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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
ORGANIC OPTION -G. IB Core Option Objective Electrophilic Addition Reactions G.1.1 Describe and explain the electrophilic addition mechanisms of the reactions.
Topic 27 Topic 27 Topic 27: Hydrocarbons Table of Contents Topic 27 Topic 27 Basic Concepts Additional Concepts.
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HL O PTION G O RGANIC C HEMISTRY. IB HL O PTION O BJECTIVE G.9.1 Describe, using equations, the reactions of acid anhydrides with nucleophiles to form.
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William L Masterton Cecile N. Hurley Edward J. Neth University of Connecticut Chapter 16 Precipitation.
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SAT II CHEM PREP PPT Mrs. Gupta Modified from Mark Rosengartens Powerpoint.
Aqueous Equilibria Chapter 17 Additional Acid/ Base Equilibria Buffers Common Ion Effects Solubility Complex ion formation.
N ATURE ’ S C HEMISTRY Oxidation of Food. A LCOHOLS Alcohols make up a group of organic compounds which contain the -OH group, called the hydroxyl group.
Reactions of alkanes, alkenes, alkynes and aromatics.
Ch. 18: Acids & Bases Sec. 18.1: Acids & Bases: An Introduction.
Compounds of Carbon Chapter 8. Why is carbon important? Carbon makes up over 90% of all chemical compounds Carbon makes up over 90% of all chemical compounds.
CHAPTER 8 INTRODUCTION TO ORGANIC CHEMISTRY BASIC CHEMISTRY CHM 138.
Organic Nomenclature Compounds in which carbon is the principal element.
Chapter 7Mr. Kennedy. What is a solution? Solution-well-mixed mixture containing a solvent and at least one solute that has the same properties throughout.
Chemical reactions occur when bonds (between the electrons of atoms) are formed or broken Chemical reactions involve changes in the chemical composition.
Functional Groups, Orbitals, and Geometry. Resonance Structures.
Chemical Bonding. Why the noble gaes are so noble… The elements in group 18 are known as the noble gases. They are completely unreactive The other elements.
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