89-52 %
electron donating给电子基,氢加在 2,5- 位
electron withdrawing拉电子基 , 氢加在 1,4- 位
4) Reactions of the side chain of alkylbenzenes
(1) Halogenation of the side chain benzylic radicals
useful in synthesis
Notice: 氯代产物复杂,除苄基位外还有 β 位取代产物。
hvCCl4
CH2Br
Benzyl bromide 64%
CH3
+ NBr
NBS
+ NH
Toluene
O
O
O
O
hv, CCl4
CHBr
CH2CH3NBS
CH3
(2) Oxidation of the side chain
The alkyl side chain with α - H on a benzene ring is oxi
dized to benzoic acid by chromic acid( 铬酸 ) or KMnO4.
CH2CH2CH3
1) KMnO4, OH-
2) H3O+
COOH
Benzoic acid 100% CH2CH2CH3
1) KMnO4, OH-
2) H3O+
C(CH3)3
COOH
C(CH3)3
+ O2
V2O5
450~500 °CO
O
O
5) phenols (17-15)
OH
OH
OH
OH
HO OH
1,2-Benzenediol(¶ù²è·Ó,ÁÚ±½¶þ·Ó)
1,3-Benzenediol(À×Ëö·Ó,¼ä±½¶þ·Ó£©
1,4-Benzenediol (¶Ô±½¶þ·Ó)
CH3
OH
CH3
OH
H3C OH
2-Methylphenol(ÁÚ-¼×·Ó£©
3-Methylphenol(¼ä-¼×·Ó£©
4-Methylphenol(¶Ô-¼×·Ó£©
Synthesis of phenol
in laboratory Ar-NH2
HONO Ar-N2+ H3O+
heat Ar-OH
Cl
350¡æ(high pressure)
ONaNaOH HCl
OH
industrial synthesis
Oxidization:
+ O295-135¡æ O O H Cumene hydroperoxide
(¹ý Ñõ» Ò̄ì±û»ù±½)
Hydrolytic rearrangement:
O O H H+, H2O
50-90¡æOH
O
+Acetone (±ûͪ £©
ArOHNaOH ArO-Na+ R-X
X = Cl, Br, I, OSO2R' or ,OSO2OR.
ArOR + NaX
Aspirin 阿斯匹林
Reactions of phenols
OH
COOHOCCH3
COOH
+ H+
O
+ CH3COOH
Salicylic acid (Ë®ÑîËᣩ
Acetic anhydride (ÒÒËáôû£©
Axetylsalicylic acid (ÒÒõ£Ë®ÑîËᣩ
(CH3CO)2O
A) Acidity
B) Acylation of hydroxyl group
White precipitate.
C) Electrophilic aromatic substitution
OH
+ 3Br2H2O
OH
BrBr
Br
+ 3 HBr
2,4,6-Tribromophenol (2,4,6-Èýäå±½·Ó£©
OH
+ Br2CCl4
OH
Br
+ HBr
OH
Br
+
OH
OH
OH
SO3H
SO3H
concdH2SO4
25¡æ
100¡æ
concd H2SO4, 100¡æ
equilibrium control
rate control
The o- and p- nitrophenol can be separated by steam distillation( 不蒸汽蒸馏 ).
OH OH OH
NO2
NO2
20% HNO3
25¡æ+
(30 - 40 %) (15 %)
D) Oxidation of phenols
OH O
O
K2Cr2O7-H2SO4
Notice: 在合成中酚羟基通常要保护,以防止氧化
p-Benzoquinone ( 对 - 苯醌 )
E) Reaction with FeCl3
phenol , 蓝紫色,烯醇的特殊性质。用来检验酚或烯醇结构。
6) Naphthalene 萘
αα
α α
β
β
β
β
1
2
3
45
6
7
89
10
NO2 SO3H
CH3
0.142 0.136
0.1400.139
1-nitronaphthaleneα-nitronaphthalene
5-methyl-2-naphthalenesulfonic acid5-methyl- β -naphthalenesulfonic acid
Reactions of naphthalene
Reactivity: naphthalene > benzene α- >β-
A) Substitution
+ Br2
CCl4
Br
H2SO4
SO3H
~60°C
> 150°C SO3H
84%
85%
equilibrium control
rate control
Notice: 一取代萘的定位效应也受环上原有取代基的控制。
+ CH3CCl
OAlCl3
CS2
CO CH3
+ CH3CCl
OAlCl3
PhNO2
C
O
CH3
CH3 CH3 NO2
B) Oxidation and reduction
O
O
CrO3, HOAc
O
O
CrO3, HOAcCH3 CH3
V2O5
400°CO
O
O
1,4-dihydronaphthalene1,4- 二氢萘
decalin十氢萘
C2H5OH
Na , NH3(l)
H H
H H
C2H5OH
Na , NH3(l)
H H
H H
OCH3OCH3
Pt, H2
high P, heating
Summary1. 理解苯分子的结构,并能用 RT , VB , MO 法解释其特
殊稳定性的原因。2. 会用 Hückel rule 判断环状共轭体系是否具有芳香性。3. 会命名苯的衍生物,苯作为母体或作为取代基。4. 熟悉苯的波谱特征。5. 熟练掌握苯及其衍生物的亲电芳香取代反应的历程、定
位规则,掌握卤代、硝化、磺化、 Fridel-Crafts 烷基化及酰基化反应,并能用于苯衍生物的合成。
6. 掌握苯的侧链反应特点:氧化、自由基卤代及其在有机合成中的应用。
7. 掌握苯酚的反应特点:羟基的反应、芳环上的反应。8. 了解苯的加成反应,尤其是催化加氢和 Berch reduction
反应的特点与机理。9. 了解卤代苯的亲核取代反应、萘的反应特点。
CH2CH2CH2CH3
O
Problems
How to synthesis the following compounds?
先酰化,再还原。
O
O
O
先酰化 - 还原 - 酰氯 - 酰化
NH2 NH2
NO2
and
NH2
NO2
NO2
Cl CH2CH2CH3
CH3CH2Br
Br
上官能团顺序:丙酰化-氯化-硝化
不能在酸性条件下直接硝化。应先把氨基酰化后再硝化。
磺酰化-溴化-自由基溴化苄基位
O
CH3
AlCl3+ C9H12O
Propose mechanism and predict the structure of the product.
Assignments
• T-1: 17-44, 46, 47, 49, 50, 51,
• 57,59, 61, 65
• T-2 ( selected ) : 5, 6, 7, 11, 12, 18, 19
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