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  • 11 Arenes Lecture Example 1

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    Zul Abror Bin Ya'akop
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    This document provides an introduction to arenes, which are hydrocarbons containing one or more benzene rings. It discusses the key features of benzene, including its planar structure, sp2 hybridized carbon atoms, and delocalized pi electron cloud. The document covers nomenclature rules for compounds containing benzene rings. It also describes the electrophilic substitution reactions of benzene, such as nitration and halogenation, noting that these substitutions preserve the stable delocalized pi system. Electrophilic catalysts like FeBr3 are used to generate stronger electrophiles to facilitate these substitution reactions.

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    This document provides an introduction to arenes, which are hydrocarbons containing one or more benzene rings. It discusses the key features of benzene, including its planar structure, sp2 hybridized carbon atoms, and delocalized pi electron cloud. The document covers nomenclature rules for compounds containing benzene rings. It also describes the electrophilic substitution reactions of benzene, such as nitration and halogenation, noting that these substitutions preserve the stable delocalized pi system. Electrophilic catalysts like FeBr3 are used to generate stronger electrophiles to facilitate these substitution reactions.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    7 views8 pages

    11 Arenes Lecture Example 1

    Uploaded by

    Zul Abror Bin Ya'akop
    This document provides an introduction to arenes, which are hydrocarbons containing one or more benzene rings. It discusses the key features of benzene, including its planar structure, sp2 hybridized carbon atoms, and delocalized pi electron cloud. The document covers nomenclature rules for compounds containing benzene rings. It also describes the electrophilic substitution reactions of benzene, such as nitration and halogenation, noting that these substitutions preserve the stable delocalized pi system. Electrophilic catalysts like FeBr3 are used to generate stronger electrophiles to facilitate these substitution reactions.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    of 8

    8/22/2012

    Arenes
    2012 C1 Chemistry Lecture 1

    Introduction
    Pg 2

    What are arenes? Hydrocarbons that contain one or more benzene rings What does the term aromatic mean? Aromatic compounds refer to benzene and other compounds stabilized by a ring system of delocalized electrons

    8/22/2012

    Independent Learning Subtopic


    Pg 3-6

    5 Things about benzene:


    C6H6 Planar molecule Each C atom is sp2 hybridised 6 unhybridised p orbitals overlap to form a delocalised electron cloud above and below plane of the ring Delocalised electron cloud confers extra stability onto benzene

    Nomenclature
    Pg 6-7

    When is benzene the parent chain?


    benzene

    When is benzene the substituent?


    phenyl

    Note the traditional names of common compounds containing benzene. (e.g. phenol, benzaldehyde, benzoic acid) If you have more than one substituent on the benzene ring,
    principal functional group at position 1 achieve lowest numbers

    8/22/2012

    Nomenclature
    Pg 8

    Reactions of Benzene
    Pg 8

    Electrophilic Substitution
    Why Electrophilic?
    Rich source of electrons above and below the plane of the ring

    Why Substitution?
    Delocalized electron cloud confers extra stability Loss of aromaticity energetically unfavorable Benzene does not undergo addition reactions (unlike alkenes)

    8/22/2012

    Electrophilic Substitution
    Pg 8

    To preserve the stable delocalized system:

    Pg 9

    Electrophilic Substitution: Nitration


    Pg 9

    8/22/2012

    Pg 10

    Electrophilic Substitution: Nitration


    Pg 10

    Energy profile diagram:

    8/22/2012

    Electrophilic Substitution
    Pg 11

    Shape and hybridization changes in the mechanism

    Electrophilic Substitution
    Pg 11

    8/22/2012

    Electrophilic Substitution: Halogenation


    Pg 12

    Lewis acid catalysts: FeBr3, AlBr3


    Electron pair acceptors Generate stronger electrophile Br+

    Can add iron filings instead of FeBr3 to generate catalyst FeBr3 in situ: 2Fe(s) + 3Br2(l) 2FeBr3(s) Chlorination: Cl2, FeCl3 (or AlCl3), warm

    Pg 13

    8/22/2012

    Pg 13

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