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    CHAPTER 2 Extra Cycloalkanes

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    ellina safian
    Cycloalkanes are cyclic alkanes containing rings of carbon atoms. Examples include cyclobutane and cyclohexane. They are named like acyclic alkanes with the prefix "cyclo-" to indicate the ring. If there is more than one substituent, the carbons are numbered to give the lowest numbers to substituted carbons. Cycloalkanes can exist as cis or trans isomers depending on the orientation of substituents. Smaller rings like cyclopropane experience more angle strain and reactivity than larger rings.

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    CHAPTER 2 Extra Cycloalkanes

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    ellina safian
    113 views13 pages
    Cycloalkanes are cyclic alkanes containing rings of carbon atoms. Examples include cyclobutane and cyclohexane. They are named like acyclic alkanes with the prefix "cyclo-" to indicate the ring. If there is more than one substituent, the carbons are numbered to give the lowest numbers to substituted carbons. Cycloalkanes can exist as cis or trans isomers depending on the orientation of substituents. Smaller rings like cyclopropane experience more angle strain and reactivity than larger rings.

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    CHAPTER 2 extra cycloalkanes

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    Cycloalkanes are cyclic alkanes containing rings of carbon atoms. Examples include cyclobutane and cyclohexane. They are named like acyclic alkanes with the prefix "cyclo-" to indicate the ring. If there is more than one substituent, the carbons are numbered to give the lowest numbers to substituted carbons. Cycloalkanes can exist as cis or trans isomers depending on the orientation of substituents. Smaller rings like cyclopropane experience more angle strain and reactivity than larger rings.

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    113 views13 pages

    CHAPTER 2 Extra Cycloalkanes

    Uploaded by

    ellina safian
    Cycloalkanes are cyclic alkanes containing rings of carbon atoms. Examples include cyclobutane and cyclohexane. They are named like acyclic alkanes with the prefix "cyclo-" to indicate the ring. If there is more than one substituent, the carbons are numbered to give the lowest numbers to substituted carbons. Cycloalkanes can exist as cis or trans isomers depending on the orientation of substituents. Smaller rings like cyclopropane experience more angle strain and reactivity than larger rings.

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    of 13

    CYCLOALKANES

     Cyclic compound: A compound in which a series of


    atoms is connected to form a loop or ring.
     Cycloalkanes: Alkanes that contain rings of carbon
    atoms.
     Examples:

    H H
    H
    H
    C
    C C
    H H
    C C H
    H
    C
    H H
    H H
    cyclobutane cyclohexane
    NOMENCLATURE OF
    CYCLOALKANES
    1. Named like acyclic (noncyclic) alkanes, with the prefix cyclo-
    indicating the presence of a ring.

    2. If there is just one substituent, no numbering is needed.

    For examples:

    CH3 Br

    methylcyclohexane isopropylcyclohexane bromocyclopentane ethylcyclobutane


    CONTINUE..
    3. If there are two or more substituents on the ring, the ring
    carbons are numbered to give the lowest possible numbers
    for the substituted carbons.

    4. In the name, the substituents are listed in alphabetical order.

    5. When the numbering could begin with either of two alkyl


    groups (as in disubstituted cycloalkanes), begin with the
    one that is alphabetically first.
    EXAMPLES..
    1
    CH3
    CORRECT
    4 32
    5 1 1-ethyl-3-methylcyclohexane
    6
    CH2CH3 (lowest possible numbers of substituents)

    CH3
    INCORRECT
    45 6
    32 1
    1-ethyl-5-methylcyclohexane
    CH2CH3

    CH3 INCORRECT
    3-ethyl-1-methylcyclohexane
    6 12
    5
    4 3
    CH2CH3 (begin with the one that is alphabetically first)
    EXAMPLES..
    2 CH3 CH3 1,1,3-trimethylcyclopentane
    1 (carbon 1 = carbon that attached to many
    5 2 substituents)
    3
    4
    CH3
    3
    CH3
    1 2 Br CORRECT
    6
    2-bromo-4-chloro-1-methylcyclohexane
    5 3
    4 (lowest possible numbers of substituents)
    Cl

    CH3
    4 Br
    5
    3 INCORRECT
    6 2
    1 3-bromo-1-chloro-4-methylcyclohexane
    Cl
    CONTINUE..
    6. If longest carbon chain: Acyclic > cyclic
    Or
     Acyclic contain an important functional group

    So, the CYCLIC PORTION will be the substituent group


    and name as cycloalkyl group.

    Examples:

    H C C CH2 CH2 CH2

    4-cyclopropyl-3-methyloctane 5-cyclobutyl-1-pentyne
    CIS / TRANS
     Less flexible than their open-chain
     Two isomers:
    i) cis – two substituents point toward the same
    direction.
    ii) trans - two substituents point toward opposite
    direction.
     Example:
    CYCLOALKANES

    RING
    SUBSTITUTION
    OPENING
    - LARGE RING
    - SMALL RING
    - >C3
    - C3
    RING OPENING
    (SMALL RING)
    Ni, H2
    CH3CH2CH3
    o
    80 C
    X Br2, CCl4
    CH2BrCH2CH2Br

    H3O+
    Y CH3CH2CH2OH

    HI
    CH3CH2CH2I
    SUBSTITUTIONS
    (LARGE RING)
    • Example
    H Cl
    + Cl2 uv + HCl

    a)
    i) Initiation
    Cl Cl uv 2Cl •

    ii) Propagation
    H
    •
    Cl • + + HCl

    • Cl
    + Cl2 + Cl•

    iii) Termination
    Cl• + Cl • Cl2
    CONTINUE..

    Three-dimensional structure of some cycloalkanes

    11
    RING STRAIN

    Bond angle :
    cyclopropane < cyclobutane < cyclopentane

    Angle strain :
    cyclopropane > cyclobutane > cyclopentane

    Reactivity :
    cyclopropane > cyclobutane > cyclopentane
    12
    THE
    END

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