Chapter 17 ArReaction

Chapter 17 Reactions of Aromatic
Compounds
© 2017 Pearson Education, Ltd. Lecture 芳香族化合物的反應
© 2014 Pearson Education, Inc.
17-1 Electrophilic Aromatic Substitution (EAS)
• Although benzene’s pi electrons are in a stable aromatic system, they

are available to attack a strong electrophile to give a carbocation.
儘管苯的π電⼦處於穩定的芳香體系中，但是它們可以攻擊強親
電⼦體以產⽣碳陽離⼦。
• This resonance-stabilized carbocation is called a sigma complex
because the electrophile is joined to the benzene ring by a new sigma
bond.
這種共振穩定的碳陽離⼦被稱為σ複合物，因為親電試劑通過新
的σ鍵連接到苯環上。
• Aromaticity is regained by loss of a proton.
芳香性通過質⼦的喪失⽽恢復
© 2017 Pearson Education, Ltd.

Mechanism of Electrophilic Aromatic Substitution
Step 1: Attack on the electrophile forms the sigma complex.
步驟 1：攻擊親電⼦試劑形成σ複合物。
Step 2: Loss of a proton gives the substitution product.

步驟 2：質⼦的損失產⽣了替代產物

17-2 Halogenation of Benzene
Bromination of Benzene
苯的溴化反應

Mechanism for the Bromination of Benzene: Steps 1 and 2
Step 1: Electrophilic attack and formation of the sigma comple
步驟 1：親電攻擊和σ複合物的形成
Step 2: Loss of a proton to give the products

步驟 2 ：失去⼀個質⼦給產物

Chlorination of Benzene
苯的氯化
• Chlorination is similar to bromination. AlCl3 is most often

used as catalyst, but FeCl3 will also work.
氯化與溴化相似。三氯化鋁最常⽤作催化劑，但三氯
化鐵也起作⽤。

Iodination of Benzene
苯的碘化
• Iodination requires an acidic oxidizing agent, like nitric

acid, to produce iodide cation.
碘化需要酸性氧化劑，如硝酸，⽣成碘化物陽離⼦。
H+ + HNO3 + ½ I2 I+ + NO2 +
H2O

Mechanism for the Bromination of Benzene:
Preliminary Step 苯溴化機理的初步探討
• Before the electrophilic aromatic substitution can take place,

the electrophile must be activated.
在發⽣親電⼦芳族取代之前，親電⼦試劑必須被激活。
• A strong Lewis acid catalyst, such as FeBr3, should be used.
應使⽤強烈的路易斯酸催化劑，如FeBr3

17-3 Nitration of Benzene 苯的硝化
• Sulfuric acid acts as a catalyst, allowing the reaction to be

faster and at lower temperatures.
硫酸作為催化劑，使反應更快，溫度更低。
• HNO3 and H2SO4 react together to form the electrophile of
the reaction: nitronium ion (NO2+).
HNO3和H2SO4反應⽣成硝酸根離⼦（NO2 +）。

Mechanism for the Nitration of Benzene: Preliminary Step
苯硝化機理的初步研究
• Formation of the nitronium ion is the preliminary step

of the reaction.
硝酸根離⼦的形成是反應的預備步驟。

Mechanism for the EAS Nitration of Benzene
苯的EAS硝化機理
Step 1: Formation of the sigma complex
步驟 1：形成sigma複合體
Step 2: Loss of a proton gives nitrobenzene.

步驟 2：質⼦的損失產⽣硝基苯

Reduction of the Nitro Group
還原硝基基團
• Treatment with zinc, tin, or iron in dilute acid will reduce

the nitro to an amino group.
在稀酸中⽤鋅，錫或鐵處理會將硝基還原為氨基。
• This is the best method for adding an amino group to the
ring.
這是向環上添加氨基的最佳⽅法。

17-4 Sulfonation of Benzene 苯的磺化
• Sulfur trioxide (SO3) is the electrophile in the reaction.

三氧化硫(SO3)是反應中的親電⼦試劑。
• A 7% mixture of SO3 and H2SO4 is commonly referred to as
“fuming sulfuric acid.”
SO3和H2SO4的7％混合物通常被稱為“發煙硫酸”。
• The —SO3H group is called a sulfonic acid.
SO3基團被稱為磺酸

Mechanism of Sulfonation
• Benzene attacks sulfur trioxide, forming a sigma complex.

苯攻擊三氧化硫，形成sigma複合體
• Loss of a proton on the tetrahedral carbon and reprotonation of oxygen
gives benzenesulfonic acid.
四⾯體碳上的質⼦的損失和氧的重新氫化產⽣苯磺酸。
Desulfonation Reaction
脫磺化反應
• Sulfonation is reversible.
磺化是可逆的
• The sulfonic acid group may be removed from an aromatic
ring by heating in dilute sulfuric acid.
磺酸基團可以通過在稀硫酸中加熱⽽從芳環中除去。

Mechanism of Desulfonation
• In the desulfonation reaction, a proton adds to the ring (the

electrophile) and loss of sulfur trioxide gives back benzene.
在脫磺化反應中，質⼦加到環（親電試劑）上，三氧化
硫的損失使苯回流。

Hydrogen–Deuterium Exchange
• The reaction is proven by using a deuterium ion (D+) rather than

a proton and by showing that the product contains a deuterium
atom in place of hydrogen.
通過使⽤氘離⼦(D+)⽽不是質⼦來證明該反應，並且通
過顯⽰該產物含有氘原⼦代替氫。
© 2017 Pearson Education, Ltd. Problem 3, 4, 64, 66, 77
Problem 66

17-5 Nitration of Toluene: The Effect of Alkyl Substitution
甲苯硝化反應：烷基取代反應的影響
• Toluene reacts 25 times faster than benzene.

甲苯反應比苯快25倍。
• The methyl group is an activator.
甲基是⼀種活化劑
• The product mix contains mostly ortho- and para-
substituted molecules.
產物混合物主要含有鄰位和對位取代的分⼦。
Substitution

Ortho and Para Substitution
• Ortho and para attacks are preferred because their resonance

structures include one tertiary carbocation.
鄰位和對位攻擊是優選的，因為它們的共振結構包括⼀個三級
碳陽離⼦。
Meta Substitution
• When substitution occurs at the meta position, the positive charge is

not delocalized onto the tertiary carbon, and the methyl group has a
smaller effect on the stability of the sigma complex.
當在間位發⽣取代時，正電荷不會在叔碳上離域，⽽甲基對σ配
合
物的穩定性影響較⼩。當在間位發⽣取代時，正電荷不會在叔碳
上離域，⽽甲基對σ配合物的穩定性影響較⼩。

17-6 Activating, O-, P-Directing Substituents
Alkyl Group Stabilization
• Alkyl groups are activating substituents and ortho,

para-directors.
烷基是活化取代基和鄰位，π-對 - 導向物。
• This effect is called the inductive effect because alkyl groups can
donate electron density to the ring through the sigma bond, making
them more active.
這種效應被稱為誘導效應，因為烷基可以通過σ鍵給環提供電⼦
密度，使它們更加活躍。.
Anisole
• Anisole undergoes nitration about 10,000 times faster than benzene

and about 400 times faster than toluene.
茴香醚比苯快硝化約10000倍，比甲苯快約400倍。
• This result seems curious because oxygen is a strongly electronegative
group, yet it donates electron density to stabilize the transition state
and the sigma complex.
這個結果似乎是好奇的，因為氧是⼀個強負電基團，但是它提供
了電⼦密度來穩定過渡態和σ複合物。
Substituents with Nonbonding Electrons
非鍵電⼦的取代基
Resonance stabilization is provided by a pi bond between the

—OCH3 substituent and the ring.
通過—OCH3取代基與環之間的π鍵提供共振穩定性。

Meta Attack on Anisole
• Resonance forms show that the methoxy group cannot

stabilize the sigma complex in the meta substitution.
共振形式表明甲氧基團不能穩定σ取代中的σ絡合物

Bromination of Anisole
茴香醚的溴化
• A methoxy group is so strongly activating that anisole is

quickly tribrominated without a catalyst.
甲氧基的活化非常強烈，因此苯甲醚在沒有催化劑的
情況下被快速溴化。

The Amino Group
• Aniline reacts with bromine water (without a catalyst) to

yield the tribromoaniline.
苯胺與溴⽔反應（不含催化劑）產⽣三溴苯胺。
• Sodium bicarbonate is added to neutralize the HBr that is
also formed.
加入碳酸氫鈉以中和也形成的HBr。

The Amino Group, EAS Reaction
Problem 12

Nitration of Nitrobenzene
• Electrophilic substitution reactions for nitrobenzene are 100,000

times slower than for benzene.
硝基苯的親電取代反應比苯的慢10萬倍。
• The product mix contains mostly the meta isomer and only small
amounts of the ortho and para isomers.
產物混合物主要含有間位異構體，只有少量鄰位和對位異構體。

Ortho Substitution of Nitrobenzene
• The nitro group is a strongly deactivating group when considering its

resonance forms. The nitrogen always has a formal positive charge.
考慮到它的共振形式，硝基是⼀個強烈的失活基團。氮總是有正
式的正電荷。
• Ortho or para addition will create an especially unstable intermediate.
鄰位或對位添加會造成特別不穩定的中間體。

Meta Substitution on Nitrobenzene
對硝基苯的間位取代
• Meta substitution will not put the positive charge on the

same carbon that bears the nitro group.
間位取代取代不會把正電荷放在同⼀個帶有硝基的碳
上。

Para Substitution on Nitrobenzene
硝基苯的對位取代反應
• Para substitution will place the positive charge on the

same carbon that bears the nitro group.
對位取代會將正電荷置於攜帶硝基的同⼀碳上。

Deactivators and Meta-Directors
去活化者和臨位
• Most electron-withdrawing groups are deactivators and
meta-directors.
⼤多數吸電⼦團體是失活者和間位。
• The atom attached to the aromatic ring has a positive or
partial positive charge.
連接在芳環上的原⼦有正或負的正電荷。
• Electron density is withdrawn inductively along the sigma
bond, so the ring has less electron density than benzene, and
thus it will be slower to react.
電⼦密度沿著σ鍵感應取消，因此環的電⼦密度比苯⼩
，因此反應速度會慢⼀些。
Ortho Attack of Acetophenone
• In ortho and para substitution of acetophenone, one of the carbon

atoms bearing the positive charge is the carbon attached to the partial
positive carbonyl carbon.
在苯⼄酮的鄰位和對位取代中，攜帶正電荷的碳原⼦之⼀是連接
到部分正羰基碳上的碳。
• Since like charges repel, this close proximity of the two positive
charges is especially unstable.
由於類似的電荷排斥，這兩個正電荷的接近是特別不穩定的。
Meta Attack on Acetophenone
• The meta attack on acetophenone avoids bearing the

positive charge on the carbon attached to the partial
positive carbonyl.
對苯⼄酮的間接攻擊避免了附著在部分正羰基上的
碳帶正電荷。

Other Deactivators

17-8 Halogen Substitutions: Deactivating, but Ortho, para-
Directing
Halogens
• Halogens are deactivators since they react slower than

benzene.
⿄素是鈍化劑，因為它們反應比苯慢。
• Halogens are ortho, para-directors because the halogen can
stabilize the sigma complex.
⿄素是鄰位，對位導電因為⿄素可以穩定σ配合物。
Halogens Are Ortho, Para-Directors
• Resonance effect: The lone pairs on the halogen can be

used to stabilize the sigma complex by resonance.
共振效應：⿄素上的孤對可⽤於通過共振來穩定σ複合
物。

Halogens Are Deactivators
• Inductive effect: Halogens are deactivating because they

are electronegative and can withdraw electron density from
the ring along the sigma bond.
誘導效應：⿄素由於具有負電性⽽可以失活，並且可以
沿
著σ鍵從環上撤回電⼦密度。

Summary of Directing Effects

17-9 Effect of Multiple Substituents on Electrophilic
Aromatic Substitution
• The position in between two groups in positions 1 and 3 is

hindered for substitution, and it is less reactive.
位置1和位置3兩組之間的位置被阻礙替代，並且反
應性較⼩。

Effect of Multiple Substituents
多取代基的影響
• The directing effect of the two (or more) groups may

reinforce each other.
兩個（或更多）組的指揮效果可能相互加強。

Effect of Multiple Substituents
多取代基的影響
• If directing effects oppose each other, the most powerful

activating group has the dominant influence.
如果指揮效果相互對立，最強⼤的激活群體占主導地
位。

Solved Problem 1
Predict the major product(s) of bromination of p-chloroacetanilide.
Solution
The amide group (–NHCOCH3) is a strong activating and directing group because the nitrogen atom
with its nonbonding pair of electrons is bonded to the aromatic ring. The amide group is a stronger
director than the chlorine atom, and substitution occurs mostly at the positions ortho to the amide. Like
an alkoxyl group, the amide is a particularly strong activating group, and the reaction gives some of the
dibrominated product.
Problem 13, 14, 43, 44, 46

Solved Problem 1
Predict the major product(s) of bromination of p-chloroacetanilide.
Solution
The amide group (–NHCOCH3) is a strong activating and directing group because the nitrogen atom
with its nonbonding pair of electrons is bonded to the aromatic ring. The amide group is a stronger
director than the chlorine atom, and substitution occurs mostly at the positions ortho to the amide. Like
an alkoxyl group, the amide is a particularly strong activating group, and the reaction gives some of the
dibrominated product.
Problem 13, 14, 43, 44, 46

17-10 Friedel-Crafts Alkylation
• Synthesis of alkyl benzenes from alkyl halides and a Lewis

acid, usually AlCl3
由⿄代烷和路易斯酸（通常為AlCl3）合成烷基苯
• Reactions of alkyl halide with Lewis acid produce a
carbocation, which is the electrophile.
烷基⿄與路易斯酸的反應產⽣碳陽離⼦，其為親電試
劑。

Mechanism of the Friedel–Crafts Reaction
Step 1:
Step 2:
Step 3:

Problem 15
Protonation of Alkenes
• An alkene can be protonated by HF.

烯烴可以被HF質⼦化
• This weak acid is preferred because the fluoride ion is a
weak nucleophile and will not attack the carbocation.
這種弱酸是優選的，因為氟離⼦是弱親核試劑，不會攻
擊碳陽離⼦。
Alcohols and Lewis Acids 醇和路易斯酸
• Alcohols can be treated with BF3 to form the carbocation.

• 醇可以⽤BF 3處理以形成碳陽離⼦。

Problem 16
Limitations of Friedel–Crafts
Friedel-Crafts的限制
• Reaction fails if benzene has a substituent that is more
deactivating than halogens.
如果苯具有比⿄素更失活的取代基，則反應失敗。
• Rearrangements are possible.
重新排列是可能的。
• The alkylbenzene product is more reactive than benzene,
so polyalkylation occurs.
烷基苯產物比苯更具活性，所以發⽣多烷基化。

Rearrangements

Multiple Alkylations
© 2017 Pearson Education, Ltd. Problem 17, 19, 45, 46, 47, 48, 49
17-11 Friedel-Crafts Acylation
• Acyl chloride is used in place of alkyl chloride.

使⽤醯氯代替烷基氯。
• The product is a phenyl ketone that is less reactive than
benzene.
該產物是⼀種比苯反應性低的苯基酮。
Mechanism of Acylation
Step 1: Formation of the acylium ion

步驟 1：形成酰基離⼦
Step 2: Electrophilic attack to form the sigma complex

步驟 2：親電攻擊以形成σ複合物

Mechanism of Acylation
Step 3: Loss of a proton to form the product
步驟 3：失去⼀個質⼦形成產品

Clemmensen Reduction
• The Clemmensen reduction is a way to convert

acylbenzenes to alkylbenzenes by treatment with aqueous
HCl and amalgamated zinc.
Clemmensen還原是⼀種通過⽤HCl⽔溶液和汞⿑化鋅
處理將酰基苯轉化為烷基苯的⽅法。

Gatterman–Koch Formylation
• A formyl group cannot add to benzene via Friedel–Crafts

acylation in the usual manner.
甲酰基不能以通常的⽅式通過Friedel-Crafts酰化作⽤加
到苯中。
Problem 20, 21, 50
Prob. 21

Benzyne Reaction: Elimination–Addition
• Reactant is halobenzene with no electron-withdrawing

groups on the ring.
反應物是⿄代苯，環上沒有吸電⼦基團。
• Use a very strong base like NaNH2.
使⽤⼀個非常強⼤的鹼，如NaNH2。

Benzyne Mechanism
• Sodium amide abstracts a proton.

氨基鈉提取質⼦。
• The benzyne intermediate forms when the bromide is expelled and the
electrons on the sp2 orbital adjacent to it overlap with the empty sp2
orbital of the carbon that lost the bromide.
當溴化物被排出時，芐基中間體形成，並且與其相鄰的sp2軌道上
的電⼦與失去溴化物的碳的空sp2軌道重疊。
• Benzynes are very reactive species due to the high strain of the triple
bond.
由於三鍵的⾼應變，芐基是非常活潑的物質。
Nucleophilic Substitution on the Benzyne Intermediate

17-12 Nucleophilic Aromatic Substitution
• A nucleophile replaces a leaving group on the aromatic

ring.
親核試劑取代芳環上的離去基團。
• This is an addition–elimination reaction.
這是加成消除反應。
• Electron-withdrawing substituents activate the ring for
nucleophilic substitution.
吸電⼦取代基激活環進⾏親核取代。
Mechanism of Nucleophilic Aromatic Substitution
Step 1: Attack by hydroxide gives a resonance-stabilized complex
步驟1：氫氧化物的攻擊產⽣共振穩定的複合物。.
Step 2: Loss of chloride gives the product Step 3: Excess base deprotonates the product
第2步：失去氯化物產⽣的產物。. 步驟3：多餘的鹼使產物去質⼦化.
Problem 23, 24, 58, 68, 73

17-13 Aromatic Substitution Using Organometallic
Reagent
• Friedel–Craft reactions have limitations.
– Rearrangements 重排
– Multiple alkylations 多重烷基化
– Cannot occur on deactivated rings
不能在停⽤的環上發⽣
– Need strong electrophiles
需要強⼤的親電⼦
• Organometallic reagents can add alkyl groups to the
benzene without these limitations.
有機⾦屬試劑可以將苯基添加到苯中⽽沒有這些限制。
Organocuprate Reagents
R—X + 2 Li R—Li + LiX
2 R—Li + CuX R2CuX + LiX
• Lithium dialkylcuprate reagents (Gilman reagents) can be

prepared by reaction of two equivalents of an
organolithium reagent with cuprous iodide.
⼆烷基亞磷酸鋰試劑（Gilman試劑）可以通過使兩當
量的有機鋰試劑與碘化亞銅反應來製備。

Coupling Using Organocuprate Reagents
• Mechanisms vary depending on the alkyl halide and

organocuprate used.
機理根據使⽤的烷基⿄化物和有機銅酸鹽⽽變化。
• It cannot be SN2 because vinyl and aryl halides work well
in this reaction.
它不能是SN2，因為⼄烯基和芳基⿄化物在這個反應中
很好地⼯作。 Problem 25, 26
17-14 Addition Reactions of Benzene Derivatives
Chlorination of Benzene
• Addition to the benzene ring may occur with excess of

chlorine under heat and pressure.
在加熱和加壓條件下，加入過量的氯可能導致苯環的
加入。
• The first Cl2 addition is difficult, but the next two moles
add rapidly.
• 第⼀次添加Cl2很困難，但接下來的兩次增加很快。
Catalytic Hydrogenation
• Elevated heat and pressure are required.

需要升⾼的熱量和壓⼒。
• Possible catalysts: Pt, Pd, Ni, Ru, Rh
可能的催化劑：Pt，Pd，Ni，Ru，Rh
• Reduction cannot be stopped at an intermediate stage.
在中間階段不能停⽌減排。
Birch Reduction
• This reaction reduces the aromatic ring to a nonconjugated

1,4-cyclohexadiene.
該反應將芳香環還原成非共軛的1,4-環⼰⼆烯。
• The reducing agent is sodium or lithium in a mixture of
liquid ammonia and alcohol.
還原劑是在液氨和醇的混合物中的鈉或鋰。
Mechanism of the Birch Reduction

Limitations of the Birch Reduction
Problem 59, 74
17-15 Side-Chain Reactions of Benzene Derivatives
Side-Chain Oxidation
• Alkylbenzenes are oxidized to benzoic acid by heating in basic

KMnO4 or heating in Na2Cr2O7/H2SO4.
通過在鹼性KMnO4中加熱或在Na2Cr2O7/H2SO4中加熱將烷基
苯氧化為苯甲酸。。
• The benzylic carbon will be oxidized to the
carboxylic acid.
苯甲基碳將被氧化成羧酸。
Side-Chain Halogenation
• The benzylic position is the most reactive.

benzylic位置是最活躍的。
• Br2 reacts only at the benzylic position.
Br2僅在芐基位置上反應
• Cl2 is not as selective as bromination, so this results in
mixtures.
Cl2不像溴化那樣具有選擇性，所以這導致混合物。
Examples of SN2 Reactions of Benzyl Halides

Problem 35, 36, 38, 39
the Heck Reaction

The Heck Reaction
• Palladium-catalyzed coupling of an aryl or vinyl halide

with an alkene
芳基或⼄烯基⿄化物與烯烴的鈀催化偶聯
• Produces C–C bond at the less substituted end of the
alkene
在烯烴的較少取代的末端產⽣C-C鍵
• Triethylamine or sodium acetate is added to neutralize the
HX produced.
加入三⼄胺或⼄酸鈉以中和產⽣的HX。
Problem 27, 28
The Suzuki Reaction
• This is also called the Suzuki coupling.

這也被稱為鈴⽊耦合
• Palladium-catalyzed substitution that couples an aryl or
vinyl halide with an alkyl, alkenyl, or aryl boronic acid or
boronate ester
將芳基或⿄代⼄烯與烷基，烯基或芳基硼酸或硼酸酯
偶合的鈀催化的取代
Synthesis of Boronate Esters
• The boronate esters can be synthesized from alkyl-, vinyl-,

and arylboronic acids.
硼酸酯可以由烷基 - ，⼄烯基 - 和芳基硼酸合成。
• They can also be made by the hydroboration of double and
triple bonds.
它們也可以通過雙鍵和三鍵的合成來製造。
Examples of the Suzuki Reaction
© 2017 Pearson Education, Ltd. Problem 29, 30, 55, 62, 72

Problem 55

Problem 62

© 2017 Pearson Education, Ltd. Problem 50, 54
Problem 52, 53, 63, 67, 68
Problem 67

Problem 57, 76


Chapter 17 ArReaction

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Chapter 17 ArReaction

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Chapter 17 Reactions of Aromatic

• Although benzene’s pi electrons are in a stable aromatic system, they

© 2017 Pearson Education, Ltd.

Step 2: Loss of a proton gives the substitution product.

© 2017 Pearson Education, Ltd.

© 2017 Pearson Education, Ltd.

Step 2: Loss of a proton to give the products

© 2017 Pearson Education, Ltd.

• Chlorination is similar to bromination. AlCl3 is most often

© 2017 Pearson Education, Ltd.

• Iodination requires an acidic oxidizing agent, like nitric

© 2017 Pearson Education, Ltd.

• Before the electrophilic aromatic substitution can take place,

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• Sulfuric acid acts as a catalyst, allowing the reaction to be

© 2017 Pearson Education, Ltd.

• Formation of the nitronium ion is the preliminary step

© 2017 Pearson Education, Ltd.

Step 2: Loss of a proton gives nitrobenzene.

© 2017 Pearson Education, Ltd.

• Treatment with zinc, tin, or iron in dilute acid will reduce

© 2017 Pearson Education, Ltd.

• Sulfur trioxide (SO3) is the electrophile in the reaction.

© 2017 Pearson Education, Ltd.

• Benzene attacks sulfur trioxide, forming a sigma complex.

© 2017 Pearson Education, Ltd.

• In the desulfonation reaction, a proton adds to the ring (the

© 2017 Pearson Education, Ltd.

• The reaction is proven by using a deuterium ion (D+) rather than

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• Toluene reacts 25 times faster than benzene.

© 2017 Pearson Education, Ltd.

• Ortho and para attacks are preferred because their resonance

• When substitution occurs at the meta position, the positive charge is

© 2017 Pearson Education, Ltd.

• Alkyl groups are activating substituents and ortho,

• Anisole undergoes nitration about 10,000 times faster than benzene

Resonance stabilization is provided by a pi bond between the

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• Resonance forms show that the methoxy group cannot

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• A methoxy group is so strongly activating that anisole is

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• Aniline reacts with bromine water (without a catalyst) to

© 2017 Pearson Education, Ltd.

© 2017 Pearson Education, Ltd.

• Electrophilic substitution reactions for nitrobenzene are 100,000

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• The nitro group is a strongly deactivating group when considering its

© 2017 Pearson Education, Ltd.

• Meta substitution will not put the positive charge on the

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• Para substitution will place the positive charge on the

© 2017 Pearson Education, Ltd.

• In ortho and para substitution of acetophenone, one of the carbon

• The meta attack on acetophenone avoids bearing the

© 2017 Pearson Education, Ltd.

© 2017 Pearson Education, Ltd.

• Halogens are deactivators since they react slower than

• Resonance effect: The lone pairs on the halogen can be

© 2017 Pearson Education, Ltd.

• Inductive effect: Halogens are deactivating because they

© 2017 Pearson Education, Ltd.