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© Prentice Hall 2001Chapter 51 Hydrogen Halide Addition The addition of a hydrogen halide to an alkyne follows Markovnikov’s rule because a secondary vinylic cation is more stable than a primary vinylic cation
© Prentice Hall 2001Chapter 52 Hydrogen Halide Addition When excess hydrogen halide is present, a second equivalent is added Markovnikov’s Rule also is followed for the second addition, forming a geminal dihalide
© Prentice Hall 2001Chapter 53 Hydrogen Halide Addition in the presence of Peroxide Hydrogen peroxide has same effect on hydrogen bromide addition to an alkyne as to an alkene
© Prentice Hall 2001Chapter 54 Halogen Addition to Alkynes Halogens add to alkynes as well as to alkenes Excess halogen leads to the addition of a second equivalent
© Prentice Hall 2001Chapter 55 Addition of Water to Alkynes Water adds to alkynes in the presence of acid to yield an enol
© Prentice Hall 2001Chapter 56 Addition of Water to Alkynes However the initially formed enol reacts further to produce a ketone Such isomers, differing only in the placement of a hydrogen atom, are called tautomers
© Prentice Hall 2001Chapter 57 Mercuric-Ion-Catalyzed Addition of Water to Alkynes
© Prentice Hall 2001Chapter 58 Hydroboration–Oxidation Hydroboration of an internal alkyne leads to a ketone
© Prentice Hall 2001Chapter 59 Addition of Water to an Alkyne
© Prentice Hall 2001Chapter 510 Addition of Hydrogen to an Alkyne
© Prentice Hall 2001Chapter 511 Addition of Hydrogen to an Alkyne
© Prentice Hall 2001Chapter 512 Acidity of a Hydrogen Bonded to an sp Carbon The acidities of hydrocarbons can be compared with the acidities of compounds having hydrogen attached to other second-row elements
© Prentice Hall 2001Chapter 513 Acidity of a Hydrogen Bonded to an sp Carbon The conjugate bases have the following relative base strength because the stronger the acid, the weaker the conjugate base
© Prentice Hall 2001Chapter 514 Acidity of a Hydrogen Bonded to an sp Carbon Relative electronegativities of carbon sp > sp 2 > sp 3 The amide ion is strong enough to remove the proton from an sp carbon
© Prentice Hall 2001Chapter 515 Acidity of a Hydrogen Bonded to an sp Carbon Hydroxide ion is too weak to remove a proton from an sp carbon
© Prentice Hall 2001Chapter 516 Syntheses Using Acetylide Ions Alkylation reactions work best with primary alkyl halides and methyl halides
© Prentice Hall 2001Chapter 517 Starting with 1-butyne, how would you prepare the following ketone? At this point the only way we know to form a ketone is to add water to an alkyne in the presence of a catalyst Introduction to Multistep Synthesis
© Prentice Hall 2001Chapter 518 If the alkyne used has identical substituents on both sp carbons, only one ketone will result 3-Hexyne can be obtained from the starting material by removing the hydrogen bonded to the sp carbon and reacting with an alkyl halide Introduction to Multistep Synthesis
© Prentice Hall 2001Chapter 519 Introduction to Multistep Synthesis Overall we have a two-step synthesis
© Prentice Hall 2001Chapter 520 In designing a synthesis it is best to start from the product and work backwards as we did in this example Introduction to Multistep Synthesis
© Prentice Hall 2001Chapter 521 The thought process is known as retrosynthetic analysis and is indicated by using open arrows Introduction to Multistep Synthesis
Chapter 61 Reactions of Alkynes. Introduction to Multistep Synthesis Chapter 6.
Chapter 51 Reactions of Alkenes and Alkynes. Chapter 5.
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 6 Reactions of Alkynes Introduction to Multistep Synthesis Irene Lee Case Western Reserve.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 6 The Reactions of Alkynes An Introduction to Multistep.
© Prentice Hall 2001Chapter 51 General Formulas The General Formula for an acyclic alkyne is C n H 2n-2 The Simplest Alkyne is HC CH, which has the common.
Puan Rozaini Abdullah School of Bioprocess Engineering.
1 Alkynes Alkynes contain a carbon—carbon triple bond. Terminal alkynes have the triple bond at the end of the carbon chain so that a hydrogen atom is.
Khadijah Hanim bt Abdul Rahman School of Bioprocess Engineering, UniMAP Week 6:20/10/2011 ALKYNES Sem 1: 2011/2012.
ACETYLIDE IONS AND ALKYLATION REACTIONS (REVIEW) SYNTHESIS Dr. Clower CHEM 2412 Fall 2014 McMurry (8 th ed.) sections , 8.1, 9.2, 9.9.
Alkynes. Alkynes: l Are hydrocarbons that contain carbon-carbon triple bonds. l Are also known as acetylenes. l Have the general structural formula C.
Chapter 8: Alkynes Alkynes: An Introduction to Organic Synthesis.
John E. McMurry Paul D. Adams University of Arkansas Lecture 11 (Chapter 9) Alkyne Reactions.
Alkynes. Hydrocarbons with a carbon–carbon triple bond are alkynes. Noncyclic alkynes have the molecular formula C n H 2n-2. Acetylene (HC≡ CH) is the.
Rozaini Abdullah School of Bioprocess Engineering UniMAP Week 5.
ALKENE AND ALKYNE REACTIONS, CONTINUED Dr. Clower CHEM 2411 Spring 2014 McMurry (8 th ed.) sections , , , , 8.10, 8.12,
Chapter 5 Reactions of Alkenes and Alkynes (Part II) Essential Organic Chemistry Paula Yurkanis Bruice.
Alkynes Alkynes contain a carbon—carbon triple bond. Terminal alkynes have the triple bond at the end of the carbon chain so that a hydrogen atom is directly.
1 Alkynes contain a carbon-carbon triple bond. An alkyne has the general molecular formula C n H 2n−2, giving it four fewer hydrogens than the maximum.
Physical and Chemical Properties and Reactions of Alkenes and Alkynes.
John E. McMurry Paul D. Adams University of Arkansas Chapter 9 Alkynes: An Introduction to Organic Synthesis.
Alkynes: An Introduction to Organic Synthesis Based on McMurry’s Organic Chemistry, 7 th edition, Chapter 8.
Organic Chemistry William H. Brown & Christopher S. Foote.
CH 8 Alkynes: An Introduction to Organic Synthesis Renee Becker CHM 2210 Valencia Community College 1.
Bioorganic chemistry for General Medicine students Peoples’ Friendship University of Russia Faculty of Science L 2. Alkenes. Alkynes Groups ML-127/128.
Alkynes. Alkynes are molecules that incorporate a C C triple bond.
1 Organic Chemistry, Second Edition Janice Gorzynski Smith University of Hawai’i Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction.
IV. Oxidation Three types A. Epoxidation B. Hydroxylation C. Oxidative cleavage.
Chapter 10 Lecture Alcohols: Structure & Synthesis Organic Chemistry, 8 th Edition L. G. Wade, Jr.
T OPIC 4: A LKYNES : S TRUCTURE, R EACTIVITY AND S YNTHESIS Alkynes are hydrocarbons that contain a carbon-carbon triple bond, which is the strongest and.
1 Organic Chemistry, Third Edition Janice Gorzynski Smith University of Hawai’i Chapter 11 Lecture Outline Prepared by Layne A. Morsch The University of.
© 2016 Cengage Learning. All Rights Reserved. John E. McMurry Chapter 9 Alkynes: An Introduction to Organic Synthesis.
Alkynes.1Introduction.2Nomenclature of Alkynes.3Physical Properties of Alkynes.4Preparation of Alkynes.5Reactions of Alkynes.
Chapter 17 Aldehydes and Ketones II. Aldol Reactions.
© Prentice Hall 2001Chapter 31 Addition of Halogens The remaining halide ion is a good nucleophile which attacks the positively charged halonium ion.
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the -Carbon Irene Lee Case Western Reserve University.
205 Chapter 9: Alkynes 9.1: Sources of Alkynes (please read) 9.2: Nomenclature Systematic Nomenclature: Prefix-Parent-Suffix Naming Alkynes: Suffix: -yne.
Addition Reactions of Alkenes. The most characteristic reaction of alkenes is addition to the double bond. Addition Reactions of Alkenes.
© Prentice Hall 2001Chapter 31 Addition of Hydrogen Halides to Alkenes What about the following reaction? Which sp 2 carbon gets the hydrogen and which.
Chapter 9 Lecture Alkynes Organic Chemistry, 8 th Edition L. G. Wade, Jr.
Physical and Chemical Properties and Reactions of Alkenes and Alkynes CHAPTER NINE TERRENCE P. SHERLOCK BURLINGTON COUNTY COLLEGE 2004 CHE-240 Unit 3.
REACTIONS OF HYDROCARBONS REACTIONS OF ALKANES the single covalent bonds between carbon atoms in saturated and unsaturated hydrocarbons are difficult to.
CCAlkynes. Synthesis of Acetylene Heating coke with lime in an electric furnace to forms calcium carbide. Then drip water on the calcium carbide. coke.
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Chapter 4-3: Continue Alkynes: An Introduction to Organic Synthesis Based on: McMurry’s Organic Chemistry, 6 th edition, Chapter 4.
Alkenes, Alkynes. Required background: Thermodynamics from general chemistry Hybridization Molecular geometry Curved arrow notation Acidity and basicity.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 19 Carbonyl Compounds III Reactions at the -Carbon.
© Prentice Hall 2001Chapter 101 On Line Course Evaluation for Chemistry 350/Section We are participating in the online course evaluation Please log.
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Reactions of Unsaturated Hydrocarbons Combustion Complete combustion C 3 H 6 + O 2 → CO 2 + H 2 O Incomplete combustion C 3 H 6 + O 2 → C + CO + CO 2.
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