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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?
Reply 1
Avatar for clownfish
clownfish
10
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/OrgMechs2.htm#HALOGENOALKANES
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 ?
Reply 3
Avatar for Silkysam
Silkysam
9
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.
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.

[video="youtube_share;DPA9yDmjuQo"]http://youtu.be/DPA9yDmjuQo[/video]
Reply 5
Avatar for xXxiKillxXx
xXxiKillxXx
OP
14
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/migrationdocuments/QP%20GCE%20Curriculum%202000/June%202009/6CH02_01_que_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.
Reply 6
Avatar for xXxiKillxXx
xXxiKillxXx
OP
14
Original post by charco
OK here's a run through of nucleophilic substitution mechanisms.


Thank you, I'll look through that now.
Reply 7
Avatar for xXxiKillxXx
xXxiKillxXx
OP
14
Original post by charco
OK here's a run through of nucleophilic substitution mechanisms.

[video="youtube_share;DPA9yDmjuQo"]http://youtu.be/DPA9yDmjuQo[/video]

I looked through that, and I understand now! Thanks :smile:

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