Aromatic Compounds II
|
|
- Evangeline Austin
- 5 years ago
- Views:
Transcription
1 Org Chem II Part I Lecture 2 Aromatic Compounds II Instructor: Dr. Tanatorn Khotavivattana tanatorn.k@chula.ac.th Recommended Textbook: Chapter 17 in Organic Chemistry, 8 th Edition, L. G. Wade, Jr., 2010, Prentice Hall (Pearson Education)
2 Basic Knowledge in Organic Reactions 1 5 main types of reactions Addition Substitution Elimination Radical Oxidation Reduction Reactions
3 Basic Knowledge in Organic Reactions 2 Nucleophile / Electrophile / Base / Acid / Leaving group
4 Basic Knowledge in Organic Reactions 3 Arrow pushing
5 Basic Knowledge in Organic Reactions 4 Examples
6 Basic Knowledge in Organic Reactions 5 Examples
7 Reactions of Aromatic Compounds 6 Electrophilic Aromatic Substitution Halogenation (usually Br 2 ) Nitration Sulfonation Friedel-Craft Alkylation/Acylation Nucleophilic Aromatic Substitution Reduction of Aromatic Rings Birch reduction Will not cover Catalytic hydrogenation Will not cover Miscellaneous Reaction at the side chain Will not cover + Lecture 5-6 Oxidation of phenol Will not cover
8 Electrophilic Aromatic Substitution 7 Like an alkene, benzene has clouds of pi electrons above and below its sigma bond framework. Although benzene s pi electrons are in a stable aromatic system, they are available to attack a strong electrophile to give a carbocation. (nonaromatic) Loss of aromaticity = highly endothermic nature of this first step. Regains aromaticity by loss of the proton on the tetrahedral carbon atom overall reaction: substitution of an electrophile (E + ) for a proton (H + )
9 Electrophilic Aromatic Substitution 8 Mechanism
10 EAS #1: Halogenation of Benzene 9 Benzene is not as reactive as alkenes, which react rapidly with bromine at room temperature to give addition products
11 EAS #1: Halogenation of Benzene 10 Bromination Bromine itself is not sufficiently electrophilic to react with benzene. A strong Lewis acid such as FeBr 3 catalyzes the reaction by forming a stronger electrophile with a weakened Br Br bond and a partial positive charge on one of the bromine atoms Mechanism
12 EAS #1: Halogenation of Benzene 11 Bromination
13 EAS #1: Halogenation of Benzene 12 Formation of the sigma complex is rate-limiting, and the transition state leading to it occupies the highest-energy point on the energy diagram.
14 EAS #1: Halogenation of Benzene 13 Chlorination Iodination
15 EAS #2: Nitration of Benzene 14 Benzene reacts with a mixture of nitric acid and sulfuric acid to give nitrobenzene (sulfuric acid is a catalyst) Mechanism
16 EAS #2: Nitration of Benzene 15
17 (EAS #2: Nitration of Benzene) 16 Aromatic nitro groups are easily reduced to amino groups by treatment with reducing agents such as tin, zinc, or iron in dilute acid. Nitration followed by reduction is often the best method for adding an amino group to an aromatic ring.
18 EAS #3: Sulfonation of Benzene 17 Arylsulfonic acids are synthesized by sulfonation of benzene derivatives, using fuming sulfuric acid : sulfur trioxide SO 3 in H 2 SO 4
19 EAS #3: Sulfonation of Benzene Mechanism 18
20 EAS #3: Sulfonation of Benzene 19
21 (EAS #3: Sulfonation of Benzene) 20 Desulfonation Sulfonation is reversible, and a sulfonic acid group may be removed from an aromatic ring by heating in dilute sulfuric acid. Mechanism
22 Effects of substituents on EAS 21 Rate: Toluene reacts about 25 times faster than benzene (toluene is activated toward EAS and the methyl group is an activating group). Position: Nitration of toluene gives a mixture of products, primarily those resulting from substitution at the ortho and para positions (the methyl group is an ortho, para-director).
23 Effects of substituents on EAS 22 The rate-limiting step for EAS is the first step In ortho or para substitution of toluene, the positive charge is spread over two secondary carbons and one tertiary (3 ) carbon
24 Effects of substituents on EAS 23
25 Effects of substituents on EAS 24
26 Effects of substituents on EAS 25 1) Activating, Ortho, Para-Directing Substituents 1.1) Alkyl groups:
27 Effects of substituents on EAS 26 1) Activating, Ortho, Para-Directing Substituents 1.2) Alkoxy groups: Anisole undergoes nitration about 10,000 times faster than benzene and about 400 times faster than toluene.
28 Effects of substituents on EAS 27
29 Effects of substituents on EAS 28 1) Activating, Ortho, Para-Directing Substituents 1.2) Alkoxy groups: A methoxy group is so strongly activating that anisole quickly brominates in water without a catalyst. In the presence of excess bromine, this reaction proceeds to the tribromide.
30 Effects of substituents on EAS 29 1) Activating, Ortho, Para-Directing Substituents 1.3) Amine groups: Like an alkoxyl group, a nitrogen atom with a nonbonding pair of electrons serves as a powerful activating group. Aniline undergoes a fast bromination (without a catalyst) in bromine water to give the tribromide.
31 Effects of substituents on EAS 1.3) Amine groups: 30
32 Effects of substituents on EAS 31 2) Deactivating, Meta-Directing Substituents Nitrobenzene is about 100,000 times less reactive than benzene, giving the meta isomer as the major product Nitro group is a strong deactivating group. - The positively charged nitrogen inductively withdraws electron density
33 Effects of substituents on EAS 32
34 Effects of substituents on EAS 33
35 Effects of substituents on EAS 34 2) Deactivating, Meta-Directing Substituents Carbonyl groups Examples:
36 3) Halogen Substituents: Deactivating, but Ortho, Para-Directing the halogens are strongly electronegative, withdrawing electron density from a carbon atom through the sigma bond (inductive withdrawal) 2. the halogens have nonbonding electrons that can donate electron density through pi bonding (resonance donation).
37 Effects of substituents on EAS 36 3) Halogen Substituents: Deactivating, but Ortho, Para-Directing
38 Effects of substituents on EAS 37
39 Effects of substituents on EAS 38 Effects of Multiple Substituents Rate Position
40 Effects of substituents on EAS 39 Effects of Multiple Substituents
41 Effects of substituents on EAS 40 Effects of Multiple Substituents
42 Problem #1 41
43 EAS #4: Friedel Crafts alkylation 42 Carbocations are perhaps the most important electrophiles, because this substitution forms a new carbon carbon bond. In the presence of Lewis acid catalysts such as aluminum chloride or ferric chloride alkyl halides were found to alkylate benzene to give alkylbenzenes. Example
44 EAS #4: Friedel Crafts alkylation 43 Carbocations are perhaps the most important electrophiles, because this substitution forms a new carbon carbon bond. In the presence of Lewis acid catalysts such as aluminum chloride or ferric chloride alkyl halides were found to alkylate benzene to give alkylbenzenes. Example
45 Mechanism 44
46 EAS #4: Friedel Crafts alkylation 45 Alkenes can be used as a carbocation sources Alcohols can be used as a carbocation sources
47 EAS #4: Friedel Crafts alkylation 46 Limitation 1: - Susceptible to carbocation rearrangements
48 EAS #4: Friedel Crafts alkylation 47 Limitation 2: - alkyl groups are activating substituents, the product of the Friedel Crafts alkylation is more reactive than the starting material. Multiple alkylations are hard to avoid. - The problem of overalkylation can be minimized by using a large excess of benzene.
49 Problem #2 48
50 Problem #3 49
51 EAS #5: Friedel Crafts acylation 50 An acyl group is a carbonyl group with an alkyl group attached. Acyl groups are named systematically by dropping the final -e from the alkane name and adding the -oyl suffix. An acyl chloride is an acyl group bonded to a chlorine atom.
52 EAS #5: Friedel Crafts acylation 51 In the presence of aluminum chloride, an acyl chloride reacts with benzene (or an activated benzene derivative) to give a phenyl ketone
53 EAS #5: Friedel Crafts acylation 52 Mechanism
54 EAS #5: Friedel Crafts acylation 53 Para substitution usually prevails (when the aromatic substrate has an ortho, para-directing group), possibly because the electrophile is too bulky for effective attack at the ortho position. One of the most attractive features of the Friedel Crafts acylation is the deactivation of the product toward further substitution the acylation stops after one substitution
55 The Clemmensen Reduction: Synthesis of Alkylbenzenes 54 Acylbenzene can be reduced to alkylbenzene by treatment with aqueous HCl and amalgamated zinc (zinc treated with mercury salts). This two-step sequence can synthesize many alkylbenzenes that are impossible to make by direct alkylation.
56 Electrophilic Aromatic Substitution 55 Example
57 Problem #4 56
58 Nucleophilic Aromatic Substitution 57 Nucleophiles can displace halide ions from aryl halides, particularly if there are strong electron-withdrawing groups ortho or para to the halide.
59 Nucleophilic Aromatic Substitution 58 Mechanism
60 Nucleophilic Aromatic Substitution 59
61 Problem #5 60 Propose mechanisms and show the expected products of the following reactions.
62 Homework #1 61
63 Homework #2 62
64 Homework #3 62
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 informationChapter 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 informationOrganic 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 informationChapter 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 informationChapter 17: Reactions of Aromatic Compounds
1 Chapter 17: Reactions of Aromatic Compounds I. Introduction to Electrophilic Aromatic Substitution (EAS) A. General Mechanism II. Reactions of Electrophilic Aromatic Substitution A. Halogenation (E =
More information12/27/2010. 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 informationLecture 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 informationChapter 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 informationOrganic 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 informationChapter 12. Reactions of Arenes: Electrophilic Aromatic Substitution. Class Notes. A. The method by which substituted benzenes are synthesized
Chapter 12 Reactions of Arenes: Electrophilic Aromatic Substitution Chapter 12 suggested problems: 22, 23, 26, 27, 32, 33 Class Notes I. Electrophilic aromatic substitution reactions A. The method by which
More information16. 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 informationChapter 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 informationExamples of Substituted Benzenes
Organic Chemistry 5 th Edition Paula Yurkanis Bruice Examples of Substituted Benzenes Chapter 15 Reactions of Substituted Benzenes Irene Lee Case Western Reserve University Cleveland, OH 2007, Prentice
More informationElectrophilic 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 informationChapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution Paul D. Adams University of Arkansas Substitution Reactions of Benzene and Its Derivatives
More informationChapter 4 Part I. Aromatic Hydrocarbons Nomenclature, Structure, Properties, and an Introduction to Synthesis
Chapter 4 Part I Aromatic Hydrocarbons Nomenclature, Structure, Properties, and an Introduction to Synthesis The discovery of benzene In 1825, Michael Faraday isolated a pure compound of boiling point
More information08. 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 informationCHEM Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution (homework) W
CHEM 2425. Chapter 16. Chemistry of Benzene: Electrophilic Aromatic Substitution (homework) W Short Answer Exhibit 16-1 MATCH a structure or term from the following list with each description below. Place
More information16. 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 information16. 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 informationChemistry 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 informationOrganic 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 informationCHAPTER 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 information11/30/ 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 informationBenzenes & 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 informationTreatment of cyclooctatetrene with potassium gives you a dianion. Classify the starting material and product as aromatic, antiaromatic or
Treatment of cyclooctatetrene with potassium gives you a dianion. Classify the starting material and product as aromatic, antiaromatic or nonaromatic? 1 2 Classify cyclononatetrene and it s various ions
More informationREACTIONS OF AROMATIC COMPOUNDS
A STUDENT SHOULD BE ABLE TO: REACTIONS OF AROMATIC COMPOUNDS 1. Predict the product(s) of Electrophilic aromatic substitution (EAS): halogenation, sulfonation, nitration, Friedel- Crafts alkylation and
More informationORGANIC - BROWN 8E CH. 22- REACTIONS OF BENZENE AND ITS DERIVATIVES
!! www.clutchprep.com CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION GENERAL MECHANISM Benzene reacts with very few reagents. It DOES NOT undergo typical addition reactions. Why? If we can get benzene to
More informationBENZENE 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 informationCh 16 Electrophilic Aromatic Substitution
Ch 16 Electrophilic Aromatic Substitution Mechanism - Aromatic rings typically undergo substitution, where an H is replaced with an electrophile (E+). - The rings do not typically undergo addition across
More informationChapter 17 Aromati ti S u stit tit t u i tion Reactions
Chapter 17 Aromatic Substitution Reactions 1 17.1 Mechanism for Electricphilic Aromatic Substitution Arenium ion resonance stabilization 2 Example 1. Example 2. 3 Example 2. Mechanism of the nitration
More informationCh.16 Chemistry of Benzene: Electrophilic Aromatic Substitution
Ch.16 Chemistry of Benzene: Electrophilic Aromatic Substitution Electrophilic aromatic substitution: E + E + + Some electrophilic aromatic substitution: X N 2 S 3 R C R alogenation Nitration Sulfonation
More informationFundamentals of Organic Chemistry
Fundamentals of Organic Chemistry CHEM 109 For Students of Health Colleges Credit hrs.: (2+1) King Saud University College of Science, Chemistry Department CHEM 109 CHAPTER 3. AROMATIC HYDROCARBONS Aromatic
More informationChapter 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 informationH 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 informationElectrophilic 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 informationChapter 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 information4. 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 informationChapter 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 informationSURVEY ON ARYL COMPOUNDS
Journal of Plastic and Polymer Technology (JPPT) Vol. 1, Issue 1, Jun 2015, 111-132 TJPRC Pvt. Ltd SURVEY ON ARYL COMPOUNDS NAGHAM MAHMOOD ALJAMALI Organic Chemistry, Department of Chemistry, College of
More informationWilliam 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 informationChapter 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 informationSynthesis Using Aromatic Materials
Chapter 10 Synthesis Using Aromatic Materials ELECTROPHILIC AROMATIC SUBSTITUTION AND DIRECTED ORTHO METALATION Copyright 2018 by Nelson Education Limited 1 10.2 p Bonds Acting as Nucleophiles Copyright
More informationChapter 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 informationThe 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 informationCHEM 242 REACTIONS OF ARENES: CHAP 12 ASSIGN ELECTROPHILIC AROMATIC SUBSTITUTION A B C D E
CHEM 242 REACTIONS OF ARENES: CHAP 12 ASSIGN ELECTROPHILIC AROMATIC SUBSTITUTION 1. Consider carefully the mechanism of the following electrophilic aromatic substitution reaction and indicate which of
More informationElectrophilic 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 informationReactions 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 informationElectrophilic Aromatic Substitution
Lecture 12 Electrophilic Aromatic Substitution E E February 22, 2018 Electrophilic Aromatic Substitution Electrophilic aromatic substitution: a reaction in which a hydrogen atom on an aromatic ring is
More informationChapter 19: Aromatic Substitution Reactions
Chem A225 Notes Page 52 Chapter 19: Aromatic Substitution Reactions Topic One: lectrophilic Aromatic Substitution I. Introduction to lectrophilic Aromatic Substitution (AS) A. eneral Reaction Pattern B.
More informationChapter 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 informationChemistry 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 information11/26/ 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 informationI5 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 information432 CHAPTER 19. Solutions H H H. Base H O H S O H - SO 3 O S O O O
432 CAPTER 19 Solutions 19.1. Base 19.2. S S - S 3 S S S CAPTER 19 433 19.3. D S D S 3 D D D D D 19.4. S - 2 nitronium ion 2 2 2 2 19.5. c) + 434 CAPTER 19 19.6. Al 3 Al 3 Al 3 Al 3 Al 3 Al 3 CAPTER 19
More informationBenzene and Aromatic Compounds. Chapter 15 Organic Chemistry, 8 th Edition John McMurry
Benzene and Aromatic Compounds Chapter 15 Organic Chemistry, 8 th Edition John McMurry 1 Background Benzene (C 6 H 6 ) is the simplest aromatic hydrocarbon (or arene). Four degrees of unsaturation. It
More informationLearning Guide for Chapter 18 - Aromatic Compounds II
Learning Guide for Chapter 18 Aromatic Compounds. lectrophilic aromatic substitution ntroduction Mechanism Reagents and Products lectrophiles ffects of stituents FriedelCrafts alkylation and acylation
More informationModule9. Nuclear Magnetic Resonance Spectroscopy Nuclear Magnetic Resonance (NMR) spectroscopy - Chemical shift - Integration of signal area
1 CHEMISTRY 263 HOME WORK Lecture Topics: Module7. Hydrogenation of Alkenes The Function of the Catalyst - Syn and anti- addition Hydrogenation of Alkynes - Syn- addition of hydrogen: Synthesis of cis-alkenes
More informationAryl Halides. Structure
Aryl Halides Structure Aryl halides are compounds containing halogen attached directly to an aromatic ring. They have the general formula ArX, where Ar is phenyl, substituted phenyl. X= F,Cl,Br,I An aryl
More information5, Organic Chemistry-II (Reaction Mechanism-1)
Subject Chemistry Paper No and Title Module No and Title Module Tag 5, Organic Chemistry-II (Reaction Mechanism-1) 28, Arenium ion mechanism in electrophilic aromatic substitution, orientation and reactivity,
More informationCHEMISTRY 263 HOME WORK
Lecture Topics: CHEMISTRY 263 HOME WORK Module7: Hydrogenation of Alkenes Hydrogenation - syn and anti- addition - hydrogenation of alkynes - synthesis of cis-alkenes -synthesis of trans-alkenes Text sections:
More informationChapter 16- Chemistry of Benzene: Electrophilic Aromatic Substitution
Chapter 16- Chemistry of Benzene: Electrophilic Aromatic Substitution Ashley Piekarski, Ph.D. Substitution Reactions of Benzene and Its Derivatives Benzene is aroma%c What does aromatic mean? Reac9ons
More informationElectrophilic Aromatic Substitution (Aromatic compounds) Ar-H = aromatic compound 1. Nitration Ar-H + HNO 3, H 2 SO 4 Ar-NO 2 + H 2 O 2.
Electrophilic Aromatic Substitution (Aromatic compounds) Ar- = aromatic compound 1. Nitration Ar- + NO 3, 2 SO 4 Ar- + 2 O 2. Sulfonation Ar- + 2 SO 4, SO 3 Ar-SO 3 + 2 O 3. alogenation Ar- + X 2, Fe Ar-X
More information2016 Pearson Education, Inc. Isolated and Conjugated Dienes
2016 Pearson Education, Inc. Isolated and Conjugated Dienes 2016 Pearson Education, Inc. Reactions of Isolated Dienes 2016 Pearson Education, Inc. The Mechanism Double Bonds can have Different Reactivities
More informationChapter 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 informationChapter 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 informationBenzene 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 informationOption 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 informationReactions of Benzene Reactions of Benzene 1
Reactions of Benzene Reactions of Benzene 1 2 Halogenation of Benzene v Benzene does not react with Br 2 or Cl 2 unless a Lewis acid is present (a catalytic amount is usually enough) 3 v Mechanism v Mechanism
More informationAmines Reading Study Problems Key Concepts and Skills Lecture Topics: Amines: structure and nomenclature
Amines Reading: Wade chapter 19, sections 19-1-19-19 Study Problems: 19-37, 19-39, 19-40, 19-41, 19-44, 19-46, 19-47, 19-48, 19-51, 19-54 Key Concepts and Skills: Explain how the basicity of amines varies
More informationC h a p t e r N i n e t e e n Aromatics II: Reactions of Benzene & Its Derivatives
C h a p t e r N i n e t e e n Aromatics II: Reactions of Benzene & Its Derivatives Arenium ion from addition of tert-butyl cation to benzene (blue is δ+and red δ-) Note: Problems with italicized numbers
More informationChapter 24. Amines. Based on McMurry s Organic Chemistry, 7 th edition
Chapter 24. Amines Based on McMurry s Organic Chemistry, 7 th edition Amines Organic Nitrogen Compounds Organic derivatives of ammonia, NH 3, Nitrogen atom with a lone pair of electrons, making amines
More informationAmines. Amines are organic compounds containing a nitrogen functionality. primary secondary tertiary quaternary
Amines Amines are organic compounds containing a nitrogen functionality Depending upon the number of alkyl, or aryl, groups attached to nitrogen determines its classification, or order 2 primary secondary
More informationChem 263 Oct. 10, The strongest donating group determines where new substituents are introduced.
Chem 263 ct. 10, 2013 The strongest donating group determines where new substituents are introduced. N 2 N 3 2 S 4 + N 3 N 2 2 S 4 N 2 N 2 + 2 N N 2 N 3 2 S 4 N 2 2 N N 2 2,4,6-trinitrophenol picric acid
More information75. A This is a Markovnikov addition reaction. In these reactions, the pielectrons in the alkene act as a nucleophile. The strongest electrophile will
71. B SN2 stands for substitution nucleophilic bimolecular. This means that there is a bimolecular rate-determining step. Therefore, the reaction will follow second-order kinetics based on the collision
More informationFrost Circles a Great Trick
Aromatics Frost Circles a Great Trick Inscribe a polygon of the same number of sides as the ring to be examined such that one of the vertices is at the bottom of the ring The relative energies of the MOs
More informationMore 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 informationThere are two main electronic effects that substituents can exert:
Substituent Effects There are two main electronic effects that substituents can exert: RESONANCE effects are those that occur through the π system and can be represented by resonance structures. These
More informationChapter 16: Aromatic Compounds
Chamras Chemistry 106 Lecture otes xamination 2 Materials Chapter 16: Aromatic Compounds Benzene, the Most Commonly Known Aromatic Compound: The aromatic nature of benzene stabilizes it 36 kcal.mol 1.
More informationChapter 19: Amines. Introduction
Chapter 19: Amines Chap 19 HW: (be able to name amines); 37, 39, 41, 42, 44, 46, 47, 48, 53-55, 57, 58 Introduction Organic derivatives of ammonia. Many are biologically active. Chap 19: Amines Slide 19-2
More informationChemistry 14D Winter 2010 Exam 2 Page 1
Chemistry 14D Winter 2010 Exam 2 Page 1 1. (2) Circle the best statement of Markovnikov s rule. (a) When X adds to an alkene, the hydrogen of X becomes bonded to the alkene carbon that bears the least
More informationDAMIETTA 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 informationLecture 27 Organic Chemistry 1
CHEM 232 rganic Chemistry I at Chicago Lecture 27 rganic Chemistry 1 Professor Duncan Wardrop April 20, 2010 1 Self Test Question Nitrosonium (not nitronium) cations can be generated by treating sodium
More informationOrganic 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 informationDAMIETTA UNIVERSITY. Energy Diagram of One-Step Exothermic Reaction
DAMIETTA UNIVERSITY CHEM-103: BASIC ORGANIC CHEMISTRY LECTURE 5 Dr Ali El-Agamey 1 Energy Diagram of One-Step Exothermic Reaction The vertical axis in this graph represents the potential energy. The transition
More informationKey ideas: In EAS, pi bond is Nu and undergoes addition.
Objective 7. Apply addition and elimination concepts to predict electrophilic aromatic substitution reactions (EAS) of benzene and monosubstituted benzenes. Skills: Draw structure ID structural features
More informationBowman Chem 345 Lecture Notes by Topic. Electrophilic Aromatic Substitution (EAS):
lectrophilic Aromatic Substitution (AS): Aromatic rings have a tendency to be unreactive due to their inherent stability. However, aromatic rings can react given the right incentives. ne way, they can
More informationTOK: 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 informationHour Examination # 1
CEM 347 rganic Chemistry II Spring 2015 Exam # 1 Solutions Key Page 1 of 11 CEM 347 rganic Chemistry II Spring 2015 Instructor: Paul Bracher our Examination # 1 Wednesday, February 11 th, 2015 6:00 8:00
More informationChapter 22 Amines. Nomenclature Amines are classified according to the degree of substitution at nitrogen.
CH. 22 Chapter 22 Amines Amines are very important in biological chemistry. Most of the bases in biological acid-base reactions are amines. They are also very important nucleophiles in biochemical reactions.
More informationSeminar_3. 1. Substituded derivatives of benzene and their nomenclature
1. Substituded derivatives of benzene and their nomenclature 2. Reactions of arenes. Electrophilic aromatic substitutions 3. Activating substituents. Orientation in the aromatic ring Seminar_3 TEST - Aromatic
More informationOrganic Chemistry Lecture 2 - Hydrocarbons, Alcohols, Substitutions
ALKANES Water-insoluble, low density C-C single bonds Higher MW -> higher BP, higher MP Branching -> lower BP, higher MP Forms cycloalkanes which can have ring strain Cyclohexane: chair vs. boat configuration
More information15.10 Effect of Substituents on Reactivity and Orientation
15.10 ffect of Substituents on Reactivity and Orientation Z NO 3 2 SO 4 Z Z Z + + o- p- m- Z O Me CN o(%) 40 59 30 6 17 p(%) 60 37 69
More informationChem 263 Oct. 4, 2016
Chem 263 ct. 4, 2016 ow to determine position and reactivity: Examples The strongest donating group wins: 2 3 2 S 4 + 3 2 2 S 4 2 2 + 2 2 3 2 S 4 2 2 2 2,4,6-trinitrophenol picric acid This reactivity
More informationClass XII: Chemistry Chapter 13: Amines Top concepts
Class XII: Chemistry Chapter 13: Amines Top concepts 1. Amines are regarded as derivatives of ammonia in which one, two or all three hydrogen atoms are replaced by alkyl or aryl group 2. Classification
More information240 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 informationKOT 222 Organic Chemistry II
KOT 222 Organic Chemistry II Course Objectives: 1) To introduce the chemistry of alcohols and ethers. 2) To study the chemistry of functional groups. 3) To learn the chemistry of aromatic compounds and
More informationChapter 10: Carboxylic Acids and Their Derivatives
Chapter 10: Carboxylic Acids and Their Derivatives The back of the white willow tree (Salix alba) is a source of salicylic acid which is used to make aspirin (acetylsalicylic acid) The functional group
More informationCOURSE OBJECTIVES / OUTCOMES / COMPETENCIES.
COURSE OBJECTIVES / OUTCOMES / COMPETENCIES. By the end of the course, students should be able to do the following: See Test1-4 Objectives/Competencies as listed in the syllabus and on the main course
More informationChapter 9 Aldehydes and Ketones Excluded Sections:
Chapter 9 Aldehydes and Ketones Excluded Sections: 9.14-9.19 Aldehydes and ketones are found in many fragrant odors of many fruits, fine perfumes, hormones etc. some examples are listed below. Aldehydes
More information