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    Organohalides: Based On Mcmurry'S Organic Chemistry, 7 Edition

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    AYALEYDEN
    This document defines alkyl halides and discusses their properties, structures, and methods of preparation. It also introduces oxidation and reduction reactions in organic chemistry. Key points include: - Alkyl halides contain carbon-halogen bonds and are used as solvents, refrigerants, and in pharmaceuticals. - They undergo nucleophilic substitution and elimination reactions studied in this chapter as models for more complex reactions. - Methods of preparing alkyl halides include radical halogenation of alkenes and alkanes, and reaction of tertiary alcohols with hydrogen halides. - Oxidation in organic chemistry replaces carbon-hydrogen or carbon-carbon bonds with carbon-oxygen/nitrogen

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    Organohalides: Based On Mcmurry'S Organic Chemistry, 7 Edition

    Uploaded by

    AYALEYDEN
    84 views13 pages
    This document defines alkyl halides and discusses their properties, structures, and methods of preparation. It also introduces oxidation and reduction reactions in organic chemistry. Key points include: - Alkyl halides contain carbon-halogen bonds and are used as solvents, refrigerants, and in pharmaceuticals. - They undergo nucleophilic substitution and elimination reactions studied in this chapter as models for more complex reactions. - Methods of preparing alkyl halides include radical halogenation of alkenes and alkanes, and reaction of tertiary alcohols with hydrogen halides. - Oxidation in organic chemistry replaces carbon-hydrogen or carbon-carbon bonds with carbon-oxygen/nitrogen

    Original Title

    Chapter 3.1 - Alkylhalides

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    This document defines alkyl halides and discusses their properties, structures, and methods of preparation. It also introduces oxidation and reduction reactions in organic chemistry. Key points include: - Alkyl halides contain carbon-halogen bonds and are used as solvents, refrigerants, and in pharmaceuticals. - They undergo nucleophilic substitution and elimination reactions studied in this chapter as models for more complex reactions. - Methods of preparing alkyl halides include radical halogenation of alkenes and alkanes, and reaction of tertiary alcohols with hydrogen halides. - Oxidation in organic chemistry replaces carbon-hydrogen or carbon-carbon bonds with carbon-oxygen/nitrogen

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    84 views13 pages

    Organohalides: Based On Mcmurry'S Organic Chemistry, 7 Edition

    Uploaded by

    AYALEYDEN
    This document defines alkyl halides and discusses their properties, structures, and methods of preparation. It also introduces oxidation and reduction reactions in organic chemistry. Key points include: - Alkyl halides contain carbon-halogen bonds and are used as solvents, refrigerants, and in pharmaceuticals. - They undergo nucleophilic substitution and elimination reactions studied in this chapter as models for more complex reactions. - Methods of preparing alkyl halides include radical halogenation of alkenes and alkanes, and reaction of tertiary alcohols with hydrogen halides. - Oxidation in organic chemistry replaces carbon-hydrogen or carbon-carbon bonds with carbon-oxygen/nitrogen

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    © All Rights Reserved
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    of 13

    10.

    Organohalides

    Based on McMurry’s Organic Chemistry, 7th edition


    What Is an Alkyl Halide
     An organic compound containing at least one carbon-
    halogen bond (C-X)
     X (F, Cl, Br, I) replaces H
     Can contain many C-X bonds
     Properties and some uses
     Fire-resistant solvents
     Refrigerants
     Pharmaceuticals and precursors

    2
    Why this Chapter?
     Reactions involving organohalides are less
    frequently encountered than other organic
    compounds, but reactions such as
    nucleophilic substitutions/eliminations that
    they undergo will be encountered
     Alkyl halide chemistry is model for
    mechanistically similar but more complex

    3
    10.1 Naming Alkyl Halides
     Find longest chain, name it as parent chain
     Number from end nearest any substituent (alkyl or
    halogen)

    4
    Naming if Two Halides or Alkyl Are
    Equally Distant from Ends of Chain
     Begin at the end nearer the substituent whose name
    comes first in the alphabet

    5
    10.2 Structure of Alkyl Halides
     C-X bond is longer as you go down periodic table
     C-X bond is weaker as you go down periodic table
     C-X bond is polarized with slight positive on carbon
    and slight negative on halogen

    6
    10.3 Preparing Alkyl Halides from
    Alkenes: Radical Halogenation
     Alkyl halide from addition of HCl, HBr, HI to alkenes
    to give Markovnikov product (see Alkenes chapter)

    7
    10.3 Preparing Alkyl Halides from
    Alkanes: Radical Halogenation
     Alkane + Cl2 or Br2, heat or light replaces C-H with C-
    X but gives mixtures
     Hard to control
     Via free radical mechanism

    8
    Relative Reactivity
     Based on quantitative analysis of reaction products,
    relative reactivity is estimated
     Order parallels stability of radicals
     Reaction distinction is more selective with bromine
    than chlorine

    9
    10.6 Preparing Alkyl Halides from
    Alcohols
     Reaction of tertiary C-OH with HX is fast and
    effective
     Add HCl or HBr gas into ether solution of tertiary
    alcohol
     Primary and secondary alcohols react very slowly
    and often rearrange, so alternative methods are used

    10
    10.9 Oxidation and Reduction in
    Organic Chemistry
     In organic chemistry, we say that oxidation occurs
    when a carbon or hydrogen that is connected to a
    carbon atom in a structure is replaced by oxygen,
    nitrogen, or halogen
     Oxidation is a reaction that results in loss of electron
    density at carbon (as more electronegative atoms
    replace hydrogen or carbon)

    Oxidation: break C-H (or C-C) and form C-O,


    C-N, C-X

    11
    Reduction Reactions
     Organic reduction is the opposite of oxidation
     Results in gain of electron density at carbon
    (replacement of electronegative atoms by
    hydrogen or carbon)
    Reduction: form C-H (or C-C) and break C-O, C-N, C-X

    second reaction at top of p. 349 here

    12
    Oxidation Levels
     Functional groups are associated with specific levels

    13

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