Theoretically because there are 3 double bonds one might expect the amount of energy to be 3 times as much.

Size: px
Start display at page:

Download "Theoretically because there are 3 double bonds one might expect the amount of energy to be 3 times as much."

Transcription

1 18. Arenes There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six carbon ams with delocalised bonding. All of the organic substances we have looked at so far have been aliphatic Benzene belongs the aromatic class. Benzene s Structure The simplest arene is benzene. It has the molecular formula 6 6 Its basic structure is six ams in a hexagonal ring, with one am bonded each am Each am is bonded two other ams and one am by single covalent σbonds. This leaves one unused electron on each am in a p orbital, perpendicular the plane of the ring. The Six p electrons are delocalised in a ring structure above and below the plane of carbon ams In 1865 Kekule suggested the following structure for Benzene consisting of alternate single and double covalent bonds between the carbon ams This structure is not correct. Evidence suggests that all the bonds are the same length. In formulae we draw a circle show this delocalised system Abbreviated formula Displayed formula The six electrons in the pi bonds are delocalised and spread out over the whole ring. Delocalised means not attached a particular am. Benzene is a planar molecule.the evidence suggests all the bonds are the same and have a length and bond energy between a single and = double bond The bond angle is 120 o in Benzene Enthalpies of ydrogenation cyclohexene Non delocalised structure delocalised structure 3 2 cyclohexane = 120 kj/mol x3 = 360 kj/mol = 208kJ/mol Theoretically because there are 3 double bonds one might expect the amount of energy be 3 times as much. owever, the real amount of energy is less. The 6 pi electrons are delocalised and not arranged in 3 double bonds enthalpy This when represented on an energy level diagram shows that the delocalised benzene is more thermodynamically stable. 360 kj/mol Theoretical value = 152kJ/mol delocalisation energy = 208kJ/mol actual value The increase in stability connected delocalisation is called the delocalisation energy Reactions of Benzene Benzene does not generally undergo addition reactions because these would involve breaking up the delocalised system. Most of Benzene s reactions involve substituting one for another am or group of ams. Benzene has a high electron density and so attracts electrophiles. It reactions are usually electrophilic substitutions 1

2 Naming aromatic molecules Naming aromatic compounds can be complicated. The simplest molecules are derivatives of benzene and have benzene at the root of the name l N 2 2 Methylbenzene ethylbenzene chlorobenzene bromobenzene nitrobenzene benzenecarboxylic acid benzaldehyde If two or more substituents are present on the benzene ring, their positions must be indicated by the use of numbers. This should be done give the lowest possible numbers the substituents. When two or more different substituents are present, they are listed in alphabetical order and di, tri prefixes should be used N 3 N 2 3 1,3dimethylbenzene l N 2 1chloro 4methylbenzene 4hydroxybenzenecarboxylic acid 2,4,6trinitromethylbenzene In other molecules the benzene ring can be regarded as a substituent side group on another molecule, like alkyl groups are. The 6 5 group is known as the phenyl group. N phenylamine phenylethene 2phenylbutane phenylethanone phenylethanoate Toxicity of Benzene Benzene is a carcinogen (cancers causing molecule) and is banned for use in schools. Methylbenzene is less xic and also reacts more readily than benzene as the methyl side group releases electrons in the delocalised system making it more attractive electrophiles 2

3 Reactions of Benzene ombustion Benzene oxygen carbon dioxide water 6 6 (l) alogenation of Benzene hange in functional group: benzene omobenzene Reagents: omine onditions: iron(iii) bromide catalyst Fe 3 : Electrophillic Substitution verall Equation for reaction 2 Benzene will combust with a very sooty flame. The lower the carbon hydrogen ratio the sootier the flame. This reaction can be done with chlorine. The catalyst can be All 3 or Fel 3 It is possible create the iron(iii) bromide in situ by reacting iron with bromine Equation for Formation of electrophiles: (Learn!) All 3 l 2 All 4 l Fe 3 2 Fe 4 l l l Nitration of Benzene The ion reacts with the All 4 reform All 3 catalyst and l. hange in functional group: benzene nitrobenzene Reagents: conc nitric acid in the presence of concentrated sulphuric acid (catalyst) : Electrophilic Substitution Electrophile: N 2 verall Equation for reaction N 2 N 2 Equation for Formation of electrophile: (Learn!) N S 4 N 2 2S 4 3 All 4 All 3 l Importance of this reaction Nitration of benzene and other arenes is an important step in synthesising useful compounds e.g. explosive manufacture (like TNT, trinitroluene/ 2,4,6 trinitromethylbenzene) and formation of amines from which dyestuffs are manufactured. (The reaction for this is covered in the amines section.) N 2 N S 2 4 N 2 This reaction is done at 60 o. n using higher temperatures a second nitro group can be substituted on different positions on the ring The ion rejoins with the S 4 reform 2 S 4 catalyst. The horseshoe shape of the intermediate must not extend beyond s 2 6 S 4 2 S 4 If the benzene ring already has a side group e.g. methyl then the Nitro group can also join on different positions. Alevel does not require knowledge of what positions the groups go on. 3

4 ydrogenation of Benzene Reaction: benzene cyclohexane Reagents: ydrogen ondins: Nickel catalyst at 200 and 30 atm Type of reaction: Addition and reduction 3 2 Ni atalyst Sulphonation of Benzene hange of functional group: benzene sulphonated benzene Reagents: Fuming concentrated Sulphuric acid onditions: heat under reflux for several hours : Electrophillic Substitution Electrophile : S 3 (fuming sulphuric acid is S 3 dissolved in concentrated sulphuric acid) The sulfur trioxide can act as an electrophile because it can accept a pair of electrons The three oxygen ams on the sulfur give it a large δ charge S 3 S 3 sulphur trioxide Sulphonated arenes are used in drugs, detergents and dyestuffs Benzenesulphonic acid Friedel rafts Alkylation hange in functional group: benzene alkylbenzene Reagents: chloroalkane in the presence of anhydrous aluminium chloride catalyst onditions: heat under reflux : Electrophilic Substitution Any chloroalkane can be used Rl where R is any alkyl group Eg 3, 2 5. The electrophile is the R. Formation of the electrophile. All l 3 2 All 4 verall Equation for reaction 3 2 All 4 ethylbenzene 2 3 All 3 l The ion reacts with the All 4 reform All 3 catalyst and l. All 4 All 3 l 4

5 Friedel rafts Acylation hange in functional group: benzene phenyl kene Reagents: acyl chloride in the presence of anhydrous aluminium chloride catalyst onditions: heat under reflux (50 ) : Electrophilic Substitution Any acyl chloride can be used Rl where R is any alkyl group e.g. 3, 2 5. The electrophile is the R. Equation for Formation of the electrophile. All 3 3 l 3 All 4 verall Equation for reaction 3 All 4 3 phenylethanone All 3 l These are important reactions in organic synthesis because they introduce a reactive functional group on the benzene ring The ion reacts with the All 4 reform All 3 catalyst and l. All 4 All 3 l Effect of side groups on benzene ring Electron releasing side groups such as alkyl groups, phenols and amines releases electrons in the delocalised system making a higher electron density in the ring and it more attractive electrophiles. They will therefore carry out the substitution reactions more readily with milder conditions Effect of delocalisation on side groups with lone pairs If a group, a l am or an N 2 group is directly attached a benzene ring the delocalisation in the benzene ring will extend include the lone pairs on the N, and l. This changes the properties and reactions of the side group l N 2 chlorobenzene The l bond is made stronger. Typical halogenoalkane substitution and elimination reactions do not occur. Also the electron rich benzene ring will repel nucleophiles phenol Delocalisation makes the bond stronger and the bond weaker. Phenol does not act like an alcohol it is more acidic and does not oxidise phenylamine Less basic than aliphatic amines as lone pair is delocalised and less available for accepting a pron 5

6 Phenols In a phenol the group is directly attached the benzene ring. 2 In a phenol the lone pair of electrons on the oxygen is delocalised with the electron charge cloud of the arene ring. The delocalised bonding changes the reactivity of the group and the arene ring. Phenols are very weakly acidic. They are weaker acids than carboxylic acids. Both phenols and carboxylic acids will react with sodium metal and sodium hydroxide. nly carboxylic acids will react with sodium carbonate as a phenol is not strong enough an acid react. This is not a phenol, but is an alcohol because the group is attached an alkyl group rather than the benzene ring. Na Na ½ 2 Na Na 2 sodium phenoxide The sodium phenoxide compound is more soluble than the original phenol. So the solid phenol dissolves on addition of Na Reaction of phenol with omine Reagents: omine water onditions: room temp Phenol does not need a Fe 3 catalyst like benzene and undergoes multiple substitution whereas benzene will only add one. 2,4,6 tribromophenol The product in this reaction is a white solid In phenol the lone pair of electrons on the oxygen (p orbital) is partially delocalised in the ring. The electron density increases and the 2 is more polarised Phenols are used in the production of plastics, antiseptics, disinfectants and resins for paints. 6

6.1.1 Aromatic Compounds

6.1.1 Aromatic Compounds 6.1.1 Aromatic ompounds There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six carbon ams with delocalised

More information

3.10 Benzene : Aromatic Hydrocarbons / Arenes

3.10 Benzene : Aromatic Hydrocarbons / Arenes 3.10 Benzene : Aromatic ydrocarbons / Arenes There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six

More information

Aromatic Hydrocarbons / Arenes

Aromatic Hydrocarbons / Arenes Aromatic ydrocarbons / Arenes There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six carbon atoms

More information

Aromatic Hydrocarbons / Arenes

Aromatic Hydrocarbons / Arenes Aromatic ydrocarbons / Arenes There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six carbon atoms

More information

Plymstock School. Arenes. P.J.McCormack

Plymstock School. Arenes. P.J.McCormack Plymstock School 1 A2 Chemistry F324: Rings, Polymers & Analysis 4.1.1 - Arenes Arenes P.J.McCormack 2 4.1.1 Arenes Objective Checklist Draw the structure of benzene Explain the terms arene and aromatic

More information

Arenes occur naturally in many substances, and are present in coal and crude oil. Aspirin, for example, is an aromatic compound, an arene: HO

Arenes occur naturally in many substances, and are present in coal and crude oil. Aspirin, for example, is an aromatic compound, an arene: HO Naming Aromatic compounds contain one or more benzene rings (while aliphatic compounds do not contain benzene rings). Another term for a compound containing a benzene ring is arene. The basic benzene ring,

More information

17 Alcohols H H C C. N Goalby chemrevise.org 1 H H. Bond angles in Alcohols. Boiling points. Different types of alcohols H 2 C CH 2 CH 2

17 Alcohols H H C C. N Goalby chemrevise.org 1 H H. Bond angles in Alcohols. Boiling points. Different types of alcohols H 2 C CH 2 CH 2 17 Alcohols General formula alcohols n 2n+1 Naming Alcohols These have the ending -ol and if necessary the position number for the group is added between the name stem and the ol If the compound has an

More information

Q.1 Draw out suitable structures which fit the molecular formula C 6 H 6

Q.1 Draw out suitable structures which fit the molecular formula C 6 H 6 Aromatic compounds 2814 1 BENZENE Structure Primary analysis revealed benzene had an... empirical formula of and a molecular formula of 6 6 Q.1 Draw out suitable structures which fit the molecular formula

More information

Deduce the following information from the structure of estradiol, a phenol contain compound.

Deduce the following information from the structure of estradiol, a phenol contain compound. A2 Chemistry: F324 Rings, Polymers and Analysis The Chemistry of Phenol Learning Outcomes: All (E) State the uses of phenols Most (C) Describe the reactions of phenol with aqueous alkalis and with sodium

More information

H H O C C O H Carboxylic Acids and Derivatives C CH 2 C. N Goalby chemrevise.org. Strength of carboxylic acids.

H H O C C O H Carboxylic Acids and Derivatives C CH 2 C. N Goalby chemrevise.org. Strength of carboxylic acids. 19 arboxylic Acids and Derivatives Naming arboxylic acids These have the ending -oic acid but no number is necessary for the acid group as it must always be at the end of the chain. The numbering always

More information

18.1 Arenes benzene compounds Answers to Exam practice questions

18.1 Arenes benzene compounds Answers to Exam practice questions Pages 230 232 1 a) Benzene has a planar molecule ; with six carbon atoms in a regular hexagon. Each carbon atom forms a normal covalent ( ) bond with its two adjacent carbons atoms and a hydrogen atom.

More information

AROMATIC CHEMISTRY BENZENE

AROMATIC CHEMISTRY BENZENE AROMATIC CHEMISTRY BENZENE Definition of AROMATIC/ALIPHATIC?? The structure of benzene Percentage composition by mass gave the empirical formula as C 6 H 6, which led Kekulé to suggest the Structure shown.

More information

Option G: Further organic chemistry (15/22 hours)

Option G: Further organic chemistry (15/22 hours) Option G: Further organic chemistry (15/) TOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See 16... Core material: G1 G8 are core material

More information

Chapter 17 Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution

Chapter 17 Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Electrophile substitutes for a hydrogen on the benzene ring. Chapter 17: Aromatics 2-Reactions Slide 17-2 1 Mechanism Step

More information

Chapter 5. Aromatic Compounds

Chapter 5. Aromatic Compounds Chapter 5. Aromatic Compounds 5.1 Structure of Benzene: The Kekule Proposal Mid-1800s, benzene was known to have the molecular formula C 6 6. Benzene reacts with 2 in the presence of iron to give substitution

More information

7 Benzene and aromatic compounds Answers

7 Benzene and aromatic compounds Answers Practice: pages 161 163 1 Answer is D. Methyl takes precedence over nitro and, therefore, automatically takes position 1, which doesn t have to be included in the name. [1] 2 Answer is C. If Kekulé was

More information

6.10 Amines. Naming. N Goalby chemrevise.org 1 CH2 CH2

6.10 Amines. Naming. N Goalby chemrevise.org 1 CH2 CH2 6.10 Amines aming Amines These end in amine. There is, however, rather confusingly two ways of using this suffix. The exam board tend to use the common version where the name stem ends in -yl propylamine.

More information

Chem!stry. The Chemistry of Benzene C 6H 6 Macroconcept Models

Chem!stry. The Chemistry of Benzene C 6H 6 Macroconcept Models Chem!stry Name: ( ) Class: Date: / / The Chemistry of Benzene C 6H 6 Macroconcept Models This booklet covers essential information concerning the chemistry of benzene, including its structure, bonding

More information

Chapter 17. Reactions of Aromatic Compounds

Chapter 17. Reactions of Aromatic Compounds Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Although benzene s pi electrons are in a stable aromatic system, they are available to attack a strong electrophile to give

More information

TOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See

TOK: The relationship between a reaction mechanism and the experimental evidence to support it could be discussed. See Option G: Further organic chemistry (15/22 hours) SL students study the core of these options and HL students study the whole option (the core and the extension material). TOK: The relationship between

More information

ZAHID IQBAL WARRAICH

ZAHID IQBAL WARRAICH Q1 (a) State the reagents and conditions needed to convert benzene into (i) chlorobenzene, (ii) bromobenzene, (iii) nitrobenzene....[4] (b) The nitration of benzene is a two-step reaction that can be represented

More information

Chapter 15. Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution on Arenes. The first step is the slow, rate-determining step

Chapter 15. Reactions of Aromatic Compounds. Electrophilic Aromatic Substitution on Arenes. The first step is the slow, rate-determining step Electrophilic Aromatic Substitution on Arenes Chapter 15 Reactions of Aromatic Compounds The characteristic reaction of aromatic rings is substitution initiated by an electrophile halogenation nitration

More information

Benzenes & Aromatic Compounds

Benzenes & Aromatic Compounds Benzenes & Aromatic Compounds 1 Structure of Benzene H H C C C H C 6 H 6 H C C C H H A cyclic conjugate molecule Benzene is a colourless odourless liquid, boiling at 80 o C and melting at 5 o C. It is

More information

12/27/2010. Chapter 15 Reactions of Aromatic Compounds

12/27/2010. Chapter 15 Reactions of Aromatic Compounds Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen atom

More information

Chapter 17 Reactions of Aromatic Compounds

Chapter 17 Reactions of Aromatic Compounds rganic Chemistry, 6 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds Jo Blackburn Richland College, Dallas, TX Dallas County Community College District 2006, Prentice all Electrophilic

More information

Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Reactivity of Benzene

Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Reactivity of Benzene hapter 16 hemistry of Benzene: Electrophilic Aromatic Substitution Reactivity of Benzene - stabilization due to aromaticity makes benzene significantly less reactive than isolated alkenes 2 no reaction

More information

18: Organic Chemistry III 18A. Arenes

18: Organic Chemistry III 18A. Arenes 18: rganic hemistry III 18A. Arenes There are two major classes of organic chemicals aliphatic : straight or branched chain organic substances aromatic or arene: includes one or more ring of six carbon

More information

Organic Mechanisms 1

Organic Mechanisms 1 Organic Mechanisms 1 Concepts The key ideas required to understand this section are: Concept Book page Chemical properties of alkanes 314 Chemical properties of alkenes 318 Bonding in alkenes 320 Bonding

More information

F324: Rings, Polymers and Analysis Arenes

F324: Rings, Polymers and Analysis Arenes F324: Rings, Polymers and Analysis 4.1.1. Arenes 1. A chemist was investigating the reactions of benzene, phenol and cyclohexene with bromine. She found that they all reacted with bromine but under different

More information

Aromatic Compounds II

Aromatic Compounds II 2302272 Org Chem II Part I Lecture 2 Aromatic Compounds II Instructor: Dr. Tanatorn Khotavivattana E-mail: tanatorn.k@chula.ac.th Recommended Textbook: Chapter 17 in Organic Chemistry, 8 th Edition, L.

More information

BENZENE AND AROMATIC COMPOUNDS

BENZENE AND AROMATIC COMPOUNDS BENZENE AND AROMATIC COMPOUNDS The discovery of benzene: 1825 - Michael Faraday, empirical formula of C 1834 - Eilhard Mitscherlich synthesized benzin from gum benzoin, empirical formula C Aromatic The

More information

Chapter 13 Reactions of Arenes Electrophilic Aromatic Substitution

Chapter 13 Reactions of Arenes Electrophilic Aromatic Substitution . 13 hapter 13 eactions of Arenes lectrophilic Aromatic ubstitution lectrophiles add to aromatic rings in a fashion somewhat similar to the addition of electrophiles to alkenes. ecall: 3 4 Y 1 4 2 1 δ

More information

The mechanism of the nitration of methylbenzene is an electrophilic substitution.

The mechanism of the nitration of methylbenzene is an electrophilic substitution. Q1.Many aromatic nitro compounds are used as explosives. One of the most famous is 2-methyl-1,3,5-trinitrobenzene, originally called trinitrotoluene or TNT. This compound, shown below, can be prepared

More information

BRCC CHM 102 Class Notes Chapter 13 Page 1 of 6

BRCC CHM 102 Class Notes Chapter 13 Page 1 of 6 BRCC CHM 102 ass Notes Chapter 13 Page 1 of 6 Chapter 13 Benzene and Its Derivatives aliphatic hydrocarbons include alkanes, alkenes, and alkynes aromatic hydrocarbons compounds that contain one or more

More information

Carboxylic acid derivatives

Carboxylic acid derivatives arboxylic acid derivatives Acyl hlorides and Acid Anhydrides N Goalby hemrevise.org arboxylic acid derivatives carboxylic acid (ethanoic acid) 3 l Acyl hloride (ethanoyl chloride) key 3 3 Acid Anhydride

More information

Chapter 4: Aromatic Compounds. Bitter almonds are the source of the aromatic compound benzaldehyde

Chapter 4: Aromatic Compounds. Bitter almonds are the source of the aromatic compound benzaldehyde Chapter 4: Aromatic Compounds Bitter almonds are the source of the aromatic compound benzaldehyde Sources of Benzene Benzene, C 6 H 6, is the parent hydrocarbon of the especially stable compounds known

More information

Organic Chemistry SL IB CHEMISTRY SL

Organic Chemistry SL IB CHEMISTRY SL Organic Chemistry SL IB CHEMISTRY SL 10.1 Fundamentals of organic chemistry Understandings: A homologous series is a series of compounds of the same family, with the same general formula, which differ

More information

Organic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall

Organic Chemistry, 7 L. G. Wade, Jr. Chapter , Prentice Hall Organic Chemistry, 7 th Edition L. G. Wade, Jr. Chapter 17 Reactions of Aromatic Compounds 2010, Prentice Hall Electrophilic Aromatic Substitution Although h benzene s pi electrons are in a stable aromatic

More information

A LEVEL CHEMISTRY TOPIC 18 AROMATIC CHEMISTRY TEST

A LEVEL CHEMISTRY TOPIC 18 AROMATIC CHEMISTRY TEST A LEVEL CHEMISTRY TOPIC 18 AROMATIC CHEMISTRY TEST Answer all questions Max 50 marks Name.. Mark../50...% Grade 1. Page 1 2. The hydrocarbons benzene and cyclohexene are both unsaturated compounds. Benzene

More information

Some..(A) Describe the synthesis of azo dyes and the full chemical equations for each step.

Some..(A) Describe the synthesis of azo dyes and the full chemical equations for each step. A2 Chemistry: F324 Rings, Polymers and Analysis Amines Learning Outcomes: All.. (E) Most.. (C) Explain why amines are basic Draw the structure of a primary secondary and tertiary amine Describe the reactions

More information

Alkyl phenyl ketones are usually named by adding the acyl group as prefix to phenone.

Alkyl phenyl ketones are usually named by adding the acyl group as prefix to phenone. Aldehydes, Ketones and Carboxylic Acids Nomenclature of aldehydes and ketones Aldehydes: Often called by their common names instead of IUPAC names. Ketones: Derived by naming two alkyl or aryl groups bonded

More information

Vision. Cis-trans isomerism is key to vision. How rods work H 3 C CH 3. Protein opsin. 11-cis-retinal. Opsin. Rhodopsin.

Vision. Cis-trans isomerism is key to vision. How rods work H 3 C CH 3. Protein opsin. 11-cis-retinal. Opsin. Rhodopsin. Vision Cis-trans isomerism is key to vision. 3 C 11 12 3 C C 3 3 C O C 3 11-cis-retinal Protein opsin 3 C 11 12 3 C C 3 3 C N Opsin C 3 Rhodopsin Light photons 3 C N Opsin 3 C 11 12 3 C C 3 C 3 ow rods

More information

4. AROMATIC COMPOUNDS

4. AROMATIC COMPOUNDS BOOKS 1) Organic Chemistry Structure and Function, K. Peter C. Vollhardt, Neil Schore, 6th Edition 2) Organic Chemistry, T. W. Graham Solomons, Craig B. Fryhle 3) Organic Chemistry: A Short Course, H.

More information

Acceptable sequence of stages are: chlorination. nitration, reduction, chlorination nitration. nitration, chlorination, reduction, reduction

Acceptable sequence of stages are: chlorination. nitration, reduction, chlorination nitration. nitration, chlorination, reduction, reduction Question er Mark Guidance 1 (a) (i) Response requires three stages Acceptable sequence of stages are: chlorination nitration, reduction, chlorination nitration nitration, chlorination, reduction, reduction

More information

Electrophilic Aromatic Substitution. Dr. Mishu Singh Department of chemistry Maharana Pratap Govt.P.G.College Hardoi

Electrophilic Aromatic Substitution. Dr. Mishu Singh Department of chemistry Maharana Pratap Govt.P.G.College Hardoi Electrophilic Aromatic Substitution Dr. Mishu Singh Department of chemistry Maharana Pratap Govt.P.G.College Hardoi 1 Recall the electophilic addition of HBr (or Br2) to alkenes H + nu cleophile H Br H

More information

ammonia primary amine secondary amine tertiary amine quaternary ammonium salt (NOT amines) H CH 3 CH 3 CH 2

ammonia primary amine secondary amine tertiary amine quaternary ammonium salt (NOT amines) H CH 3 CH 3 CH 2 AMIES 1) TYPES F AMIES Amines can be classed as primary, secondary and tertiary. Amines are related to ammonia ( 3 ). Aromatic amines have the joined directly to the benzene ring. Quaternary ammonium salts

More information

ALKENES. select the longest chain of C atoms containing the double bond; end in ENE

ALKENES. select the longest chain of C atoms containing the double bond; end in ENE Alkenes 1 ALKENES Structure form a homologous series of general formula n 2n - non cyclic alkenes only contain a carbon-carbon double bond somewhere in their structure unsaturated hydrocarbons - can still

More information

Chapter 15 Reactions of Aromatic Compounds

Chapter 15 Reactions of Aromatic Compounds Chapter 15 1 Chapter 15 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution Arene (Ar-H) is the generic term for an aromatic hydrocarbon The aryl group (Ar) is derived by removal of a hydrogen

More information

OCR (A) Chemistry A-level. Module 6: Organic Chemistry and Analysis

OCR (A) Chemistry A-level. Module 6: Organic Chemistry and Analysis OCR (A) Chemistry A-level Module 6: Organic Chemistry and Analysis Organic Synthesis Notes by Adam Robertson DEFINITIONS Heterolytic fission: The breaking of a covalent bond when one of the bonded atoms

More information

Chapter 19: Benzene and Aromatic Substitution Reactions [Sections: 18.2, 18.6; ]

Chapter 19: Benzene and Aromatic Substitution Reactions [Sections: 18.2, 18.6; ] Chapter 19: Benzene and Aromatic Substitution eactions [Sections: 18.2, 18.6; 19.1-19.12] omenclature of Substituted Benzenes i. Monosubstituted Benzenes C 2 C 3 ii. Disubstituted Benzenes X X X Y Y Y

More information

N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. Reverse process of dehydration of an alcohol

N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. Reverse process of dehydration of an alcohol An Introduction to Organic hemistry N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. ydration (Addition) Reverse process of dehydration of an alcohol

More information

4.1.3 Alkenes. N Goalby chemrevise.org. Formation of π bond p orbitals C C C C. Alkenes contain a carboncarbon. General formula is CnH2n

4.1.3 Alkenes. N Goalby chemrevise.org. Formation of π bond p orbitals C C C C. Alkenes contain a carboncarbon. General formula is CnH2n 4.1.3 Alkenes Alkenes are unsaturated hydrocarbons General formula is n2n Alkenes contain a carboncarbon double bond somewhere in their structure Ethene Propene Numbers need to be added to the name when

More information

11/26/ Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds

11/26/ Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds. Polycyclic Aromatic Compounds 9.5 Polycyclic Aromatic Compounds The general concept of aromaticity can be extended to include polycyclic aromatic compounds Benzo[a]pyrene is one of the cancer-causing substances found in tobacco smoke

More information

William H. Brown & Christopher S. Foote

William H. Brown & Christopher S. Foote William. Brown & Christopher S. Foote Requests for permission to make copies of any part of the work should be mailed to:permissions Department, arcourt Brace & Company, 6277 Sea arbor Drive, Orlando,

More information

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution Chem 263 ct. 8, 2013 lectrophilic Aromatic Substitution Benzene appears to be a remarkably stable and unreactive compared to alkenes, such as cyclohexene or ethylene, or even alkanes, such as cyclohexane

More information

240 Chem. Aromatic Compounds. Chapter 6

240 Chem. Aromatic Compounds. Chapter 6 240 Chem Aromatic Compounds Chapter 6 1 The expressing aromatic compounds came to mean benzene and derivatives of benzene. Structure of Benzene: Resonance Description C 6 H 6 1.It contains a six-membered

More information

Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution Chem 263 Sept 29, 2016 lectrophilic Aromatic Substitution Benzene appears to be a remarkably stable (36 kcal/mole more) and unreactive compared to alkenes, such as cyclohexene or ethylene, or even alkanes,

More information

General formula is CnH2n. Propene. But-1-ene. C-C pi bond. Formation of π bond in alkenes p orbitals Rotation can occur around a sigma bond

General formula is CnH2n. Propene. But-1-ene. C-C pi bond. Formation of π bond in alkenes p orbitals Rotation can occur around a sigma bond 4.1.3 Alkenes Alkenes are unsaturated hydrocarbons General formula is n2n Alkenes contain a carboncarbon double bond somewhere in their structure Ethene Propene Numbers need to be added to the name when

More information

11/30/ Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions

11/30/ Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions Chapter 9 Problems: 9.1-29, 32-34, 36-37, 39-45, 48-56, 58-59, 61-69, 71-72. 9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic

More information

16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 7 th edition

16. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 7 th edition 16. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 7 th edition Substitution Reactions of Benzene and Its Derivatives Benzene is aromatic: a cyclic conjugated

More information

Module 4 revision guide: Compounds with C=O group

Module 4 revision guide: Compounds with C=O group opyright N Goalby Bancroft's School Module 4 revision guide: ompounds with = group arbonyls: Aldehydes and Ketones arbonyls are compounds with a = bond, they can be either aldehydes or ketones. 3 ethanal

More information

The now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine.

The now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine. The now-banned diet drug fen-phen is a mixture of two synthetic substituted benzene: fenfluramine and phentermine. Chemists have synthesized compounds with structures similar to adrenaline, producing amphetamine.

More information

CHAPTER 16 - CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION

CHAPTER 16 - CHEMISTRY OF BENZENE: ELECTROPHILIC AROMATIC SUBSTITUTION CAPTR 16 - CMISTRY F BNZN: LCTRPILIC ARMATIC SUBSTITUTIN As stated in the previous chapter, benzene and other aromatic rings do not undergo electrophilic addition reactions of the simple alkenes but rather

More information

1.3 Reactions of Hydrocarbons

1.3 Reactions of Hydrocarbons 1.3 Reactions of ydrocarbons All hydrocarbons readily burn in air to give carbon dioxide and water, with the release of large amounts of energy (Figure 1); this chemical reaction accounts for the extensive

More information

I5 ELECTROPHILIC SUBSTITUTIONS OF

I5 ELECTROPHILIC SUBSTITUTIONS OF Section I Aromatic chemistry I5 ELECTPILIC SUBSTITUTINS F MN-SUBSTITUTED AMATIC INGS Key Notes ortho, meta and para substitution Substituent effect eaction profile Activating groups inductive o/p Deactivating

More information

Name/CG: 2012 Term 2 Organic Chemistry Revision (Session II) Deductive Question

Name/CG: 2012 Term 2 Organic Chemistry Revision (Session II) Deductive Question Name/G: 2012 Term 2 rganic hemistry Revision (Session II) Deductive Question 1(a) A yellow liquid A, 7 7 N 2, reacts with alkaline potassium manganate (VII) and on acidification gives a yellow solid B,

More information

Organic Chemistry. Second Edition. Chapter 19 Aromatic Substitution Reactions. David Klein. Klein, Organic Chemistry 2e

Organic Chemistry. Second Edition. Chapter 19 Aromatic Substitution Reactions. David Klein. Klein, Organic Chemistry 2e Organic Chemistry Second Edition David Klein Chapter 19 Aromatic Substitution Reactions Copyright 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e 19.1 Introduction to Electrophilic

More information

Lecture Topics: I. Electrophilic Aromatic Substitution (EAS)

Lecture Topics: I. Electrophilic Aromatic Substitution (EAS) Reactions of Aromatic Compounds Reading: Wade chapter 17, sections 17-1- 17-15 Study Problems: 17-44, 17-46, 17-47, 17-48, 17-51, 17-52, 17-53, 17-59, 17-61 Key Concepts and Skills: Predict and propose

More information

Where circles have been placed round charges, this is for clarity only and does not indicate a requirement. ALLOW delocalised carboxylate.

Where circles have been placed round charges, this is for clarity only and does not indicate a requirement. ALLOW delocalised carboxylate. Question (a) Answer Mark Guidance Where circles have been placed round charges, this is for clarity only and does not indicate a requirement (i) ALLOW correct structural OR displayed OR skeletal formulae

More information

Organic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology

Organic Chemistry. M. R. Naimi-Jamal. Faculty of Chemistry Iran University of Science & Technology Organic Chemistry M. R. Naimi-Jamal Faculty of Chemistry Iran University of Science & Technology Chapter 5-2. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry,

More information

UNIT 11 ALCOHOLS, PHENOLS & ETHERS

UNIT 11 ALCOHOLS, PHENOLS & ETHERS UNIT 11 ALCOHOLS, PHENOLS & ETHERS Alcohols and Phenol are Organic compound with a hydroxyl group (- OH) as functional group. Ethers are identified by a functional group ( 0 ). Cyclic alcohols are named

More information

Chapter 23 Phenols CH. 23. Nomenclature. The OH group takes precedence as the parent phenol.

Chapter 23 Phenols CH. 23. Nomenclature. The OH group takes precedence as the parent phenol. CH. 23 Chapter 23 Phenols Nomenclature The OH group takes precedence as the parent phenol. Carboxyl and acyl groups take precedence over the OH group. The OH group is a strong electron-donating group through

More information

Chapter 17 Reactions of Aromatic Compounds

Chapter 17 Reactions of Aromatic Compounds Chapter 17 Reactions of Aromatic Compounds Electrophilic Aromatic Substitution o General reaction - an electrophile replaces a hydrogen Electrons of pi system attack strong electrophile, generating resonancestabilized

More information

Benzene and Aromatic Compounds

Benzene and Aromatic Compounds 1 Background Benzene and Aromatic Compounds Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Benzene has four degrees of unsaturation, making it a highly unsaturated hydrocarbon. Whereas

More information

Reactions of Aromatic Compounds. Aromatic compounds do not react like other alkenes. With an appropriate catalyst, however, benzene will react

Reactions of Aromatic Compounds. Aromatic compounds do not react like other alkenes. With an appropriate catalyst, however, benzene will react Reactions of Aromatic Compounds Aromatic compounds do not react like other alkenes 2 Fe 3 2 Does not form A major part of the problem for this reaction is the product has lost all aromatic stabilization,

More information

Class XI Chapter 13 Hydrocarbons Chemistry

Class XI Chapter 13 Hydrocarbons Chemistry Question 13.1: How do you account for the formation of ethane during chlorination of methane? Chlorination of methane proceeds via a free radical chain mechanism. The whole reaction takes place in the

More information

dihalogenoalkane H 2, Nickel Catalyst KOH alcoholic HBr, HCl Br Cl Elimination KOH aqueous heat under reflux Nucleophilic substitution

dihalogenoalkane H 2, Nickel Catalyst KOH alcoholic HBr, HCl Br Cl Elimination KOH aqueous heat under reflux Nucleophilic substitution 7 AS mechanisms dihalogenoalkane poly(alkene) Br 2, 2 KO aqueous room temp Electrophilic addition heat under reflux Nucleophilic substitution high pressure atalyst polymerization alkene KMnO 4 oxidation

More information

Amines. Types of Amines. chemrevise.org. N Goalby Chemrevise.org. primary amine (one C attached to N) H. Secondary amine (two C s.

Amines. Types of Amines. chemrevise.org. N Goalby Chemrevise.org. primary amine (one C attached to N) H. Secondary amine (two C s. Amines Goalby hemrevise.org Types of Amines primary amine (one attached to ) Secondary amine (two s attached to ) 3 2 2 3 name : diethylamine It is also possible to have aromatic amines 2 phenylamine name:

More information

Chemistry of Benzene: Electrophilic Aromatic Substitution

Chemistry of Benzene: Electrophilic Aromatic Substitution Chemistry of Benzene: Electrophilic Aromatic Substitution Why this Chapter? Continuation of coverage of aromatic compounds in preceding chapter focus shift to understanding reactions Examine relationship

More information

Organic Chemistry Worksheets

Organic Chemistry Worksheets Highlight the single longest, continuous carbon-carbon chain. Note the alkyl branches that are connected to the root chain. Count the carbons in the root chain, starting from the end closest to the alkyl

More information

dihalogenoalkane H 2, KOH alcoholic heat under reflux Elimination PCl 5, PBr 3, PI 3 Heat under reflux substitution KOH aqueous heat under reflux

dihalogenoalkane H 2, KOH alcoholic heat under reflux Elimination PCl 5, PBr 3, PI 3 Heat under reflux substitution KOH aqueous heat under reflux 7. AS mechanisms dihalogenoalkane poly(alkene) 2, l 2 room temp Electrophilic addition KO aqueous heat under reflux Nucleophilic substitution high pressure atalyst polymerization alkene KMnO 4 oxidation

More information

Chapter 25: The Chemistry of Life: Organic and Biological Chemistry

Chapter 25: The Chemistry of Life: Organic and Biological Chemistry Chemistry: The Central Science Chapter 25: The Chemistry of Life: Organic and Biological Chemistry The study of carbon compounds constitutes a separate branch of chemistry known as organic chemistry The

More information

08. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 6 th edition, Chapter 16

08. Chemistry of Benzene: Electrophilic Aromatic Substitution. Based on McMurry s Organic Chemistry, 6 th edition, Chapter 16 08. Chemistry of Benzene: Electrophilic Aromatic Substitution Based on McMurry s Organic Chemistry, 6 th edition, Chapter 16 Benzene is a nucleophile p electrons make benzene nucleophile, like alkenes.

More information

Nitro compounds are named by writing the word nitro before the name of the parent compound.

Nitro compounds are named by writing the word nitro before the name of the parent compound. Nitro compounds are an important class of organic compounds which may be regarded as derived from hydrocarbons by the replacement of one or more hydrogen atoms by nitro (NO₂) groups. Nitro arenes(i.e.

More information

HALOGENOALKANES (HALOALKANES) Structure Contain the functional group C-X where X is a halogen (F,Cl,Br or I)

HALOGENOALKANES (HALOALKANES) Structure Contain the functional group C-X where X is a halogen (F,Cl,Br or I) aloalkanes 2812 1 ALOGENOALKANES (ALOALKANES) Structure ontain the functional group X where X is a halogen (F,l, or I) Types alogenoalkanes halogen is attached to an aliphatic skeleton alkyl group aloarenes

More information

Chapter 15. Reactions of Aromatic Compounds. 1. Electrophilic Aromatic Substitution Reactions

Chapter 15. Reactions of Aromatic Compounds. 1. Electrophilic Aromatic Substitution Reactions hapter 15 eactions of Aromatic ompounds 1. Electrophilic Aromatic Substitution eactions v verall reaction reated by Professor William Tam & Dr. Phillis hang opyright S 3 2 S 4 S 3 2. A General Mechanism

More information

Chemistry 204: Benzene and Aromaticity

Chemistry 204: Benzene and Aromaticity Chemistry 204: Benzene and Aromaticity Structure of and Bonding in Benzene benzene, C 6 H 6, was first isolated in 1825 (Michael Faraday), but it was not until more than 100 years later that an adequate

More information

More Nomenclature: Common Names for Selected Aromatic Groups. Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings.

More Nomenclature: Common Names for Selected Aromatic Groups. Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings. More Nomenclature: Common Names for Selected Aromatic Groups Phenyl group = or Ph = C 6 H 5 = Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings. Benzyl = Bn = It has a -CH

More information

Nitration of (Trifluoromethyl( Trifluoromethyl)benzene CF 3 HNO 3 + +

Nitration of (Trifluoromethyl( Trifluoromethyl)benzene CF 3 HNO 3 + + Effect on Rate Rate and Regioselectivity in Electrophilic Aromatic Substitution A substituent already present on the ring affects both the rate and regioselectivity of electrophilic aromatic substitution.

More information

Carbonyls. Aldehydes and Ketones N Goalby chemrevise.org. chemrevise.org

Carbonyls. Aldehydes and Ketones N Goalby chemrevise.org. chemrevise.org arbonyls Aldehydes and Ketones N Goalby chemrevise.org arbonyls are compounds with a = bond, they can be either aldehydes or ketones. 3 ethanal 3 3 propanone If the = is on the end of the chain with an

More information

DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE

DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 8 Dr Ali El-Agamey Nomenclature of Benzene Derivatives Nomenclature of Benzene Derivatives To name a benzene ring with one substituent, name

More information

B. (3 pts) The following values are independent of the operating frequency of the NMR: a. Coupling constant; c. Chemical shift; b. Gyromagnetic ratio;

B. (3 pts) The following values are independent of the operating frequency of the NMR: a. Coupling constant; c. Chemical shift; b. Gyromagnetic ratio; CEMISTRY 314-01 MIDTERM # 1 answer key September 29, 2009 Statistics: Average: 70 pts (70%); ighest: 96 pts (96%); Lowest: 37 pts (37%) Number of students performing at or above average: 16 (57%) Number

More information

H 2 SO 4 Ar-NO 2 + H2O

H 2 SO 4 Ar-NO 2 + H2O Phenyl group: Shorthand for phenyl: Ph, C 6 5,. An aryl group is an aromatic group: phenyl, substituted phenyl, or other aromatic group. Shorthand: Ar Generalized electrophilic aromatic substitution: E

More information

QUESTIONSHEET 1. ELECTROPHILIC SUBSTITUTION I (Nitration)

QUESTIONSHEET 1. ELECTROPHILIC SUBSTITUTION I (Nitration) TOPI4 ASWERS & MARK SEMES QUESTIOSEET 1 ELETROPILI SUBSTITUTIO I (itration) a) πelectrons in arenes are delocalised electrophiles are less strongly attracted b) (i) O2 O 3 2 O (ii) oncentrated sulfuric

More information

HALOALKANES. Structure Contain the functional group C-X where X is a halogen (F,Cl,Br or I)

HALOALKANES. Structure Contain the functional group C-X where X is a halogen (F,Cl,Br or I) aloalkanes AS3 1 ALOALKANES Structure ontain the functional group X where X is a halogen (F,l, or I) Types aloalkanes halogen is attached to an aliphatic skeleton alkyl group aloarenes halogen is attached

More information

Aromatic Compounds and Amines

Aromatic Compounds and Amines Aromatic Compounds and Amines 22 8 Consider compound P shown below that is formed by the reaction of benzene with an electrophile. O C CH 2 CH 3 P 8 (a) Give the two substances that react together to form

More information

Some Families of Organic Compounds HL

Some Families of Organic Compounds HL Name: Organic Chemistry 22. Some Families of Organic Compounds Objectives -define tetrahedral carbon -explain what is meant by the term alcohol -describe the alcohols as a homologous series of organic

More information

16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2

16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based

More information

16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2

16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 16. Chemistry of Benzene: Electrophilic Aromatic Substitution جانشینی الکتروندوستی آروماتیک شیمی آلی 2 Dr M. Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based

More information

REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2)

REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2) REASONING QUESTIONS FROM ORGANIC CHEMISTRY (CH. 1 & 2) 1.) Why do haloalkenes under go nucleophillic substitution whereas haloarenes under go electophillic substitution. Ans. Due to more electro negative

More information