p Bonds as Nucleophiles
|
|
- Blanche Lambert
- 5 years ago
- Views:
Transcription
1 Chapter 8 p Bonds as Nucleophiles REACTIONS OF ALKENES, ALKYNES, DIENES, AND ENOLS Copyright 2018 by Nelson Education Limited 1
2 8.2.1 Orbital structure of alkenes Geometry: Electrostatic potential: Electron-rich p bond can act as a nucleophile. Copyright 2018 by Nelson Education Limited 2
3 8.2.2 Electrophilic addition reactions Addition of hydrogen halides Copyright 2018 by Nelson Education Limited 3
4 Mechanism: Step 1: Step 2: Copyright 2018 by Nelson Education Limited 4
5 8.3 Carbocation Formation and Function Copyright 2018 by Nelson Education Limited 5
6 8.3.1 Energy changes control reactivity Copyright 2018 by Nelson Education Limited 6
7 8.3.2 Regioselectivity in electrophilic addition reactions Regioisomers: constitutional isomers formed when a reaction takes place at different locations in a molecule Regioselectivity: formation of one regioisomer in preference to others regioisomers major product Copyright 2018 by Nelson Education Limited 7
8 Carbocation formation is the rate-determining step. Copyright 2018 by Nelson Education Limited 8
9 Regioselectivity of electrophilic addition is controlled by carbocation stability. Copyright 2018 by Nelson Education Limited 9
10 8.3.3 Markovnikov s rule The major regioisomer product in an electrophilic addition is the one formed from the most stable carbocation. Copyright 2018 by Nelson Education Limited 10
11 8.3.4 Stability of carbocations Electrostatic potential maps for substituted carbocations: less stable more stable Greater degree of substitution results in greater positive charge dissipation (reduced intensity of blue regions) and more effective stabilization. Copyright 2018 by Nelson Education Limited 11
12 8.3.5 Stabilization of carbocations by hyperconjugation Hyperconjugation: electron donation from a s bond Copyright 2018 by Nelson Education Limited 12
13 8.3.6 Stabilization of carbocations by charge delocalization Carbocations are stabilized by electron-donating groups. Copyright 2018 by Nelson Education Limited 13
14 8.3.7 Applying the Hammond postulate Hammond postulate: the structure of a transition state resembles the species nearest to it in free energy Recall: Lower energy transition state faster reaction rate Copyright 2018 by Nelson Education Limited 14
15 Copyright 2018 by Nelson Education Limited 15
16 8.3.8 Reactions with carbocations are not stereoselective Copyright 2018 by Nelson Education Limited 16
17 8.4 Markovnikov Addition of Water to Alkenes Copyright 2018 by Nelson Education Limited 17
18 Copyright 2018 by Nelson Education Limited 18
19 Mechanism: Copyright 2018 by Nelson Education Limited 19
20 Mechanism (continued): (minor) (major) Copyright 2018 by Nelson Education Limited 20
21 Note the similarity in mechanism for addition of HBr vs H 2 O: Copyright 2018 by Nelson Education Limited 21
22 8.4.1 Addition of alcohols by acid catalysis Mechanism is essentially identical to addition of H 2 O. Copyright 2018 by Nelson Education Limited 22
23 8.4.2 Addition of water by oxymercuration-demurcuration Mild reaction conditions Formation of mercurium ion (occurs in a single step): Copyright 2018 by Nelson Education Limited 23
24 Mechanism: more stabilized transition state Copyright 2018 by Nelson Education Limited 24
25 Mechanism (continued): major minor The path that incorporates the more stabilized transition state (red) proceeds more quickly. Copyright 2018 by Nelson Education Limited 25
26 8.5 Carbocation Rearrangements Copyright 2018 by Nelson Education Limited 26
27 s bonds can relocate (shift) to generate more stable carbocation intermediates. Copyright 2018 by Nelson Education Limited 27
28 Shifts in systems stabilized by charge delocalization: Copyright 2018 by Nelson Education Limited 28
29 8.6 Addition of Halogens to Double Bonds Copyright 2018 by Nelson Education Limited 29
30 Charge separation in diatomic halogens: Mechanism (compare with oxymercuration): Copyright 2018 by Nelson Education Limited 30
31 Stereochemistry of halogenation: anti addition product Example: Copyright 2018 by Nelson Education Limited 31
32 8.6.1 Addition of hypohalous acids Mechanism (compare with halogenation and acid-catalyzed hydration): Copyright 2018 by Nelson Education Limited 32
33 Stereochemistry of hypohalous acid addition: Compare with halogenation. Copyright 2018 by Nelson Education Limited 33
34 8.7 Other Types of Electrophilic Additions Copyright 2018 by Nelson Education Limited 34
35 8.7.1 Epoxidation of alkenes mcpba = m-chloroperoxybenzoic acid Copyright 2018 by Nelson Education Limited 35
36 Mechanism: Reactions of epoxides: Copyright 2018 by Nelson Education Limited 36
37 8.7.2 Hydroboration: An anti-markovnikov addition Mechanism: Copyright 2018 by Nelson Education Limited 37
38 Regioselectivity: Stoichiometry: A single borane reagent reacts three times Copyright 2018 by Nelson Education Limited 38
39 Further transformation after hydroboration: Stereochemistry in hydroboration reactions Copyright 2018 by Nelson Education Limited 39
40 8.7.4 Hydrogenation of double bonds Metal catalyst serves as reaction surface: Copyright 2018 by Nelson Education Limited 40
41 8.7.5 Diene reactions Dienes: Electron delocalization: Copyright 2018 by Nelson Education Limited 41
42 8.7.6 Markovnikov addition of electrophiles to dienes Addition to isolated dienes Copyright 2018 by Nelson Education Limited 42
43 Addition to conjugated dienes Copyright 2018 by Nelson Education Limited 43
44 thermodynamic product Copyright 2018 by Nelson Education Limited 44
45 8.7.7 Alkyne reactions Structure of alkyne triple bond: Copyright 2018 by Nelson Education Limited 45
46 8.7.8 Markovnikov addition of electrophiles to alkynes Copyright 2018 by Nelson Education Limited 46
47 Stereoselectivity: Regioselectivity: Copyright 2018 by Nelson Education Limited 47
48 Addition of water: Acid-catalyzed hydration Step 1: Step 2: enol Copyright 2018 by Nelson Education Limited 48
49 Addition of water: Oxymercurartion-demercuration Note enol-ketone tautomerization in the final two steps. Copyright 2018 by Nelson Education Limited 49
50 8.7.9 Anti-Markovnikov additions to alkynes Copyright 2018 by Nelson Education Limited 50
51 Hydrogenation of alkynes Complete hydrogenation: Partial hydrogenation: Copyright 2018 by Nelson Education Limited 51
52 8.8 Patterns in Alkene Addition Reactions Copyright 2018 by Nelson Education Limited 52
53 Mechanistic patterns: Cyclic intermediates Copyright 2018 by Nelson Education Limited 53
54 Mechanistic patterns: Alkenes vs alkynes Copyright 2018 by Nelson Education Limited 54
55 Chapter summary Electron-rich p bonds can serve as nucleophiles in addition reactions with a variety of electrophiles. Regiochemistry of Markovnikov additions is controlled by carbocation stability. Many electrophilic addition reactions involve cyclic intermediates. Anti-Markovnikov addition can be achieved through hydroboration. Alkenes and alkynes react via similar mechanisms. Copyright 2018 by Nelson Education Limited 55
1. Radical Substitution on Alkanes. 2. Radical Substitution with Alkenes. 3. Electrophilic Addition
1. Radical Substitution on Alkanes Only Cl and Br are useful at the laboratory level. Alkane reactivity: tertiary > secondary > primary > methyl Numbers below products give their relative yield. Relative
More information2/26/18. Practice Questions. Practice Questions B F. How many steps are there in this reaction?
Practice Questions Practice Questions D B F C E A G How many steps are there in this reaction? 1 Practice Questions D B F C E A G What is the highest-energy transitions state? Practice Questions D B F
More informationChem 251 Fall Learning Objectives
Learning Objectives Chapter 8 (last semester) 1. Write an electron-pushing mechanism for an SN2 reaction between an alkyl halide and a nucleophile. 2. Describe the rate law and relative rate of reaction
More informationORGANIC - BROWN 8E CH ALKENES AND REACTIONS OF ALKENES
!! www.clutchprep.com CONCEPT: ALKENES and ALKYNES Alkenes/Alkynes are named by adding the suffix modifier (- /- ) to the end of the root. Alkenes/alkynes receive in numbering alkanes Location is assigned
More informationORGANIC - CLUTCH CH ADDITION REACTIONS.
!! www.clutchprep.com CONCEPT: GENERAL MECHANISM Addition reactions are ones in which 1 bond is broken and 2 new bonds are formed. They are the inverse of reactions EXAMPLE: Provide the mechanism for the
More informationChapter 4. Reactions of alkenes. Addition reactions Carbocations Selectivity of reactions
Chapter 4 Reactions of alkenes Addition reactions Carbocations Selectivity of reactions Prob 47 p192. Give the reagents that would be required (including catalyst). Ch 4 #2 Electrophilic addition Ch 4
More informationPreparation of alkenes
Lecture 11 אלקנים הכנה ותגובות של אלקנים: הידרוגנציה, סיפוח הידרוהלוגנים )כלל מארקובניקוב(, סיפוח הלוגנים והסטראוכימיה של תוצרי הסיפוח, הידרובורציה, אפוקסידציה, אוזונוליזה. 1 Preparation of alkenes 1.
More informationREACTION 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
More informationLECTURE #13 Tues., Oct.18, Midterm exam: Tues.Oct.25 during class Ch.1, , 7.10, 2, Sections
CEM 221 section 01 LECTURE #13 Tues., Oct.18, 2005 Midterm exam: Tues.Oct.25 during class Ch.1, 7.2-7.5, 7.10, 2, 3.1-3.5 ASSGNED READNGS: TODAY S CLASS: Sections 4.1 4.6 NEXT CLASS: rest of Ch.4 http://artsandscience.concordia.ca/facstaff/p-r/rogers
More informationDouble and Triple Bonds. The addition of an electrophile and a
Chapter 11 Additions to Carbon-Carbon Double and Triple Bonds The addition of an electrophile and a nucleophile to a C-C C double or triple bonds 11.1 The General Mechanism Pi electrons of the double bond
More informationChapter 8 - Alkenes and Alkynes II Addition Reactions of Alkenes - Electrons in the π bond of alkenes react with electrophiles
Andrew Rosen Chapter 8 - Alkenes and Alkynes II 8.1 - Addition Reactions of Alkenes - Electrons in the π bond of alkenes react with electrophiles 8.2 - Electrophilic Addition of Hydrogen Halides to Alkenes:
More informationChapter 3. Alkenes And Alkynes
Chapter 3 Alkenes And Alkynes Alkenes ydrocarbons containing double bonds C C double bond the functional group center of reactivity Molecular Formula of Alkene Acyclic alkene: C n 2n Cyclic alkene: C n
More informationChapter 8 Alkenes and Alkynes II: Addition Reactions
Chapter 8 Alkenes and Alkynes II: Addition Reactions Introduction: Additions to Alkenes Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds The π electrons of
More informationChapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes
Additions to Alkenes Chapter 8 Alkenes and Alkynes II: Addition Reactions Generally the reaction is exothermic because one p and one s bond are converted to two s bonds Alkenes are electron rich The carbocation
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 informationCHEMISTRY Topic #4: Electrophilic Addition Reactions of Alkenes and Alkynes Fall 2018 Dr. Susan Findlay
EMISTRY 2600 Topic #4: Electrophilic Addition Reactions of Alkenes and Alkynes Fall 2018 Dr. Susan Findlay rganic Reactions (EM 2500 Review) Most reactions in organic chemistry fall into one (or more)
More informationChapter 7. Alkenes: Reactions and Synthesis
Chapter 7. Alkenes: Reactions and Synthesis 1 Synthesis of Alkenes: Elimination Reactions 1. Dehydrohalogenation of alkyl halides. loss of requires CH 2 CH 2 Cl Zaitsev s Rule: CH 2 C 2. Dehydration of
More informationA) I B) II C) III D) IV E) V
Exam Name SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question. 1) Complete the following reaction and provide a detailed, step-by-step mechanism for the process.
More informationChapter 3 Alkenes and Alkynes. Excluded sections 3.15&3.16
Chapter 3 Alkenes and Alkynes Excluded sections 3.15&3.16 3.1 Definition and Classification Alkene: a hydrocarbon that contains one or more carboncarbon double bonds. ethylene is the simplest alkene. Alkyne:
More informationChapter 8 Alkenes and Alkynes II: Addition Reactions "
Chapter 8 Alkenes and Alkynes II: Addition Reactions Additions to Alkenes Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds Alkenes are electron rich The π
More informationLearning 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
More information+ HBr!H = OH CH CH 2. HgOAc
radical substitution Cl hv + Cl 2 + Cl! = Energy radical addition RR + electrophilic addition + C3 C3! = Energy Energy + 2 acetone water + 2 2 +! =! = Energy Energy acid catalyzed hydration + 2 +! = Energy
More informationDienes & Polyenes: An overview and two key reactions (Ch )
Dienes & Polyenes: An overview and two key reactions (h. 14.1-14.5) Polyenes contain more than one double bond and are very common in natural products (ex: carotene). Diene chemistry applies to trienes,
More informationChapter 8: Chemistry of Alkynes (C n H 2n-2 )
hapter 8: hemistry of Alkynes ( n 2n-2 ) Bonding & hybridization Both are sp-hybridized Bond angles = 180 o 1 σ + 2 π bonds Linear around lassification R R R' σ bond energy: 88 kcal/mol π bond energy:
More informationAlso called an olefin but alkene is better General formula C n H 2n (if one alkene present) Can act as weak nucleophiles
Alkenes - Structure, Stability, Nomenclature Also called an olefin but alkene is better General formula C n H 2n (if one alkene present) unsaturated - contain fewer than maximum H's possible per C Can
More information2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene?
Quiz 7.1 Alkene Additions and Hydrohalogenations 1. Which is the most stable carbocation? 2. Which of the following is an intermediate in the Markovnikov addition of HBr to 2- methylcyclohexene? 3. What
More informationChapter 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
More informationWhen H and OH add to the alkyne, an enol is formed, which rearranges to form a carbonyl (C=O) group:
Next Up: Addition of, : The next two reactions are the Markovnikov and non-markovnikov additions of and to an alkyne But you will not see alcohols form in this reaction! When and add to the alkyne, an
More informationHONORS ORGANIC CHEM. HAHS MRS. RICHARDS
NRS RGANIC CEM. AS MRS. RICARDS RGANIC CEMISTRY: FINAL EXAM REVIEW List of Topics: While the exam will specifically focus on material from Quarter 2, an understanding of several important concepts from
More informationChapter 8 Alkenes: Reactions
Chamras Glendale Community College Organic Chemistry 105 Chapter 8 Alkenes: Reactions Name Type 1. alo-hydrogenation (Ionic & Radical) Electrophilic Addition 2. ydration (Acid-Catalyzed) Electrophilic
More informationJust Chemistry Department Organic Chemistry 217
Part 2 Just Chemistry Department Organic Chemistry 217 Chapter 3 Alkenes And Alkynes كيمياء عضوية ك 217 د. حسين المغيض Dr. Hussein Al-Mughaid Direct hydration: Addition of H 2 O (Acid-catalyzed hydration)
More informationChapter 5. Reactions of Alkenes and Alkynes
Chapter 5. Reactions of Alkenes and Alkynes Learning objectives: 1. Identify the followings from a reaction coordinate diagram when applicable: endothermic or exothermic reactions, activation energy, heat
More informationOChem 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
More informationAlkenes - Addition Reactions
Alkenes - Addition Reactions Alkenes- reactions. Addition Ionic Free radical Reduction Oxidation Substitution Reactions, alkenes: 1. Addition of hydrogen (reduction). 2. Addition of halogens. 3. Addition
More informationChapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy
Chapter 15: Conjugated Systems, Orbital Symmetry, and UV Spectroscopy Conjugated unsaturated systems have a p orbital on a carbon adjacent to a double bond The p orbital can come from another double (e.g.
More informationNuggets of Knowledge for Chapter 12 Alkenes (II) Chem reaction what is added to the C=C what kind of molecule results addition of HX HX only
I. Addition Reactions of Alkenes Introduction Nuggets of Knowledge for Chapter 12 Alkenes (II) Chem 2310 An addition reaction always involves changing a double bond to a single bond and adding a new bond
More informationThis reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds.
This reactivity makes alkenes an important class of organic compounds because they can be used to synthesize a wide variety of other compounds. Mechanism for the addition of a hydrogen halide What happens
More informationChapter 19: Alkenes and Alkynes
Chapter 19: Alkenes and Alkynes The vast majority of chemical compounds that we know anything about and that we synthesize in the lab or the industrial plant are organic compounds. The simplest organic
More informationOrganic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008
Organic Chemistry I Lesson Objectives, Lesson Problems, Course Outline Spring 2008 Lesson Date Assignment Lesson Objective Description Lesson Problems 4 14-Jan Chapter 1 Quiz Describe how bond polarity
More informationLoudon Chapter 14 Review: Reactions of Alkynes Jacquie Richardson, CU Boulder Last updated 1/16/2018
An alkyne is any molecule with a triple bond between two carbon atoms. This triple bond consists of one σ bond and two π bonds: the σ bond exists on a straight line between carbon atoms, while one π bond
More informationCH Organic Chemistry I (Katz) Practice Exam #3- Fall 2013
C2710 - rganic Chemistry I (Katz) Practice Exam #3- all 2013 Name: Score: Part I - Choose the best answer and write the letter of your choice in the space provided. (32 pts) 1. f the following, which reaction
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 informationPAPER No. : Paper-9, Organic Chemistry-III (Reaction Mechanism-2) MODULE No. : Module-10, Hydroboration Reaction CHEMISTRY
Subject Chemistry Paper No and Title Module No and Title Module Tag Paper-9, Organic Chemistry-III (Reaction Mechanism-2) Module-10, Hydroboration Reaction CHE_P9_M10 TABLE OF CONTENTS 1. Learning Outcomes
More informationLECTURE #14 Thurs., Oct.20, Midterm exam: Tues.Oct.25 during class Ch.1, , 7.10, 2, Sections
CHEM 221 section 01 LECTURE #14 Thurs., Oct.20, 2005 Midterm exam: Tues.Oct.25 during class Ch.1, 7.2-7.5, 7.10, 2, 3.1-3.5 ASSIGNED READINGS: TODAY S CLASS: NEXT LECTURE: Sections 4.7-4.10 finish Ch.4,
More informationChapter 5. Reactions of Alkenes and Alkynes
Learning objectives: Chapter 5. Reactions of Alkenes and Alkynes 1. Differentiate primary, secondary, and tertiary carbocations, and recognize the order of stability for these carbocations. 2. Identify
More informationAlkynes Nomenclature of Alkynes
Chapter 7 Alkynes Alkynes - hydrocarbons containing a carbon-carbon triple bond (2 bonds) Acyclic alkanes = C n H 2n+2 Alkenes and cyclic alkanes = C n H 2n Alkynes (and cyclic alkenes) = C n H 2n-2 The
More informationsp 2 geometry tetrahedral trigonal planar linear ΔH C-C ΔH C-H % s character pk a 464 KJ/mol 33% 44
hapter 10: Alkynes 10.1 Introduction to Alkynes ~ 111 ~ 122 1.06 Å 180 1.1 Å ~ 116 1.08 Å 1.54 Å 1.34 Å 1.20 Å hybridization of sp 3 sp 2 sp geometry tetrahedral trigonal planar linear 368 KJ/mol 632 KJ/mol
More informationChapter 5B. Functional Group Transformations: The Chemistry. Related Reactions
Chapter 5B Functional Group Transformations: The Chemistry of fcarbon-carbon C b π-bonds B d and Related Reactions Oxymercuation-Demercuration Markovnikov hydration of a double bond 1 Mechanism Comparision
More informationC h a p t e r N i n e: Addition Reactions of Alkenes
C h a p t e r N i n e: Addition Reactions of Alkenes. H C 2 H Biosynthesis of a prostaglandin from arachidonic acid: intermediate intramolecular radical addition CHM 321: Summary of Important Concepts
More informationCHEMISTRY 231 GENERAL ORGANIC CHEMISTRY I FALL 2014 List of Topics / Examination Schedule
Page 1 of 5 CHEMISTRY 231 FALL 2014 List of Topics / Examination Schedule Unit Starts Topic of Study 20 Aug 2014 STRUCTURE AND BONDING Suggested Reading: Chapter 1 29 Aug 2014 ALKANES & CYCLOALKANES Suggested
More informationLecture Notes Chem 51B S. King I. Conjugation
Lecture Notes Chem 51B S. King Chapter 16 Conjugation, Resonance, and Dienes I. Conjugation Conjugation occurs whenever p-orbitals can overlap on three or more adjacent atoms. Conjugated systems are more
More informationOrganic Chemistry, Second Edition. Janice Gorzynski Smith University of Hawai i. Chapter 10 Alkenes
Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai i Chapter 10 Alkenes Prepared by Rabi Ann Musah State University of New York at Albany Copyright The McGraw-Hill Companies,
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 informationCHE1502. Tutorial letter 203/1/2016. General Chemistry 1B. Semester 1. Department of Chemistry
E1502/203/1/2016 Tutorial letter 203/1/2016 General hemistry 1B E1502 Semester 1 Department of hemistry This tutorial letter contains the answers to the questions in assignment 3. FIRST SEMESTER: KEY T
More information6.10 Acid-Catalyzed Hydration of Alkenes. Acid-Catalyzed Hydration of Alkenes
Acid-atalyzed ydration of Alkenes 6.10 Acid-atalyzed ydration of Alkenes O O reaction is acid catalyzed; typical hydration medium is 50% 2 SO 4-50% 2 O Follows Markovnikov's Rule Follows Markovnikov's
More informationThere are several possible arrangements for a molecule which contains two double bonds (diene): 1. Isolated: (two or more single bonds between them)
1 Chapter 15: Conjugation and Reactions of Dienes I. Introduction to Conjugation There are several possible arrangements for a molecule which contains two double bonds (diene): 1. Isolated: (two or more
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I. 5 Credit Hours. Prepared by: Richard A. Pierce
JEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean
More informationNuggets 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
More information5. Reactions of Alkenes (text )
2009, Department of hemistry, The University of Western Ontario 5.1 5. Reactions of Alkenes (text 5.1 5.5) A. Addition Reactions In hapter 4, we saw that π bonds have electron density on two sides of the
More informationOChem 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
More informationCHAPTER 9 THEORY OF RESONANCE BY, G.DEEPA
CHAPTER 9 THEORY OF RESONANCE BY, G.DEEPA Conjugation in Alkadienes and Allylic Systems conjugation a series of overlapping p orbitals The Allyl Group allylic position is the next to a double bond 1 allyl
More informationDetailed Course Content
Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum
More informationChapter 8 Alkenes and Alkynes II: Addition Reactions. Alkenes are electron rich. Additions to Alkenes
Additions to Alkenes hapter 8 Alkenes and Alkynes II: Addition eactions Generally the reaction is exothermic because one π and one σ bond are converted to two σ bonds Alkenes are electron rich The carbocation
More informationChapter 8 Reactions of Alkenes
Chapter 8 Reactions of Alkenes Electrophilic Additions o Regio vs stereoselectivity Regio where do the pieces add? Markovnikov s rule hydrogen will go to the side of the double bond with most hydrogens.
More information2. Hydrohalogenation: Propylene reacts with HBr to form 2-bromopropane.
Objective 12. Apply reactivity principles to Electrophilic Addition reactions 1: alkenes identify structural features (pi bond) and electrophiles, use curved arrows to predict product. Structural features:
More informationAugust 10, Prospective Chemistry 5511 Students. SUBJECT: Course Syllabus for Chemistry 5511 Fall 2011
TO: FROM: Prospective Chemistry 5511 Students Peter Gaspar August 10, 2011 SUBJECT: Course Syllabus for Chemistry 5511 Fall 2011 Chemistry 5511 Mechanistic Organic Chemistry is the first semester of a
More informationCOURSE UNIT DESCRIPTION. Type of the course unit. Mode of delivery Period of delivery Language of instruction Face to face Autumn English
Course unit title Organic Chemistry I Lecturer(s) Dr. Rimantas Vaitkus COURSE UNIT DESCRIPTION Department Dept. Organic Chemistry, Vilnius University Cycle First Type of the course unit Mode of delivery
More informationORGANIC - BROWN 8E CH ALDEHYDES AND KETONES.
!! www.clutchprep.com CONCEPT: ALDEHYDE NOMENCLATURE Replace the suffix of the alkane -e with the suffix On the parent chain, the carbonyl is always terminal, and receive a location As substituents, they
More information11/5/ Conjugated Dienes. Conjugated Dienes. Conjugated Dienes. Heats of Hydrogenation
8.12 Sites of unsaturation Many compounds have numerous sites of unsaturation If sites are well separated in molecule they react independently If sites are close together they may interact with one another
More informationOrganic 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
More informationCHEM2410 Organic Chemistry I - Honors
CHEM2410 Organic Chemistry I - Honors The University of Toledo Department of Chemistry and Biochemistry College of Natural Sciences and Mathematics CRN: 49264/49268 (Sect. 091/092) Instructor: Dr. Peter
More informationLecture 3: Aldehydes and ketones
Lecture 3: Aldehydes and ketones I want to start by talking about the mechanism of hydroboration/ oxidation, which is a way to get alcohols from alkenes. This gives the anti-markovnikov product, primarily
More informationAcid-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.
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 4-3: Continue Alkynes: An Introduction to Organic Synthesis Based on: McMurry s Organic Chemistry,
More informationLECTURE #06 Thurs., Feb.07, 2008
CEM 221 section 52 LECTURE #06 Thurs., Feb.07, 2008 ASSIGNED READINGS: TODAY S CLASS: 3.6-3.8 Introduction to organic rxn mechanisms 4.1-4.5 Alkene reactions electrophilic addition mechanism carbocation
More informationLecture 11 Organic Chemistry 1
EM 232 rganic hemistry I at hicago Lecture 11 rganic hemistry 1 Professor Duncan Wardrop February 16, 2010 1 Self Test Question What is the product(s) of the following reaction? 3 K( 3 ) 3 A 3 ( 3 ) 3
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 informationBasic 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
More informationOrganic Chemistry. Alkenes
Organic Chemistry by Nurlin Abu Samah, Dr. Md. Shaheen & Dr. Nadeem Akhtar Faculty of Industrial Sciences & Technology nurlin@ump.edu.my Chapter Description Aims The students should understand the fundamental
More information10: Alkenes and Alkynes. Electrophilic and Concerted Addition Reactions
10: Alkenes and Alkynes. Electrophilic and Concerted Addition Reactions Addition Reactions Electrophilic Addition of H-X or X2 to Alkenes Addition of H-X and X2 to Alkynes Alkenes to Alcohols by Electrophilic
More informationAlcohol Synthesis. Dr. Sapna Gupta
Alcohol Synthesis Dr. Sapna Gupta Synthesis of Alcohols Alcohols can be synthesized from several functional groups. Nucleophilic substitution of O - on alkyl halide ydration of alkenes water in acid solution
More informationChapter 8. Alkenes and Alkynes II: Addition Reactions. Ch. 8-1
hapter 8 Alkenes and Alkynes II: Addition Reactions h. 8-1 1. Addition Reactions of Alkenes E + E Nu Nu h. 8-2 1A. ow To Understand Additions to Alkenes This is an addition reaction: E Nu added across
More informationp 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
More informationCHEMISTRY Topic #3: Addition Reactions of Conjugated Dienes Spring 2017 Dr. Susan Findlay
CEMISTRY 2600 Topic #3: Addition Reactions of Conjugated Dienes Spring 2017 Dr. Susan Findlay Different Kinds of Dienes When a molecule contains multiple π-bonds, their reactivity is dictated in part by
More informationThis syllabus is printed on both sides of each page in the hard-copy version.
TO: FROM: Prospective Chemistry 5511 Students Peter Gaspar August 13, 2010 SUBJECT: Course Syllabus for Chemistry 5511 Fall 2010 Chemistry 5511 Mechanistic Organic Chemistry is the first semester of a
More informationLearning Guide for Chapter 12 - Alkenes (II)
Learning Guide for Chapter 12 - Alkenes (II) I. Addition reactions of alkenes Introduction to addition reactions Catalytic hydrogenation of alkenes Hydroxylation of alkenes Epoxidation of alkenes Cyclopropanation
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 informationOrganic Chemistry I: Reactions and Overview
Organic Chemistry I: Reactions and Overview Andrew Rosen Editor: Raghav Malik January 13, 2013 Contents I Library of Synthetic Reactions 3 II Organic Trends and Essentials 4 1 The Basics: Bonding and Molecular
More informationEther, NaOH. This is a two-step process, but is most commonly done as a one-pot procedure (upper right).
CAPTE 8. ALKENES: EACTINS AND SYNTESIS ydration of Alkenes by xymercuration-eduction - concerted formation of three-membered ring intermediate - addition of water occurs through anti stereoselectivity
More informationAlkenes. Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula C n H 2n. Nomenclature
Alkenes Alkenes-hydrocarbons with a carbon-carbon double bond. Alkenes have the formula n 2n. Nomenclature Alkenes are named in the same manner as alkanes with the following adjustments. 1. Find the longest
More informationORGANIC - EGE 5E CH. 7 - NUCLEOPHILIC SUBSTITUTION AND ELIMINATION REACTIONS
!! www.clutchprep.com CONCEPT: INTRODUCTION TO SUBSTITUTION Previously, we discussed the various ways that acids could react with bases: Recall that in these mechanisms, electrons always travel from density
More informationAlkenescontain a C=C double bond (also occasionally called olefins). Alkenes are very common in natural and synthetic organic compounds.
Chapter 6: Alkenes: structure and reactivity Alkenescontain a C=C double bond (also occasionally called olefins). Alkenes are very common in natural and synthetic organic compounds. 6.2 Degree of unsaturation
More informationChemistry 233 Exam 3 (Green) The Periodic Table
Name: Last First MI Chemistry Exam (Green) Summer 7 Dr. J. sbourn Instructions: The first questions of this exam should be answered on the provided Scantron. You must use a pencil for filling in the Scantron
More informationConjugated Systems, Orbital Symmetry and UV Spectroscopy
Conjugated Systems, Orbital Symmetry and UV Spectroscopy Introduction There are several possible arrangements for a molecule which contains two double bonds (diene): Isolated: (two or more single bonds
More informationJEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I. 5 Credit Hours. Prepared by: Richard A. Pierce. Revised by: Sean Birke October, 2013
JEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I 5 Credit Hours Prepared by: Richard A. Pierce Revised by: Sean Birke October, 2013 Ms. Linda Abernathy, Math, Science & Business Division Chair
More informationS N 1 Displacement Reactions
S N 1 Displacement Reactions Tertiary alkyl halides cannot undergo S N 2 reactions because of the severe steric hindrance blocking a backside approach of the nucleophile. They can, however, react via an
More information1. Addition of HBr to alkenes
eactions of Alkenes I eading: Wade chapter 8, sections 8-1- 8-8 tudy Problems: 8-47, 8-48, 8-55, 8-66, 8-67, 8-70 Key Concepts and kills: Predict the products of additions to alkenes, including regiochemistry
More informationMore Tutorial at
1. MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question (50 pts). 1) Which of the following statements about propene, CH3CH CH2, is 1) correct? A) There
More informationLearning Guide for Chapter 17 - Dienes
Learning Guide for Chapter 17 - Dienes I. Isolated, conjugated, and cumulated dienes II. Reactions involving allylic cations or radicals III. Diels-Alder Reactions IV. Aromaticity I. Isolated, Conjugated,
More informationWhat is the major product of the following reaction?
What is the major product of the following reaction? Predict the major product of the following reaction: 2-methylbutane + Br 2 /light energy? A) 1-bromo-2-methylbutane B) 2-bromo-2-methylbutane C) 2-bromo-3-methylbutane
More information