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    12.5 Reactions in Organic Compounds 1

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    AisyahiraMelanOmar
    This document discusses organic reactions and reaction intermediates. It explains that reactions occur through homolytic or heterolytic bond cleavage to form radicals or ions. Carbocations are more stable with more alkyl groups due to inductive effects. Electrophiles are electron-deficient and attack electron-rich sites, while nucleophiles are electron-rich and attack sites of low electron density. Examples of each type are provided.

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    12.5 Reactions in Organic Compounds 1

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    AisyahiraMelanOmar
    87 views13 pages
    This document discusses organic reactions and reaction intermediates. It explains that reactions occur through homolytic or heterolytic bond cleavage to form radicals or ions. Carbocations are more stable with more alkyl groups due to inductive effects. Electrophiles are electron-deficient and attack electron-rich sites, while nucleophiles are electron-rich and attack sites of low electron density. Examples of each type are provided.

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    This document discusses organic reactions and reaction intermediates. It explains that reactions occur through homolytic or heterolytic bond cleavage to form radicals or ions. Carbocations are more stable with more alkyl groups due to inductive effects. Electrophiles are electron-deficient and attack electron-rich sites, while nucleophiles are electron-rich and attack sites of low electron density. Examples of each type are provided.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    87 views13 pages

    12.5 Reactions in Organic Compounds 1

    Uploaded by

    AisyahiraMelanOmar
    This document discusses organic reactions and reaction intermediates. It explains that reactions occur through homolytic or heterolytic bond cleavage to form radicals or ions. Carbocations are more stable with more alkyl groups due to inductive effects. Electrophiles are electron-deficient and attack electron-rich sites, while nucleophiles are electron-rich and attack sites of low electron density. Examples of each type are provided.

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    of 13

    12.

    5 REACTION IN ORGANIC COMPOUNDS

    C H E M I S T RY U N I T
    SK027
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    OBJECTIVES:
    1.Explain covalent bond cleavage:
    • homolytic cleavage to produce free radicals
    • Heterolytic cleavage to produce carbocation and
    anion
    2. State the relative stabilities of 1o,2o,3o
    • Carbocations/Carboniums
    • Free radicals
    • Carbanions
    Explain the inductive effect of alkyl group towards
    the stability of carbocations and carbanions.
    S K 0 2 7 C H E M I S T RY
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    OBJECTIVES:

    3. Define electrophile and nucleophile


    i. types of electrophiles: Lewis acids, cations
    and electron deficient sites in organic compounds
    ii. types of nucleophiles: Lewis base,anions and
    electron rich sites in organic compounds

    S K 0 2 7 C H E M I S T RY
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    COVALENT BOND CLEAVAGE / FISSION


    • All chemical reactions involved bond-breaking
    and bond-forming .
    • Reactions occur at the active site/functional
    group.
    • Reactive intermediate occurs in the course of
    reaction
    • Types of covalent bond cleavage:
    a. Homolytic cleavage
    b. Heterolytic cleavage

    S K 0 2 7 C H E M I S T RY
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    HOMOLYTIC CLEAVAGE
    • ..is a bond fission in which the two shared
    electrons of the covalent bond are split equally
    between the two atoms.
    • Occurs in a non-polar bond involving two atoms
    of similar electronegativity.
    • Free radicals (atoms/group of atoms contains
    an unpaired valence electron) are formed.
    Example:
    uv
    Cl Cl Cl + Cl
    S K 0 2 7 C H E M I S T RY
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    HETEROLYTIC CLEAVAGE
    • .. Is the bond-breakage in which both electrons
    remain on one of the atoms.
    • Occurs in a polar bond involving two atoms of
    different electronegativities.
    • Cation and anion are formed.
    Example: C Br C + Br

    Carbocation / carbonium

    C E C + E
    Carbanion
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    R
    CH3 < R CH2 < R CH <
    R C
    R R
    R
    CH 3 < R CH 2 < R CH < R C
    R R

    Methyl < 1° < 2° < 3°


    • The stability of carbocation & free radical increases with
    the number of alkyl groups present.
    • The alkyl groups are electron-releasing, thus help to
    stabilize the +ve charge on the carbocation / free radical.
    • This is called the inductive effect
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Relative Stabilities of intermediates

    - R
    - - -
    CH 3 > R CH 2 > R CH > R C
    R R

    Methyl > 1° > 2° > 3°


    • The alkyl group decreases the stability of a carbanion
    • The greater the number of alkyl group, the less stable
    is the carbanion
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Reagents and sites of organic reactions


    a) Electrophile
    • ..is an electron-deficient species which capable of
    accepting electron pairs.
    • it attacks electron-rich areas of organic molecules.
    • can be either neutral or positively charged.
    Type Example
    Cations NO2+, H3O+
    Lewis acid AlCl3, BF3
    Carbocation C+
    Oxidising agents Br2, Cl2
    Site of low e density δ+ δ- δ+ δ- δ+ δ-
    C=O C–X C – OH
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Reagents and sites of organic reactions


    b) Nucleophile
    • ..is an electron-rich species which is capable of donating
    electron pairs.
    • it attacks low electron density areas of organic molecules.
    • can be either neutral or negatively charged.
    Type Example
    Anions OH-, RO-, Cl-, CN-
    Lewis base NH3, H2O, H2S
    Carbanion C-
    Site of high e density Benzene
    C=C C C
    ring
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Exercises: 1. The bond dissociation energies for homolytic


    cleavage are as below,
    Bond Bond dissociation
    energies (kJmol-1)
    CH3 H 435
    CH3CH2 H 410
    C6H5CH2 H 356
    (CH3)2C H 397
    (CH3)3C H 381
    What is homolytic cleavage, write the free radicals that are
    formed due to the homolytic cleavage and rank them
    increasing order of stability.
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Exercises: 2. a) Classify the following species as free


    radical, carbonium ion, carbanion,
    electrophile or nucleophile.
    i) (CH3)2CH-
    ii) CH3CH2•
    iii) CH3O-
    iv) NO2+
    v) (CH3)3C+

    b) Ethane reacts with bromine according to the equation


    CH3CH3 + Br2 → CH3CH2Br + HBr
    i) Classify this reaction
    ii) Write the structural formula of the organic species
    formed when CH3CH3 undergoes homolytic fission.
    iii) Write the structural formulae of the species formed
    when CH3CH2Br undergoes heterolytic fission.
    C H A P T E R 1 2 : I N T R O D U C T I O N T O O R G A N I C C H E M I S T RY

    12.5 REACTION IN ORGANIC COMPOUNDS

    Exercises:
    3. (a) Explain how free radicals are formed. Write an
    equation for the bromine-bromine bond cleavage
    in the bromination of methane. State the type of
    bond cleavage.
    (b) Which of the following species is likely to be an
    electrophile, and which a nucleophile ?
    CH3OCH2CH3, AlCl3, CH3OH, NH3,

    C6H5N2+, (CH3)CH2+ ,OH- ,

    CH3CH=CH2,

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