Chapter 8 Alkenes: Reactions
|
|
- Paula Waters
- 6 years ago
- Views:
Transcription
1 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 Addition 3. Oxymercuration-Demercuration Electrophilic Addition 4. Alkoxymercuration-Demercuration Electrophilic Addition 5. ydroboration-oxidation Electrophilic Addition 6. ydrogenation Catalytic Addition 7. Cyclopropanation Carbene Addition 8. alogenation Oxidative Addition 9. Vicinal alohydrin Formation Oxidative Addition 10. Epoxidation Oxidative Addition 11. Anti ydroxylation Oxidative Addition 12. Syn ydroxylation Oxidative Addition 13. Oxidative Cleavage by Ozonolysis Oxidative Cleavage 14. Oxidative Cleavage by Potassium Permanganate Oxidative Cleavage The Common Theme in Addition Reactions of Alkenes First step: The C=C π-bond act as a source of available electrons, attacks electron-deficient species. Y X 1
2 ydro-alogenation Reaction (Addition of hydrogen halides) + X X Rearrangement? Variety of solvents are used: C 6 6, C 5 12, C 3 COO, CCl 3, etc Reactivity of alides: The Reason: F << Cl < Br < I Regiochemistry of addition: (Reaction is Regioselective) 2
3 Example: Br + Br Acetic Acid Mechanism: Br + Br intermediate Regioselectivity of the first addition Facial selectivity of the second addition Markovnikov s Rule: 3
4 Markovnikov Addition vs. Anti-Markovnikov Addition: Example: Write the mechanism & predict the product: (Possibility for rearrangement?) + Cl 4
5 ***Special Case for ydro-alogenation of Alkenes*** In Presence of PEROXIDES, when the alkene is hydrobrominated, the reaction yields the opposite regiochemical outcome: Example: + Br 3 C O O C 3 Br Mechanism: Regiochemistry of hydrohalogenation reactions of alkenes: (Reaction is Regioselective) 5
6 ydration (Acid-Catalyzed) O O DILUTE (50%) sulfuric acid is required for this reaction. Rearrangement? Regiochemistry of addition: (Reaction is Regioselective) Mechanistic Example: + 2 O + 6
7 ydration by Oxymercuration-Demercuration g(oac) 2 (aq) O goac NaB 4 O Rearrangement? Regiochemistry of addition: (Reaction is Regioselective) 7
8 Mechanistic Example: 8
9 Alkoxymercuration-Demercuration g(oac) 2 RO RO goac NaB 4 RO Rearrangement? Regiochemistry of addition: (Reaction is Regioselective) Mechanistic Example: 9
10 ydroboration-oxidation R B 3. TF R 3 B R 3 R 2 O 2 O 3 R O Rearrangement Regiochemistry of addition: (Reaction is Regioselective) Stereochemistry of addition: (Reaction is stereospecific) Mechanistic Example: 1. ydroboration: 10
11 Stereochemistry of ydroboration: (A relevant issue for cyclic alkenes) 2. Oxidation: Exercise: Propose reaction conditions that would achieve the following transformations: O O 11
12 ydrogenation R 1 R 3 R 1 R 3 2, Cat. R 2 R 4 R 2 R 4 General Remarks: Two C- Bonds are formed. (Very Strong) Very exothermic: Δ rxn < 0 Catalysts: Pd, Pt, Rh, or Ni: all Solid metals (heterogeneous catalysis) Stereochemistry of addition: Syn Addition: Addition of both s takes place on TE SAME FACE of the double bond. (Reaction is Stereospecific) C C Reaction happens in one step. Catalyst 12
13 Cyclopropanation (AKA: Simmons-Smith Reaction) Addition Type: Carbene Addition + C Problems with direct use of carbenes: 1. Diazomethane is VERY EXPLOSIVE 2. Diazomethane is VERY TOXIC 3. UNDESIRED SIDE PRODUCTS usually result Simmons-Smith Reaction utilizes a CARBENOID to achieve the same transformation. Simmons-Smith reagent: C 2 I 2 C 2 I 2 Zn, CuCl Example: 13
14 alogenation X 2 + X X Reaction is stepwise Rearrangement: Stereochemistry of addition: (Reaction is Stereospecific) Intermediate: Mechanistic Example: 14
15 alogenation of asymmetric alkenes: Br 2 Br 2 15
16 Stereochemistry of alogenation: Br 2 Br 2 16
17 Vicinal alohydrin Formation + X 2 2 O X + O + X Reaction is stepwise Rearrangement Stereochemistry of addition: (Reaction is Stereospecific) Regiochemistry of Addition: (Reaction is Regioselective) Intermediate: Mechanistic Example: 17
18 Epoxidation O O O + + R O O R O Mechanism: Rearrangement: Stereochemistry of addition: (Reaction is Stereospecific) Mechanistic Example: MCPBA: 18
19 Anti ydroxylation Acid-Catalyzed Epoxide Ring Opening O 3 O + O O Mechanism: Rearrangement: Stereochemistry of addition: (Reaction is Stereospecific) Mechanistic Example: In case of asymmetric alkenes: MCPBA C 2 Cl 2 19
20 Syn ydroxylation 1. KMnO 4 2. O (aq) OR 1. OsO O 2 O O Rearrangement: Stereochemistry of addition: (Reaction is Stereospecific) Mechanistic Example: 20
21 Oxidative Cleavage by Ozonolysis R 1 R 3 2. Zn, 2 O R 1 R O 3, C 2 Cl 2 OR O + O R 2 R 4 2. (C 3 ) 2 S R 2 R 4 Reaction is stepwise Oxidative Cleavage by Potassium Permanganate R 1 R 3 R 1 + KMnO 4 (Conc.) O + O R 3 R 2 eat R 2 O 21
Electrophilic Addition
. Reactivity of = Electrons in pi bond are loosely held. Electrophiles are attracted to the pi electrons. arbocation intermediate forms. Nucleophile adds to the carbocation. Net result is addition to the
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 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 informationChapter 7: Alkene reactions conversion to new functional groups
hapter 7: Alkene reactions conversion to new functional groups Preparation of alkenes: two common elimination reactions 1. Dehydration of alcohols Dehydration is a common biochemical reaction in carbohydrate
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 informationReactivity of C=C. Chapter 8 Reactions of Alkenes. Types of Additions. Electrophilic Addition. Addition of HX (1) Addition of HX (2)
rganic hemistry, 5 th Edition L. G. Wade, Jr. hapter 8 Reactions of Alkenes Jo Blackburn Richland ollege, allas, TX allas ounty ommunity ollege istrict 2003, Prentice all Reactivity of = Electrons in pi
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 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 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 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 informationChapter 7: Alkenes: Reactions and Synthesis
hapter 7: Alkenes: Reactions and Synthesis alcohol alkane halohydrin 1,2-diol 1,2-dihalide carbonyl halide halide Addition Y Y Elimination Electrophilic Addition Dehydrohalogenation: loss of from an alkyl
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 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 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 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: Addition Reactions
Chapter 8: Addition Reactions Addition Reactions to Alkenes (Section 8.1) Markovnikov s Rule (Section 8.2) Stereochemistry of Ionic Addition to Alkenes (Section 8.3) 2 S 4 Additions to Alkenes (Section
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 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 informationORGANIC CHEMISTRY- 1
ORGANIC CEMISTRY- 1 ALKENES Alkenes are also called Olefins (C n 2n ) unsaturated hydrocarbons. Alkenes occur abundantly in nature. Ethylene ( 2 C=C 2 ) is a plant hormone that induces ripening in fruit.
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 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 informationalkene: versatile function group
alkene: versatile function group X Alcohol Alkane alohydrin 1,2-Diol X X C C Carbonyl compound 1,2-Dihalide X C Cyclopropane alide Epoxide 7.1 Preparation of Alkenes: A Review of Elimination Reactions
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 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 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 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 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 informationp Bonds as Nucleophiles
Chapter 8 p Bonds as Nucleophiles REACTIONS OF ALKENES, ALKYNES, DIENES, AND ENOLS Copyright 2018 by Nelson Education Limited 1 8.2.1 Orbital structure of alkenes Geometry: Electrostatic potential: Electron-rich
More informationAlkenes are prepared by the reverse of the electrophilic reactions in the last chapter. That is, they are prepared by elimination reactions.
Ch 8 Alkene Reactions and Syntheses Alkenes are prepared by the reverse of the electrophilic reactions in the last chapter. That is, they are prepared by elimination reactions. Dehydrohalogenation - Mechanism
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 information1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors
1.13 Acid-Base Reactions: Lone-Pair Donors & Acceptors I, Cl, N 3, 3 P 4 pka 10 to 5 Super strong acids 3 + pka 1.7 RC 2 pka ~ 5 acids Ph pka ~ 10 get 2, R pka ~ 16 weaker RCC (alkynes) pka ~ 26 RN 2 pka
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 information1. 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 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 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 information1. Addition Reactions of Alkenes
hapter 8 Alkenes and Alkynes II: Addition eactions reated by Professor William Tam & Dr. illis hang h. 8-1 About The Authors These PowerPoint Lecture Slides were created and prepared by Professor William
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 informationEthers. Chapter 14: Ethers, Epoxides, & Sulfides. General Formula: Types: a) Symmetrical: Examples: b) Unsymmetrical: Examples: Physical Properties:
Chamras Chemistry 106 Lecture Notes Examination 1 Materials Chapter 14: Ethers, Epoxides, & Sulfides Ethers General Formula: Types: a) Symmetrical: Examples: b) Unsymmetrical: Examples: Physical Properties:
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 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 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 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 informationOption II: Chiral + Achiral = Optically Active Diastereomers
Option II: Chiral + Achiral = Optically Active Diastereomers What about additions to chiral alkenes? The previous examples were reactions done on achiral alkenes. What is the difference when an alkene
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 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 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 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 informationPart C- section 1 p-bonds as nucleophiles
Part C- section 1 p-bonds as nucleophiles Chemistry of Alkenes (Ch 8, 9, 10) - the double bond prevents free rotation - isomerism cis and trans - nomenclature E and Z (3 or 4 different substituents around
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 informationELECTROPHILIC ADDITIONS OF ALKENES AS THE COUNTERPART OF ELIMINATIONS
ELECTRPHILIC ADDITINS F ALKENES AS THE CUNTERPART F ELIMINATINS INTRDUCTIN - Chapter 8 is mostly about alkene reactions. That is, how one can transform alkenes into other functional groups. Most of these
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 informationIntroduction & Definitions Catalytic Hydrogenations Dissolving Metal Reduction Reduction by Addition of H- and H+ Oxidation of Alcohols Oxidation of
CEM 241- UNIT 4 xidation/reduction Reactions Redox chemistry 1 utline Introduction & Definitions Catalytic ydrogenations Dissolving Metal Reduction Reduction by Addition of - and + xidation of Alcohols
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 informationCHEMISTRY Topic #8: Oxidation and Reduction Reactions Fall 2018 Dr. Susan Findlay
CEMISTRY 2600 Topic #8: xidation and Reduction Reactions Fall 2018 Dr. Susan Findlay xidation States of Carbon Carbon can have any oxidation state from -4 (C 4 ) to +4 (C 2 ). As a general rule, increasing
More informationChapter 8 Addition Reactions to Alkenes
. 8 hapter 8 Addition eactions to Alkenes In this chapter will we study the addition reactions of alkenes. We will see that the π electrons of the double bond are loosely held and that their maximum electron
More informationChemistry 210 Organic Chemistry I Winter Semester 2002 Dr. Rainer Glaser
hemistry 210 Organic hemistry I Winter Semester 2002 Dr. Rainer Glaser Examination #6 Reactions of Alkenes & Alkyne hemistry. Friday, March 26, 2002, 9 9:50 am Name: Question 1. alogenation Reactions.
More informationSynthesis and Retrosynthesis
Synthesis and Retrosynthesis Putting Reactions Together A large part of ganic chemistry involves building me complex molecules from smaller ones using a designed sequence of reactions, i.e. chemical synthesis.
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 informationnsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes
240 Chem nsaturated Hydrocarbons: Alkenes, Cycloalkenes and Dienes 1 Chapter 3 Alkenes or Olefines Crabon-Carbon double bond C n H 2n Hybridization in Alkenes: 1.34 A 2 Nomenclature of Alkenes and Cycloalkenes
More informationthere general method to synthesize alkenes a. acidic conditions acid catalyzed dehydration of alcohols to alkene H H H H H OH 2 H H + H 2 O H H
there general method to synthesize alkenes a. acidic conditions acid catalyzed dehydration of alcohols to alkene O 2 SO 4 heat O 2 SO 4 heat O 2 O 2 2 SO 4 heat + SO 4 + 2 O + SO 4 + 2 O + 2 SO 4 limitation;
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 informationLecture 20 Organic Chemistry 1
CEM 232 rganic Chemistry I at Chicago Lecture 20 rganic Chemistry 1 Professor Duncan Wardrop March 18, 2010 1 Self-Test Question Capnellene (4) is a marine natural product that was isolated from coral
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 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 informationChemistry 210 Organic Chemistry I Winter Semester 2001 Dr. Rainer Glaser
hemistry 210 rganic hemistry I Winter Semester 2001 Dr. Rainer Glaser Examination #3 Alkenes and Alkynes. Structure, Synthesis and Reactions. Friday, April 20, 2001, 9:00-9:50 Name: Answer Key Question
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 informationAlkenes: Reactions and Synthesis
7 Alkenes: Reactions and Synthesis آلکن ها: واکنش ها و سنتز Dr Morteza Mehrdad University of Guilan, Department of Chemistry, Rasht, Iran m-mehrdad@guilan.ac.ir Based on McMurry s Organic Chemistry, 7
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 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 informationChemistry 210 Organic Chemistry I Winter Semester 2002 Dr. Rainer Glaser
hemistry 210 rganic hemistry I Winter Semester 2002 Dr. Rainer Glaser Examination #6 Reactions of Alkenes & Alkyne hemistry. Friday, March 26, 2002, 9 9:50 am Name: Answer Key Question 1. alogenation Reactions.
More informationN.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. Reverse process of dehydration of an alcohol
An Introduction to Organic hemistry N.b. A catalyst is a species which speeds up a chemical reaction but which remains chemically unchanged. ydration (Addition) Reverse process of dehydration of an alcohol
More informationCHEM 203. Topics Discussed on Oct. 16
EM 203 Topics Discussed on Oct. 16 ydrogenation (= saturation) of olefins in the presence of finely divided transition metal catalysts (Ni, Pd, Pt, Rh, Ru...): generic alkene R 1 finely divided Pd (or
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 informationVision. Cis-trans isomerism is key to vision. How rods work H 3 C CH 3. Protein opsin. 11-cis-retinal. Opsin. Rhodopsin.
Vision Cis-trans isomerism is key to vision. 3 C 11 12 3 C C 3 3 C O C 3 11-cis-retinal Protein opsin 3 C 11 12 3 C C 3 3 C N Opsin C 3 Rhodopsin Light photons 3 C N Opsin 3 C 11 12 3 C C 3 C 3 ow rods
More informationChemistry 210 Organic Chemistry I Summer Semester 1999 Dr. Somnath Sarkar
Chemistry 210 Organic Chemistry I Summer Semester 1999 Dr. Somnath Sarkar Examination #3 Elimination Reactions Structure, Synthesis and Reactions of Alkenes and alkynes. Friday, July 23, 1999, 8:40 9:40
More information+ HBr ΔH = OH CH CH 2. HgOAc
radical substitution l hv + l 2 + l Energy radical addition RR + electrophilic addition + 3 3 Energy Energy + 2 acetone water + 2 2 + Energy Energy acid catalyzed hydration + 2 + Energy + + 2 + + 2 = 2
More informationChapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of H X 2. Addition of H OH and addition of Y X 3. Addition to allene and
Chapter 4 Electrophilic Addition to Carbon Carbon Multiple Bonds 1. Addition of X 2. Addition of and addition of Y X 3. Addition to allene and alkyne 4. Substitution at α-carbon 5. eactions via organoborane
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 informationTopic 2 Alkenes and alkynes
Topic 2 Alkenes and alkynes lassification of rganic Reactions Four basic types of organic reaction Acid base reactions Substitution reactions Addition elimination reactions xidation reduction reactions
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 informationCHEM Lecture 7
CEM 494 Special Topics in Chemistry Illinois at Chicago CEM 494 - Lecture 7 Prof. Duncan Wardrop ctober 22, 2012 CEM 494 Special Topics in Chemistry Illinois at Chicago Preparation of Alkenes Elimination
More informationChapter 7. dehydration
hapter 7 7.1 ne problem with elimination reactions is that mixtures of products are often formed. For example, treatment of 2-bromo-2-methylbutane with K in ethanol yields a mixture of two alkene products.
More information10.1. Electrophilic Addition of to to give. Works with HCl HBr HI. Electrophilic Addition Mechanism. H Cl Cl. 3D picture of intermediate: Rxn Coord
10.1 Electrophilic Addition of to to give Works with I F Electrophilic Addition Mechanism 3D picture of intermediate: E xn oord Thermodynamics: + Δ (kcal/mol) + + = Alkene ydration: Electrophilic Addition
More informationLearning Guide for Chapter 15 - Alcohols (II)
Learning Guide for Chapter 15 - Alcohols (II) I. Introduction to alcohol reactivity II. Reactions of alcohols with acids III. Reactions of alcohols with electrophiles alogenated phosphorus and sulfur compounds
More informationChem Lecture 23 Page- 1 -
Chem 230-001 Lecture 23 Page- 1 - ydroboration/ oxidation - acemic trans-2-methylcyclohexanol may be neatly synthesized from 1-methyl- 1-cyclohexene by using a reagent called borane, 3. 0.33 equivs. 3,
More informationCHEM 251 (4 credits): Description
CHEM 251 (4 credits): Intermediate Reactions of Nucleophiles and Electrophiles (Reactivity 2) Description: An understanding of chemical reactivity, initiated in Reactivity 1, is further developed based
More informationAlkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry
Alkenes (Olefins) Chapters 7 & 8 Organic Chemistry, 8 th Edition John McMurry 1 Structure and Bonding 2 Structure and Bonding Rotation around the C=C bond is restricted 90 rotation The p orbitals are orthogonal
More informationCHAPTER 12 HW: REDOX REACTIONS
CAPTER 12 W: REDX REACTINS XIDATIN STATES AND GENERAL CNCEPTS 1. Are the following statements true or false? When a carbon atom changes its oxidation state from -2 to 0 it is reduce The oxidation state
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 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 9 Alkynes. Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Chapter 9 Alkynes Copyright The McGraw-Hill Companies, Inc. Permission required for reproduction or display. 9.1 Sources of Alkynes Acetylene Industrial preparation of acetylene is by dehydrogenation of
More informationHOMEWORK PROBLEMS: ALKYNES. 1. Provide the complete IUPAC name for the following compounds:
CEM 31 MEWRK PRBLEMS: ALKYNES 1. Provide the complete IUPAC name for the following compounds: 2. When the compound below is treated with one equivalent of B 3, where does it react Explain. Where would
More informationChapter 13: Alcohols and Phenols
Chapter 13: Alcohols and Phenols [ Chapter 9 Sections: 9.10; Chapter 13 Sections: 13.1-13.3, 13.9-13.10] 1. Nomenclature of Alcohols simple alcohols C3 C3C2 Eddie Sachs 1927-1964 larger alcohols find the
More informationChem 350 Jasperse Ch. 8 Notes 1
hem 350 Jasperse h. 8 Notes 1 Summary of Alkene Reactions, h. 8. Memorize Reaction, rientation where Appropriate, Stereochemistry where Appropriate, and Mechanism where Appropriate. -all are drawn using
More information1. Which of the following compounds is the weakest base?
I. Multiple-choice Questions Fall 2018 1. Which of the following compounds is the weakest base? a. C3C2 b. C3C2 c. N3 d. C3 e. N2 2. Which of the following functional groups is indicated by a strong and
More informationCh 18 Ethers and Epoxides
Ch 18 Ethers and Epoxides Ethers (R-O-R ) are compounds with two organic groups attached to an sp 3 oxygen. Epoxides are cyclic ethers where the sp 3 O is a part of a 3-membered ring. Thiols (R-S-H ) and
More informationChapter 9 Alkynes. Introduction
hapter 9 Alkynes Introduction Alkynes contain a triple bond. General formula is n 2n-2. Two elements of unsaturation for each triple bond. MST reactions are like alkenes: addition and oxidation. Some reactions
More informationCHEM 263 Oct 25, stronger base stronger acid weaker acid weaker base
CEM 263 ct 25, 2016 Reactions and Synthesis (Preparation) of R- Breaking the - Bond of R- with Metals R + Li 0 or Na 0 or K 0 metal R Li + 1/2 2 alkoxide Breaking the - Bond of R- by Acid-Base Reaction
More informationChapters Additions across C=C π Bonds.
Grossman, CE 230 Chapters 9 10. Additions across C=C π Bonds. We ve learned a number of different substitution and elimination reactions of alkyl halides. We ve learned that compounds with lone pairs are
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 information