The Electronic Theory of Organic Reactions,
|
|
|
- Gilbert Sims
- 5 years ago
- Views:
Transcription
1 The Electronic Theory of Organic Reactions,
2 A New Set of Issues for Organic Chemists Can we explain chemical change? What causes tautomerism? O O OH O OEt OEt Why do conjugated systems behave so strangely? Are physical methods relevant to organic chemistry? Reductionism: How should chemistry be affected by the new model of the atom?
3 Robert Robinson ( )
4 Robinson and Residual Valences Br Br Lapworth s polarities Thiele s dotted affinities Polarization of bonds in the intermediate complex No extra affinities, but split or fractional bonds.
5 Robinson and Residual Valences Gertrude Maud Robinson and Robert Robinson, Researches on Pseudo-Bases. Part II. Note on Some Berberine Derivatives and Remarks on the Mechanism of the Condensation Reactions of Pseudo-Bases, Journal of the Chemical Society, 111 (1917):
6 Robert Robinson, The Conjugation of Partial Valencies, Manchester Memoirs, 64 (1920),
7 Robert Robinson, The Conjugation of Partial Valencies, Manchester Memoirs, 64 (1920),
8 Robert Robinson, The Conjugation of Partial Valencies, Manchester Memoirs, 64 (1920),
9 Bernard Flürscheim ( ) Studied with Thiele and Werner Royal Institution, London ( ; ) Private laboratory In carbon chains, strong and weak links would alternate. Not charges, but affinities alternate.
10 Flürscheim s Affinity Demand Model Alternation of quantity of affinity Affinity is continuously divisible (partly bound, partly free) Atoms that can increase valency the most create the most affinity demand Works well to explain the directive ability of most groups on aromatic rings. OH O N O
11 William Ogilvy Kermack and Robert Robinson, An Explanation of the Property of Induced Polarity of Atoms and an Interpretation of the Theory of Partial Valencies on an Electronic Basis, Journal of the Chemical Society, 121 (1922),
12 William Ogilvy Kermack and Robert Robinson, An Explanation of the Property of Induced Polarity of Atoms and an Interpretation of the Theory of Partial Valencies on an Electronic Basis, Journal of the Chemical Society, 121 (1922),
13 Christopher Kelk Ingold ( ) 1918: PhD University College, London (Jocelyn Thorpe) 1920: Postdoctoral work with Thorpe 1924: University of Leeds 1930: University College, London Influenced by Flürscheim s affinity demand model
14 Christopher Ingold, The Nature of the Alternating Effect in Carbon Chains. Part I. The Directive Influence of the Nitroso-Group in Aromatic Substitution, Journal of the Chemical Society, 127 (1925):
15 NO Ortho product NO Para product Robinson s Response to Ingold s Results
16 Christopher Ingold and Edith Hilda Ingold, The Nature of the Alternating Effect in Carbon Chains. Part II. The Directing Influence of the -Methoxyvinyl Group in Aromatic Substitution, Journal of the Chemical Society, 127 (1925):
17 Eric Holmes and Christopher Ingold, The Nature of the Alternating Effect in Carbon Chains. Part III. A Comparative Study of the Directive Efficiencies of Oxygen and Nitrogen Atoms in Aromatic Substitution, Journal of the Chemical Society, 127 (1925):
18 Eric Holmes and Christopher Ingold, The Nature of the Alternating Effect in Carbon Chains. Part III. A Comparative Study of the Directive Efficiencies of Oxygen and Nitrogen Atoms in Aromatic Substitution, Journal of the Chemical Society, 127 (1925):
19 James Allan, Albert Edward Oxford, Robert Robinson and John Charles Smith, The Relative Directive Powers of Groups of the Forms RO and RR N in Aromatic Substitution. Part IV. A Discussion of the Observations Recorded in Parts I, II, and III, Journal of the Chemical Society, 129 (1926):
20 James Allan, Albert Edward Oxford, Robert Robinson and John Charles Smith, The Relative Directive Powers of Groups of the Forms RO and RR N in Aromatic Substitution. Part IV. A Discussion of the Observations Recorded in Parts I, II, and III, Journal of the Chemical Society, 129 (1926):
21 James Allan, Albert Edward Oxford, Robert Robinson and John Charles Smith, The Relative Directive Powers of Groups of the Forms RO and RR N in Aromatic Substitution. Part IV. A Discussion of the Observations Recorded in Parts I, II, and III, Journal of the Chemical Society, 129 (1926):
22 James Allan, Albert Edward Oxford, Robert Robinson and John Charles Smith, The Relative Directive Powers of Groups of the Forms RO and RR N in Aromatic Substitution. Part IV. A Discussion of the Observations Recorded in Parts I, II, and III, Journal of the Chemical Society, 129 (1926):
23 Christopher K. Ingold and E. H. Ingold, The Nature of the Alternating Effect in Carbon Chains. Pt. V. A Discussion of Aromatic Substitution With Special Reference to the Respective Roles of Polar and Non-Polar Dissociation; and a Further Study of the Relative Directive Efficiencies of Oxygen and Nitrogen, Journal of the Chemical Society, 129 (1926):
24 Christopher K. Ingold and E. H. Ingold, The Nature of the Alternating Effect in Carbon Chains. Pt. V. A Discussion of Aromatic Substitution With Special Reference to the Respective Roles of Polar and Non-Polar Dissociation; and a Further Study of the Relative Directive Efficiencies of Oxygen and Nitrogen, Journal of the Chemical Society, 129 (1926):
25 Ingold s New System for Organic Chemistry Series of Annual Reports from Inconsistencies between older systems removed by new the new scheme anionoid > Nucleophilic (all bases) cationoid -> Electrophilic (all acids) Inductive effect unequal sharing of electron pairs. Tautomeric effect electronic reinterpretation of the Flurscheim model of residual affinity. The tautomeric effect is not permanent but an activated form, resulting in a measurable dipole, represented by the curved arrow. Unification of aromatic and aliphatic organic chemistry Principles of an Electronic Theory of Organic Reactions, Chemical Reviews, 15 (1934): Structure and Mechanism in Organic Chemistry, 1953
26 Edward Hughes ( ) 1920s: Bangor University, North Wales 1930: Postdoctoral with Ingold : Bangor 1948: Second chair for chemistry at University College, London Learned reaction kinetics techniques with Kennedy Orton at Bangor
27 Classification of Reaction Mechanisms by Chemical Kinetics Reaction kinetics show bimolecular or unimolecular reactions The rate kinetics indicate the molecularity of the reaction, and its mechanism (bond formation and cleavage). Lewis bond formulas suggest the rearrangement of bonds S N 1, S N 2, E2 mechanisms suggested in 1933 E1 found by Hughes in 1935 Any given reaction can proceed in one or more ways, according to conditions of the reaction. CN OEt KCN EtOK Cl H 2 SO 4 (CH 3 ) 3 OK
28 The Walden Inversion (Paul Walden, ) l-malic acid Ag 2 O l-chlorosuccinic acid PCl 5 KOH PCl 5 KOH d-chlorosuccinic acid Ag 2 O d-malic acid Where does the inversion take place?
29 Explaining the Walden Inversion, Mechanism revealed through kinetic studies Every case of S N 2 substitution leads to inversion. Inversion requires breaking the bond at the asymmetric center. Optical inversion (preserved asymmetry) always accompanies optical inversion. Racemization always accompanies unimolecular substitutions (production of an symmetrical, planar carbonium ion)
30 Characteristics of Ingold s Chemistry Creation of a new systematic language that reflects theory. Appropriation and renaming of older concepts. Use of physical methods - Chemical kinetics vs. mechanism - Dipoles - Effect of isotopic labelling on rates - Dissociation constants Anthropomorphic and economic metaphors: nucleophilic and electrophilic It is a commonplace of electronic theories that chemical change is an electrical transaction and that reagents act by virtue of a constitutional affinity, either for electrons or for atomic nuclei. When, for example, an electron-seeking reagent attacks some center in an organic molecule,... reaction will supervene provided that the center can supply electrons. to the requisite extent.... Sharing economizes electrons.
31 Further Reading William H. Brock, The Chemical Tree: A History of Chemistry, New York: Norton, 2000, chapters 13 and 14. Martin D. Saltzman, The Robinson-Ingold Controversy: Precedence in the Electronic Theory of Organic Reactions, Journal of Chemical Education, 50 (1980): J. Shorter, Electronic Theories of Organic Chemistry: Robinson and Ingold, Natural Product Reports, 4 (1987): Mary Jo Nye, From Chemical Philosophy to Theoretical Chemistry: Dynamics of Matter and Dynamics of Disciplines, , Berkeley: University of California Press, 1993.
Learn- More. Weblinks. PAPER 5: Organic Chemistry- II MODULE 23 : SE2 Reactions
Learn- More Weblinks q http://www.scribd.com/doc/25905271/aliphatic-electrophilic-substitution-reactions q http://en.wikipedia.org/wiki/electrophilic_substitution q http://www.scribd.com/doc/76229481/electrophilic-substitution
PAPER No. 05: TITLE: ORGANIC CHEMISTRY-II MODULE No. 12: TITLE: S N 1 Reactions
Subject hemistry Paper o and Title Module o and Title Module Tag 05, ORGAI EMISTRY-II 12, S 1 Reactions E_P5_M12 EMISTRY PAPER o. 05: TITLE: ORGAI EMISTRY-II TABLE OF OTETS 1. Learning Outcomes 2. Introduction
Chemistry 123: Physical and Organic Chemistry Topic 1: Organic Chemistry
Concept Check: Topic 1: Conformation Winter 2009 Page 112 Concept Check: Topic 1: Conformation Winter 2009 Page 113 1 STEREOCHEMISTRY Winter 2009 Page 114 We have already covered two kinds of isomerism:
Study of Chemical Reactions
Study of Chemical Reactions Introduction to Mechanisms There are four different types of organic reactions: Additions Eliminations Substitutions Rearrangements 149 Addition Reactions Occur when 2 reactants
Glendale Community College Chemistry 105 Exam. 3 Lecture Notes Chapters 6 & 7
Sevada Chamras, Ph.D. Glendale Community College Chemistry 105 Exam. 3 Lecture Notes Chapters 6 & 7 Description: Examples: 3 Major Types of Organic Halides: 1. Alkyl Halides: Chapter 6 (Part 1/2) : Alkyl
There 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
Chapter 9. Nucleophilic Substitution and ß-Elimination
Chapter 9 Nucleophilic Substitution and ß-Elimination Nucleophilic Substitution Nucleophile: From the Greek meaning nucleus loving. A molecule or ion that donates a pair of electrons to another atom or
Week 4. Even harder stuff!
Week 4 Even harder stuff! Focus: SN1 and SN2 Two organic reactions Learn about two basic pathways for how these reactions happen Focus on stereochemistry Focus: SN1 and SN2 You need a couple of things
CH 3 OCH 3. Question 4. Provide the missing reactants for the following Diels-Alder reaction. heat
CHEMISTRY 234, MIDTERM #2 PRACTICE TEST #1-3 - NAME Question 3 For each reaction 1) Provide the missing reagents/conditions or major organic products as appropriate 2) State whether the OVERALL reaction
Reaction mechanisms offer us insights into how reactions work / how molecules react with one another.
Introduction 1) Lewis Structures 2) Representing Organic Structures 3) Geometry and Hybridization 4) Electronegativities and Dipoles 5) Resonance Structures (a) Drawing Them (b) Rules for Resonance 6)
Basic Organic Chemistry Course code : CHEM (Pre-requisites : CHEM 11122)
Basic Organic Chemistry Course code : CHEM 12162 (Pre-requisites : CHEM 11122) Chapter 01 Mechanistic Aspects of S N2,S N1, E 2 & E 1 Reactions Dr. Dinesh R. Pandithavidana Office: B1 222/3 Phone: (+94)777-745-720
CHE1502. Tutorial letter 201/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry CHE1502/201/1/2016
CE1502/201/1/2016 Tutorial letter 201/1/2016 General Chemistry 1B CE1502 Semester 1 Department of Chemistry This tutorial letter contains the answers to the questions in assignment 1. FIRST SEMESTER: KEY
23.5 Nucleophilic Substitution in Nitro-Substituted Aryl Halides
23.5 Nucleophilic Substitution in Nitro-Substituted Aryl alides nitro-substituted aryl halides do undergo nucleophilic aromatic substitution readily Cl OC 3 + NaOC 3 C 3 O 85 C + NaCl NO 2 NO 2 (92%) Effect
OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2018
OChem 1 Mechanism Flashcards Dr. Peter Norris, 2018 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons
OChem 1 Mechanism Flashcards. Dr. Peter Norris, 2015
OChem 1 Mechanism Flashcards Dr. Peter Norris, 2015 Mechanism Basics Chemical change involves bonds forming and breaking; a mechanism describes those changes using curved arrows to describe the electrons
CHEMISTRY 102B Hour Exam III. Dr. D. DeCoste T.A. Show all of your work and provide complete answers to questions 16 and (45 pts.
CHEMISTRY 102B Hour Exam III April 28, 2016 Dr. D. DeCoste Name Signature T.A. This exam contains 17 questions on 8 numbered pages. Check now to make sure you have a complete exam. You have one hour and
REACTION AND SYNTHESIS REVIEW
REACTION AND SYNTHESIS REVIEW A STUDENT SHOULD BE ABLE TO PREDICT PRODUCTS, IDENTIFY REACTANTS, GIVE REACTION CONDITIONS, PROPOSE SYNTHESES, AND PROPOSE MECHANISMS (AS LISTED BELOW). REVIEW THE MECHANISM
PAPER No. 5: REACTION MECHANISM MODULE No. 2: Types of Organic Reaction Mechanisms
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper No. 5:Organic Chemistry-II Module No. 2: Overview of different types of Organic Reaction Mechanisms CHE_P5_M2 TABLE OF CONTENTS
Nucleophiles: nucleus liking species. Nucleophilic substitution
1 Nucleophiles: nucleus liking species Electron rich Possesses negative charge or non bonded valence electrons Large abundance of nucleophiles in the environment (water itself is a nucleophile) Nucleophilic
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
11. Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations Based on McMurry s Organic Chemistry, 6 th edition 2003 Ronald Kluger Department of Chemistry University of Toronto Alkyl Halides
Preparation of Alkyl Halides, R-X. Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): R + X X 2.
Preparation of Alkyl alides, R-X Reaction of alkanes with Cl 2 & Br 2 (F 2 is too reactive, I 2 is unreactive): UV R + X 2 R X or heat + X This mechanism involves a free radical chain reaction. A chain
CHAPTER 7. Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination
CHAPTER 7 Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination 7-1 Solvolysis of Tertiary and Secondary Haloalkanes The rate of S N 2 reactions decrease dramatically
Chapter 8. Substitution reactions of Alkyl Halides
Chapter 8. Substitution reactions of Alkyl Halides There are two types of possible reaction in organic compounds in which sp 3 carbon is bonded to an electronegative atom or group (ex, halides) 1. Substitution
Learning Guide for Chapter 11 - Alkenes I
Learning Guide for Chapter 11 - Alkenes I I. Introduction to alkenes - p 1 bond structure, classifying alkenes, reactivity, physical properties, occurrences and uses, spectroscopy, stabilty II. Unsaturation
Chem 3719 Klein Chapter Practice Problems
Chem 379 Klein Chapter Practice Problems Dr. Peter Norris, 208 Klein Chapter Problems : Review of General Chemistry. Draw viable structures for molecules with the following molecular formulae. Remember
3.8 Aldehydes and ketones
3.8 Aldehydes and ketones Introduction: p's to p's Like the alkenes, the carbonyl group consists of a s bond and a p bond between the carbon and oxygen: Oxygen is more electronegative than carbon meaning
Chapter 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
Chapter 8 Alkyl Halides and Elimination Reactions
Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai i Chapter 8 Alkyl Halides and Elimination Reactions Prepared by Rabi Ann Musah State University of New York at Albany Copyright
Chapter 9. Lewis Theory-VSEPR Valence Bond Theory Molecular Orbital Theory
Chapter 9 Lewis Theory-VSEPR Valence Bond Theory Molecular Orbital Theory Problems with Lewis Theory Lewis theory generally predicts trends in properties, but does not give good numerical predictions.
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320
Nuggets of Knowledge for Chapter 17 Dienes and Aromaticity Chem 2320 I. Isolated, cumulated, and conjugated dienes A diene is any compound with two or C=C's is a diene. Compounds containing more than two
Mechanisms of Ion Fragmentation (McLafferty Chapter 4) Business Items
Mechanisms of Ion Fragmentation (McLafferty Chapter 4) CU- Boulder CHEM 5181 Mass Spectrometry & Chromatography Prof. Jose-Luis Jimenez 1 Business Items Last real lecture is today Material from today,
2311A and B Practice Problems to help Prepare for Final from Previous Marder Exams.
2311A and B Practice Problems to help Prepare for Final from Previous Marder Exams. Disclaimer.: Use only to help learn what you need to know and don t expect the final to be in the same form. 1 1. Short
Course Goals for CHEM 202
Course Goals for CHEM 202 Students will use their understanding of chemical bonding and energetics to predict and explain changes in enthalpy, entropy, and free energy for a variety of processes and reactions.
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
Reactions of Alkyl Halides with Nucleophiles and Bases a substitution reaction
Reactions of Alkyl Halides with Nucleophiles and Bases a substitution reaction Nucleophilic substitution and base induced elimination are among most widely occurring and versatile reaction types in organic
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
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
Polarity main concepts
POLARITY Polarity main concepts A polar molecule has opposite charged ends (+ & -) The polarity of a bond is the result of a difference in electronegativity between the two bonded atoms A molecule can
An Overview of Organic Reactions. Reaction types: Classification by outcome Most reactions produce changes in the functional group of the reactants:
An Overview of Organic Reactions Reaction types: Classification by outcome Most reactions produce changes in the functional group of the reactants: 1. Addition (forward) Gain of atoms across a bond Example:
2. Examining the infrared spectrum of a compound allows us to:
CHEM 204 2010 Ass. 1 Problem 1. The amount of energy in infrared light corresponds to: a. the amount of energy needed to promote one electron from a bonding to an antibonding molecular orbital b. the amount
Module No and Title. PAPER No: 5 ; TITLE : Organic Chemistry-II MODULE No: 25 ; TITLE: S E 1 reactions
Subject Chemistry Paper No and Title Module No and Title Module Tag 5; Organic Chemistry-II 25; S E 1 reactions CHE_P5_M25 TABLE OF CONTENTS 1. Learning Outcomes 2. Introduction 3. S E 1 reactions 3.1
Lab: Model Building with Covalent Compounds - Introduction
Name Date Period # Lab: Model Building with Covalent Compounds - Introduction Most of our learning is in two dimensions. We see pictures in books and on walls and chalkboards. We often draw representations
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
Ch 10 Chemical Bonding, Lewis Structures for Ionic & Covalent Compounds, and Predicting Shapes of Molecules
Fructose Water Ch 10 Chemical Bonding, Lewis Structures for Ionic & Covalent Compounds, and Predicting Shapes of Molecules Carbon Dioxide Ammonia Title and Highlight TN Ch 10.1 Topic: EQ: Right Side NOTES
Organic Chemistry. Alkenes (2)
For updated version, please click on http://ocw.ump.edu.my Organic Chemistry Alkenes (2) by Dr. Seema Zareen & Dr. Izan Izwan Misnon Faculty Industrial Science & Technology seema@ump.edu.my & iezwan@ump.edu.my
5, 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,
Physical Properties: Structure:
Nomenclature: Functional group suffix = -ol Functional group prefix = hydroxy- Primary, secondary or tertiary? Alcohols are described as primary (1 o ), secondary (2 o ) or tertiary (3 o ) depending on
Chapter 8. Basic Concepts of Chemical Bonding
Chapter 8. Basic Concepts of Chemical Bonding 8.1 Lewis Symbols and the Octet Rule When atoms or ions are strongly attracted to one another, we say that there is a chemical bond between them. In chemical
Section 8.1 The Covalent Bond
Section 8.1 The Covalent Bond Apply the octet rule to atoms that form covalent bonds. Describe the formation of single, double, and triple covalent bonds. Contrast sigma and pi bonds. Relate the strength
ORGANIC CHEMISTRY. Meaning of Organic?
ORGANIC CHEMISTRY Meaning of Organic? Initially scientists believed there was a special force in living organisms -this was assumed the unique component of organic material In 1828 Wöhler synthesized urea
Nucleophile. Reaction Intermediate. Introduction to Reaction mechanisms. Definitions 2/25/2012
Introduction to Reaction mechanisms Definition A reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. It is also a detailed description of the
6-2 This exercise is worked out on page 220 as "Working with Concepts".
Copyright 2009 James K Whitesell 6-1 Although we can approach this exercise from a chemical perspective, one can also teach a non-chemist how to derive the answer once the name of the starting material
Unit title: Organic Chemistry
Unit title: Organic Chemistry Unit code: R/601/0352 QCF level: 4 Credit value: 15 Aim This unit develops the principles and practical techniques of organic chemistry. Rationalisation of structure and bonding
ORGANIC - BROWN 8E CH.4 - ACIDS AND BASES.
!! www.clutchprep.com CONCEPT: FREE ENERGY DIAGRAMS Atoms save energy by forming bonds. Free energy diagrams show overall changes in potential energy during reactions. Free energy diagrams give us information
Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid
![Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid](/thumbs/95/123929992.jpg "Acid-Base -Bronsted-Lowry model: -Lewis model: -The more equilibrium lies to the right = More [H 3 O + ] = Higher K a = Lower pk a = Stronger acid")
Revision Hybridisation -The valence electrons of a Carbon atom sit in 1s 2 2s 2 2p 2 orbitals that are different in energy. It has 2 x 2s electrons + 2 x 2p electrons are available to form 4 covalent bonds.
Section Practice Exam II Solutions
Paul Bracher Chem 30 Section 7 Section Practice Exam II s Whether problems old r problems new, You d better practice, r you ll fail exam II. -- Anonymous TF Problem 1 a) Rank the following series of electrophiles
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
Chapter 2: Acids and Bases
1. Which of the following statements is a correct definition for a Brønsted-Lowry acid? A) Proton acceptor C) Electron pair acceptor B) Electron pair donor D) Proton donor 2. Which of the following statements
Chapter 3 Acids and Bases. The Curved-Arrow Notation
Organic Chemistry, 5th ed. Marc Loudon Chapter 3 Acids and Bases. The Curved-Arrow Notation Eric J. Kantorows ki California Polytechnic State University San Luis Obispo, CA Chapter 3 Overview 3.1 Lewis
2016 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
Chapter 8. Bonding: General Concepts
Chapter 8 Bonding: General Concepts Chapter 8 Table of Contents 8.1 Types of Chemical Bonds 8.3 Bond Polarity and Dipole Moments 8.5 Energy Effects in Binary Ionic Compounds 8.6 Partial Ionic Character
Ethers can be symmetrical or not:
Chapter 14: Ethers, Epoxides, and Sulfides 175 Physical Properties Ethers can be symmetrical or not: linear or cyclic. Ethers are inert and make excellent solvents for organic reactions. Epoxides are very
C h a p t e r S e v e n : Haloalkanes: Nucleophilc Substitution and Elimination Reactions S N 2
C h a p t e r S e v e n : Haloalkanes: Nucleophilc Substitution and Elimination Reactions S N 2 CHM 321: Summary of Important Concepts Concepts for Chapter 7: Substitution Reactions I. Nomenclature of
Organic Chemistry I Dr Alex Roche Organic chemistry is the chemistry of Carbon and its compounds. Organic molecules constitute the essence of life (fats, sugars, proteins, DNA), and also permeate our everyday
Chemistry 234 Exam 1 (Gray) The Periodic Table
ame: Last First MI Chemistry 234 Exam 1 (Gray) Summer 2017 Dr. J. sbourn Instructions: The first 21 questions of this exam should be answered on the provided Scantron. You must use a pencil for filling
Reactions SN2 and SN1
Reactions SN2 and SN1 Reactivity: Functional groups can be interconverted using a great variety of reagents. Millions of organic molecules have been synthesized via a series of functional-group interconversions.
Chem 112A: Final Exam
Chem 112A: Final Exam December 15th, 2010 Please provide all answers in the spaces provided. You are not allowed to use a calculator for this exam, but you may use molecular model kits. nly cyclohexane
Janice Gorzynski Smith University of Hawai i. Chapter 7. Modified by Dr. Juliet Hahn
Organic Chemistry, Fifth Edition Janice Gorzynski Smith University of Hawai i Chapter 7 Modified by Dr. Juliet Hahn Copyright 2017 McGraw-Hill Education. All rights reserved. No reproduction or distribution
75. 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
Chapter 3 An Introduction to Organic Reactions: Acids and Bases
There are 4 types of Organic Reactions Chapter 3 An Introduction to Organic Reactions: SUBSTITUTION: ADDITION: X Y + A X A + Y Example Example A B + X Y A B X Y ELIMINATION There are 4 Types of Organic
Chapter 10 Lecture Outline
Organic Chemistry, Fifth Edition Janice Gorzynski Smith University of Hawai i Chapter 10 Lecture Outline Modified by Dr. Juliet Hahn Copyright 2017 McGraw-Hill Education. All rights reserved. No reproduction
ORGANIC - CLUTCH CH. 3 - ACIDS AND BASES.
!! www.clutchprep.com CONCEPT: OVERVIEW OF CHEMICAL REACTIONS There are 4 types of common chemical reactions that we need to be familiar with in organic chemistry 1. Acid-Base Reactions: Two molecules
Structure and Preparation of Alkenes: Elimination Reactions
Structure and Preparation of Alkenes: Elimination Reactions Alkene Nomenclature First identify the longest continuous chain that includes the double bond. Replace the -ane ending of the corresponding unbranched
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.
Electrophiles are attracted to the π bond Addition sees a π bond replaced with a σ bond There are many different types of addition reactions:
Nucleophiles and Electrophiles Nucleophiles are the atoms that donates the electron pairs and is added to the molecules (In the example above this is the CN) Electrophiles are the atoms that seek electron
Chapter 8 Outline: Alkenes: Structure and Preparation via β-elimination
Chapter 8 Outline: Alkenes: Structure and Preparation via β-elimination 1. What is β elimination? 2. Alkenes: structure, steroisomerism and stability 3. Elimination Reactions o E2 Mechanism o E1 Mechanism
Homework - Review of Chem 2310
omework - Review of Chem 2310 Chapter 1 - Atoms and Molecules Name 1. What is organic chemistry? 2. Why is there an entire one year course devoted to the study of organic compounds? 3. Give 4 examples
Synthesis 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
Upon successful completion of this course, the student will be able to:
CHEM 244 PRINCIPLES OF ORGANIC CHEMISTRY I FOR CHEMICAL ENGINEERING STUDENTS, COLLEGE OF ENGINEERING PRE-REQUISITES COURSE; CHEM 101 CREDIT HOURS; 2 (2+0) Dr. Mohamed El-Newehy Chemistry Department, College
CHEMISTRY - BURDGE-ATOMS FIRST 3E CH.6 - REPRESENTING MOLECULES.
!! www.clutchprep.com CONCEPT: ELECTRON-DOT SYMBOLS Before we look at the first two bonding models, we have to figure out how to depict the valence electrons of bonding atoms. In the electron-dot symbol,
p Bonds as Electrophiles
Chapter 7 p Bonds as Electrophiles REACTIONS OF CARBONYLS AND RELATED FUNCTIONAL GROUPS Copyright 2018 by Nelson Education Limited 1 7.2.1 Orbital structure of the carbonyl group Because oxygen is more
1.10 Structural formulas
1.10 Structural formulas It shows which atoms are bonded to which. There are two types of structural formulas, complete Lewis structures and condensed structural formulas. In addition, there are several
Fundamentals of. Organic Chemistry. for. [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester
![Fundamentals of. Organic Chemistry. for. [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester](/thumbs/87/95891041.jpg "Fundamentals of. Organic Chemistry. for. [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester")
Fundamentals of Organic Chemistry for [Second Year B.Sc. (Main) Students of M.G. University, Kerala] III Semester (This Book is an outcome of Modern Organic Chemistry by M.K. Jain & S.C. Sharma duly recommended
Polarity main concepts
POLARITY Polarity main concepts 1. A polar molecule has opposite charged ends (+ & -) 2. The polarity of a bond is the result of a difference in electronegativity between the two bonded atoms 3. A molecule
Molecular Geometry & Polarity
Molecular Geometry & Polarity Learn Shapes you will Because the physical and chemical properties of compounds are tied to their structures, the importance of molecular geometry can not be overstated. Localized
California State Polytechnic University, Pomona Chem 315. Exam Points 1. Nomenclature (1) 30
hem 315 Final Exam Fall, 2007 Beauchamp ame: Topic Total Points Exam Points 1. omenclature (1) 30 redit 2. Relative rder of Reactivity 20 3. Reactions Page, using reactions learned thus far (30) 30 4.
CH 222 Chapter Seven Concept Guide
CH 222 Chapter Seven Concept Guide 1. Lewis Structures Draw the Lewis Dot Structure for cyanide ion, CN -. 1 C at 4 electrons = 4 electrons 1 N at 5 electrons = 5 electrons -1 charge = + 1 electron Total
Chemistry 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
CHEMISTRY Matter and Change Section 8.1 The Covalent Bond
CHEMISTRY Matter and Change Section Chapter 8: Covalent Bonding CHAPTER 8 Table Of Contents Section 8.2 Section 8.3 Section 8.4 Section 8.5 Naming Molecules Molecular Structures Molecular Shapes Electronegativity
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
Exam (6 pts) Show which starting materials are used to produce the following Diels-Alder products:
Exam 1 Name CHEM 212 1. (18 pts) Complete the following chemical reactions showing all major organic products; illustrate proper stereochemistry where appropriate. If no reaction occurs, indicate NR :
Benzene 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
Practice Hour Examination # 1-1
CHEM 346 Organic Chemistry I Fall 2013 Practice Hour Examination # 1-1 Solutions Key Page 1 of 12 CHEM 346 Organic Chemistry I (for Majors) Instructor: Paul J. Bracher Practice Hour Examination # 1-1 Monday,
CHEMISTRY 112A FALL 2015 FINAL EXAM DECEMBER 16, 2015 NAME- WRITE BIG STUDENT ID: SECTION AND/OR GSI IF YOU ARE IN THE LABORATORY COURSE:
CEMISTRY 112A FALL 2015 FINAL EXAM DECEMBER 16, 2015 NAME- WRITE BIG STUDENT ID: SECTIN AND/R GSI IF YU ARE IN TE LABRATRY CURSE: You will have 2 hours 45 minutes minutes in which to work. Problem Points
Chapter 3 Acids and Bases"
Chapter 3 Acids and Bases BrØnsted-Lowry Acids and Bases A BrØnsted-Lowry acid is a proton donor. A BrØnsted-Lowry base is a proton acceptor. H + = proton Acids and Bases Reactions of BrØnsted-Lowry Acids
Bonding Test pg 1 of 4 Name: Pd. Date:
Bonding Test pg 1 of 4 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) How many electrons are shared in a single covalent bond? 1. A) 2 B) 3 C)
Chemistry for the gifted and talented 45
45 Curly arrows and stereoselectivity in organic reactions Student worksheet: CDROM index 23SW Discussion of answers: CDROM index 23DA Topics Curly arrows, the mechanism for esterification, inversion during
Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions
Chapter 6: Organic Halogen Compounds; Substitution and Elimination Reactions Halogen compounds are important for several reasons. Simple alkyl and aryl halides, especially chlorides and bromides, are versatile
Organic Reactions and Mechanisms
Organic Reactions and Mechanisms Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution
Key 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