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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.
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© 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.
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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.
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Alkynes: An Introduction to Organic Synthesis Based on McMurry’s Organic Chemistry, 7 th edition, Chapter 8.
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© Prentice Hall 2001Chapter 31 Addition of Halogens The remaining halide ion is a good nucleophile which attacks the positively charged halonium ion.
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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.
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© 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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