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    This document provides information on alkyl halides, including their nomenclature, methods of preparation from alkanes, alcohols and alkenes, and their physical and chemical properties. Alkyl halides are polarized, with the carbon bearing a partial positive charge and the halogen a partial negative charge. This makes them reactive toward nucleophilic substitution reactions, where the halide is replaced by other nucleophiles such as hydroxide, alkoxide, cyanide, or organometallic reagents. Common organometallic reagents used to prepare organometallic compounds from alkyl halides include Grignard reagents (RMgX) and organolithium compounds (RLi).

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    4 views10 pages
    This document provides information on alkyl halides, including their nomenclature, methods of preparation from alkanes, alcohols and alkenes, and their physical and chemical properties. Alkyl halides are polarized, with the carbon bearing a partial positive charge and the halogen a partial negative charge. This makes them reactive toward nucleophilic substitution reactions, where the halide is replaced by other nucleophiles such as hydroxide, alkoxide, cyanide, or organometallic reagents. Common organometallic reagents used to prepare organometallic compounds from alkyl halides include Grignard reagents (RMgX) and organolithium compounds (RLi).

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    This document provides information on alkyl halides, including their nomenclature, methods of preparation from alkanes, alcohols and alkenes, and their physical and chemical properties. Alkyl halides are polarized, with the carbon bearing a partial positive charge and the halogen a partial negative charge. This makes them reactive toward nucleophilic substitution reactions, where the halide is replaced by other nucleophiles such as hydroxide, alkoxide, cyanide, or organometallic reagents. Common organometallic reagents used to prepare organometallic compounds from alkyl halides include Grignard reagents (RMgX) and organolithium compounds (RLi).

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    © All Rights Reserved
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    4 views10 pages

    14

    Uploaded by

    Hasen umer
    This document provides information on alkyl halides, including their nomenclature, methods of preparation from alkanes, alcohols and alkenes, and their physical and chemical properties. Alkyl halides are polarized, with the carbon bearing a partial positive charge and the halogen a partial negative charge. This makes them reactive toward nucleophilic substitution reactions, where the halide is replaced by other nucleophiles such as hydroxide, alkoxide, cyanide, or organometallic reagents. Common organometallic reagents used to prepare organometallic compounds from alkyl halides include Grignard reagents (RMgX) and organolithium compounds (RLi).

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    Alkyl halides RX

    Classification of alkyl halides:

    CH3 H3C
    H2
    C
    CH H3C C
    H3C Br
    H3C Br Br
    H3C
    ● Nomenclature
    • IUPAC Name
    ⃰ X substituent not functional group
    Step (1)-Find the longest chain and name it as the parent
    (if double bond or triple bond is present the parent must
    contain it).
    Step (2)-Number the carbons of the parent chain beginning
    at the end nearer to the first substituent whether alkyl or
    halogen.

    Br

    I Cl
    Cl

    2-Iodo-2-methylbutane 3-Choro-2-methylpentane 1-bromo-3-chloro-4-methylpentane


    ( tert. pentyl iodide)
    Step (3)-If the parent can be numbered from either end by step 2
    begin from the end nearer the substituent that has alphabetical
    precedence.
    Br

    2-bromo-5-methylhexane

    • Preparation of alkyl halides:-

    1.Free radical halogenation of alkanes:-


    ● with Br2 or Cl2
    ● Br2 more selective while Cl2 more reactive.
    H3C H3C

    Br2 hv
    H3C H + H3C Br

    H3C H3C
    tert-butyl bromide
    99%
    hv
    CH3CH2CH3 + Cl2 CH3CHClCH3 + CH3CH2CH2Cl
    55% 45%

    ●●● Allylic halogenation:-


    NBS
    CH3CH=CH2 BrCH2CH=CH2 allyl bromide

    2- Hydrohalogenation of alkenes:

    HI >HBr >HCl >HF (dry gases)


    Allow Markonikov’s rule
    3-From Alcohols:
    a) By using Hydrogen Halides:-
    ROH + HX RX + H2O

    30 20 10 HI HBr HCl HF

    Reaction is acid catalyzed (SN1 mechanism)

    CH3CH2CH2OH + HBr CH3CH2CH2Br + H2O

    H3C H3C CH3


    CH3
    HCl
    H3C H3C CH2
    CH2

    HO Cl
    b) By using PBr3 or SOCl2:-

    ROH + PBr3 RBr + H3PO3

    • Milder conditions.
    • less likely to cause acid catalyzed rearrangement.
    PBr3
    CH3CH2CHCH3 CH3CH2CHCH3 + H3PO3

    OH Br

    Cl
    OH
    SOCl2

    + SO2 + HCl
    O
    O

    Physical properties:-
    • RX have higher mol. Wt than corresponding alkanes so have higher B.P.
    • For a given R, b.p. increases as atomic weight of X increases so
    b.p. for RI > RBr > RCl > RF
    • RX insoluble in water, soluble in nonpolar solvent.
    Polarity of C–X bond:

    1) The carbon-halogen bond of alkyl halides is polarized (due


    difference in electronegativity).
    2) The carbon atom bears a partial positive charge, the halogen atom
    a partial negative charge.
    Reactions of Alkyl halides
    • RX reactive towards Nucleophilic Substitution reactions
    (SN1 & SN2)
    OH ROH
    SN2 Reactions

    R'O ROR'

    CN RCN

    SH RSH

    R'C C
    RX RC CR'

    (R= Me, 10 or 20)


    R'COO R'COOR

    I
    RI

    N3
    RN3

    NH3
    RNH2
    Organometallic Compounds
    Compounds have C-M bond.
    C-M ranging from ionic to primarily covalent bonds
    according to the difference in EN.
    δ δ C M
    C: M C: M

    ionic partially ionic covalent


    M= Na or K M= Mg or Li M= Ag, Cu or Cd
    Preparation:
    Mg (Grignard reagent)
    RMgX
    ether
    RX
    2 Li
    RLi + LiX
    ether

    RMgX + CdCl2 MgCl2 + RCdCl (Organocadmium compounds)

    RLi + CuI liI + R2CuLi (Lithium dialkyl copper)

    ● R may be (1o , 2o ,3o), cycloalkyl .


    ● Order of reactivity of RX
    RI > RBr > RCl > RF
    ● Solvent must be anhydrous (usually ether or THF).

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