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Organic chemistry

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SHastatahoe
Posts: 3414 - Karma: 19
I took my last semester of Ochem 4 semesters ago.  I am now taking biochem, and for review we need to determine which is more nucleophillic

R----O-
or
R-----OH




I cannot remember how to determine nucleophillic strength, I think it is based on the pKa, or basicity.

Thanks
Jan 28 2009 4:25PM
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freezed
Posts: 12973 - Karma: 500
generally, the more basic, the more nucleophilic.

R-OH will be more nucleophilic than R-O-R
Jan 28 2009 4:39PM
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bibs_skibum
Posts: 4462 - Karma: 449
fact
Jan 28 2009 5:11PM
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SHastatahoe
Posts: 3414 - Karma: 19
Its

R-----O(-)

with a negative charge on the oxygen, there is not a second R group, making it rather basic.


Jan 28 2009 5:13PM
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pmills
Posts: 7162 - Karma: 59
Click for larger image
Jan 28 2009 6:38PM
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TheButterHashira
Posts: 9691 - Karma: 1,702
I want to learn organic chemistry, but I just got done with basic highschool chemistry so I'm a noob when it comes to that.
Jan 28 2009 6:39PM
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SHastatahoe
Posts: 3414 - Karma: 19
haha, awesome. 
Jan 28 2009 8:24PM
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St.Steezy
Posts: 4228 - Karma: 20
I actually just laughed out loud.. my buddies just gave me shit.
Jan 28 2009 10:28PM
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quixotic
Posts: 6937 - Karma: 2,978
You should make some acid... thats the first thing I think of when it comes to organic chemistry haha
Jan 28 2009 10:44PM
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freezed
Posts: 12973 - Karma: 500
hahaha


to the OP, sorry, I misunderstood what you were asking. the deprotonated RO- will be more nucleophilic.
Jan 29 2009 2:42PM
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jib_kid_01
Posts: 248 - Karma: 10
anything with an -OH group is a terrible nucleophile.
Jan 29 2009 6:15PM
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jib_kid_01
Posts: 248 - Karma: 10
shit i was thinking leaving group -OH is a terrible leaving group for substitution reactions but it is a good nucleophile! sorry
Jan 29 2009 6:18PM
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