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10: Organohalides

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    Learning Objectives

    After you have completed Chapter 10, you should be able to

    • fulfill all of the detailed objectives listed under each individual section.
    • design a multistep synthesis to prepare a given compound from a given starting material using any of the reactions studied up to this point in the course, including those which involve alkyl halides.
    • solve road-map problems requiring a knowledge of any of the reactions or concepts studied up to this point, including those introduced in this chapter.
    • define, and use in context, the key terms introduced.

    • 10.0: Introduction to Organohalides
      Many organic compounds are closely related to the alkanes. Alkanes react with halogens to produce halogenated hydrocarbons, the simplest of which have a single halogen atom substituted for a hydrogen atom of the alkane. Even more closely related are the cycloalkanes, compounds in which the carbon atoms are joined in a ring, or cyclic fashion.
    • 10.1: Names and Properties of Alkyl Halides
      Alkyl halides are also known as haloalkanes. This page explains what they are and discusses their physical properties. alkyl halides are compounds in which one or more hydrogen atoms in an alkane have been replaced by halogen atoms (fluorine, chlorine, bromine or iodine).
    • 10.2: Preparing Alkyl Halides from Alkanes - Radical Halogenation
      Alkanes (the simplest of all organic compounds) undergo very few reactions. One of these reactions is halogenation, or the substitution of a single hydrogen on the alkane for a single halogen to form a haloalkane. This reaction is very important in organic chemistry because it functionalizes alkanes which opens a gateway to further chemical reactions.
    • 10.3: Preparing Alkyl Halides from Alkenes - Allylic Bromination
    • 10.4: Stability of the Allyl Radical - Resonance Revisited
    • 10.5: Preparing Alkyl Halides from Alcohols
      This page looks at reactions in which the -OH group in an alcohol is replaced by a halogen such as chlorine or bromine. It includes a simple test for an -OH group using phosphorus(V) chloride.
    • 10.6: Reactions of Alkyl Halides - Grignard Reagents
      The organomagnesium compounds formed by the reaction of an alkyl or aryl halide with magnesium are called Grignard reagents. As you will see throughout the remainder of this course, Grignard reagents can be used to synthesize a wide range of organic compounds and are extremely useful to the organic chemist.
    • 10.7: Organometallic Coupling Reactions
    • 10.8: Oxidation and Reduction in Organic Chemistry
      In organic chemistry, redox reactions look a little different. Electrons in an organic redox reaction often are transferred in the form of a hydride ion - a proton and two electrons. Because they occur in conjunction with the transfer of a proton, these are commonly referred to as hydrogenation and dehydrogenation reactions: a hydride plus a proton adds up to a hydrogen (H2) molecule. Be careful - do not confuse the terms hydrogenation and dehydrogenation with hydration and dehydration.
    • 10.S: Organohalides (Summary)

    10: Organohalides is shared under a CC BY-SA 4.0 license and was authored, remixed, and/or curated by Steven Farmer & Dietmar Kennepohl.