Organic Chemistry: Reactions and Bond Cleavage
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Questions and Answers

What type of cleavage results in one fragment receiving both electrons from the broken bond?

  • Radical cleavage
  • Heterolytic cleavage (correct)
  • Homolytic cleavage
  • Ionic cleavage

    • What is a species with a carbon atom possessing a sextet of electrons and a positive charge called?

  • Carbanion
  • Radical
  • Carbocation (correct)
  • Carbonate

    • Which of the following is a tertiary carbocation?

  • (CH3)2C+H
  • C+H3
  • (CH3)3C+ (correct)
  • CH3C+H2

    • What is the observed order of carbocation stability from least to most stable?

    <p>C+H3 &lt; CH3C+H2 &lt; (CH3)2C+H &lt; (CH3)3C+ (D)</p> Signup and view all the answers

    What hybridization is observed in a carbocation?

    <p>sp2 (C)</p> Signup and view all the answers

    What stabilizing effects contribute to carbocation stability?

    <p>Inductive and hyperconjugation effects (A)</p> Signup and view all the answers

    What defines the term 'substrate' in an organic reaction?

    <p>The organic molecule that provides carbon to the new bond (D)</p> Signup and view all the answers

    What is formed after the heterolytic cleavage of a covalent bond in bromomethane?

    <p>C+H3 and Br- (C)</p> Signup and view all the answers

    In an organic reaction, the organic molecule is also referred to as a ______.

    <p>substrate</p> Signup and view all the answers

    Heterolytic cleavage results in one fragment having a ______ charge.

    <p>positive</p> Signup and view all the answers

    A carbocation with one carbon directly attached is classified as a ______ carbocation.

    <p>primary</p> Signup and view all the answers

    The structure of carbocations is typically ______ planar.

    <p>trigonal</p> Signup and view all the answers

    Alkyl groups stabilize carbocations through inductive and ______ effects.

    <p>hyperconjugation</p> Signup and view all the answers

    After heterolysis of bromomethane, the products are CH3 and ______.

    <p>Br–</p> Signup and view all the answers

    The positive charge in a carbocation is carried by a carbon atom with a sextet of ______.

    <p>electrons</p> Signup and view all the answers

    The observed order of carbocation stability is C+H3 < CH3C+H2 < ______.

    <p>(CH3)2C+H</p> Signup and view all the answers

    Flashcards

    Organic Reaction

    A reaction where an organic molecule (substrate) reacts with a reagent to form intermediate(s) and final product(s).

    Substrate

    The reactant in an organic reaction which provides carbon for the new bond.

    Reagent

    The reactant in an organic reaction that attacks the substrate.

    Heterolytic Cleavage

    Breaking a covalent bond where the shared electron pair goes to one fragment (creating ions).

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    Carbocation

    A positively charged carbon atom with a sextet of electrons.

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    Carbocation Stability

    Tertiary carbocations are more stable than secondary, which are more stable than primary.

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    Primary Carbocation

    A carbocation where only one carbon atom is attached to the positively charged carbon.

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    Tertiary Carbocation

    A carbocation with three carbon atoms attached directly to the positively charged carbon.

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    Homolytic Cleavage

    Breaking a covalent bond where each atom gets one of the shared electrons, forming radicals.

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    Radicals

    Atoms or molecules with an unpaired electron, making them highly reactive.

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    Secondary Carbocation

    A carbocation with two carbon atoms directly bonded to the positively charged carbon.

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    Study Notes

    Organic Reactions

    • Organic molecules (substrates) react with reagents to form intermediates and products.
    • A reactant supplying carbon to a new bond is the substrate. If both reactants contribute, the choice is arbitrary.
    • Reactions involve breaking a carbon-carbon or carbon-other atom bond and forming a new bond.
    • Reaction mechanisms detail each step, electron movement, energy changes, and reaction rates.

    Bond Cleavage

    • Covalent bonds can cleave through heterolytic or homolytic fission.
    • Heterolytic cleavage: The shared electron pair remains with one fragment.
    • Heterolysis creates a positively charged fragment (sextet) and a negatively charged fragment (octet).
    • Example: Bromomethane (CH3Br) heterolytically cleaves into CH3+ and Br-.
    • A carbocation is a carbon with a sextet and a positive charge.
    • Carbocation classifications:
      • Primary (one carbon attached)
      • Secondary (two carbons attached)
      • Tertiary (three carbons attached)
    • CH3+ (methyl cation) is a primary carbocation.
    • Carbocations are highly unstable and reactive.
    • Alkyl groups stabilize carbocations through inductive and hyperconjugation effects.
    • Carbocation stability: Methyl < Ethyl < Isopropyl < Tert-butyl
    • Carbocation shape: Trigonal planar (sp2 hybridized carbon).

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    Description

    Explore the fundamental concepts of organic reactions, including the roles of substrates and the details of reaction mechanisms. This quiz delves into bond cleavage types, such as heterolytic and homolytic fission, and provides insights into carbocation classifications. Test your understanding of these essential organic chemistry topics.

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