suggest why 1-chlorobutane reacts with water via a different mechanism.

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  1. xXxiKillxXx's Avatar
    • Overlord in Training
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    suggest why 1-chlorobutane reacts with water via a different mechanism.
    suggest why 1-chlorobutane reacts with water via a different mechanism.

    My book doesn't cover this at all, what exactly are we supposed to talk about?
    I checked the mark scheme, it says something about 1-chlorobutane being a primary halogenoalkane?
  2. clownfish's Avatar
    • Benevolent Member
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    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by xXxiKillxXx)
    suggest why 1-chlorobutane reacts with water via a different mechanism.

    My book doesn't cover this at all, what exactly are we supposed to talk about?
    I checked the mark scheme, it says something about 1-chlorobutane being a primary halogenoalkane?
    Primary halogenoalkanes typically react by an Sn2 mechanism and Tertiary halogenalkanes typically react by an Sn1 mechanism.


    More information on here:
    http://www.docbrown.info/page06/OrgM...ALOGENOALKANES
  3. Ari Ben Canaan's Avatar
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    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by xXxiKillxXx)
    suggest why 1-chlorobutane reacts with water via a different mechanism.

    My book doesn't cover this at all, what exactly are we supposed to talk about?
    I checked the mark scheme, it says something about 1-chlorobutane being a primary halogenoalkane?
    A different mechanism with respect to WHAT ?

    Could you provide the full question ?
  4. Silkysam's Avatar
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    • Posts: 339
    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by xXxiKillxXx)
    suggest why 1-chlorobutane reacts with water via a different mechanism.

    My book doesn't cover this at all, what exactly are we supposed to talk about?
    I checked the mark scheme, it says something about 1-chlorobutane being a primary halogenoalkane?
    What are we comparing it to? Is it compared to a tertiary halogenoalkane, or to reacting with NaOH (or KOH) instead of water, etc?

    If it is the former then clownfish is right and it's due to the relative stabilities of the intermediate carbocations that would be produced.
  5. charco's Avatar
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    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by xXxiKillxXx)
    suggest why 1-chlorobutane reacts with water via a different mechanism.

    My book doesn't cover this at all, what exactly are we supposed to talk about?
    I checked the mark scheme, it says something about 1-chlorobutane being a primary halogenoalkane?
    OK here's a run through of nucleophilic substitution mechanisms.

  6. xXxiKillxXx's Avatar
    • Overlord in Training
    • Location: Trapped out in the Dunya
    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by Ari Ben Canaan)
    A different mechanism with respect to WHAT ?

    Could you provide the full question ?
    Here yougo:

    http://www.edexcel.com/migrationdocu...e_20090603.pdf

    Question 20, page 11-13.


    (Original post by Silkysam)
    What are we comparing it to? Is it compared to a tertiary halogenoalkane, or to reacting with NaOH (or KOH) instead of water, etc?

    If it is the former then clownfish is right and it's due to the relative stabilities of the intermediate carbocations that would be produced.
  7. xXxiKillxXx's Avatar
    • Overlord in Training
    • Location: Trapped out in the Dunya
    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by charco)
    OK here's a run through of nucleophilic substitution mechanisms.
    Thank you, I'll look through that now.
  8. xXxiKillxXx's Avatar
    • Overlord in Training
    • Location: Trapped out in the Dunya
    Re: suggest why 1-chlorobutane reacts with water via a different mechanism.
    (Original post by charco)
    OK here's a run through of nucleophilic substitution mechanisms.

    I looked through that, and I understand now! Thanks
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