Emperor Sheev
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Hello there, I am a little bit confused as to whether an organic reaction involving (nucleophilic?) substation or elimination involves a nucleophile or a base. So what i need to know is how to distinguish between the two? as i tend to lose marks when it asks to identify in AQA AS level Chemistry Unit 2. Thanks in advance
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EierVonSatan
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A strong base is usually a good nucleophile, it's not one or the other.
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Emperor Sheev
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(Original post by EierVonSatan)
A strong base is usually a good nucleophile, it's not one or the other.
I understand what you are saying but there are questions that crop up such as: "What is the role of the hydroxide ion in the reaction?" and they except an answer like "it is a base" and they explicitly state that they do not accept nucleophile as an answer. Why is this?
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EierVonSatan
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(Original post by Jatyization)
I understand what you are saying but there are questions that crop up such as: "What is the role of the hydroxide ion in the reaction?" and they except an answer like "it is a base" and they explicitly state that they do not accept nucleophile as an answer. Why is this?
The question is asking about the role that the species is playing in a given reaction.

If it's an elimination of HCl from a haloalkane - then OH- is acting as a base (by removing a proton)

If it's a nucleophilic substituion of a haloalkane - then OH- is acting as a nucleophile

So it can act as either (determined by reaction conditions) and you have to decide which In reality the two are in competition and you get a bit of both, but with careful control one is much favoured over the other.
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Emperor Sheev
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(Original post by EierVonSatan)
The question is asking about the role that the species is playing in a given reaction.

If it's an elimination of HCl from a haloalkane - then OH- is acting as a base (by removing a proton)

If it's a nucleophilic substituion of a haloalkane - then OH- is acting as a nucleophile

So it can act as either (determined by reaction conditions) and you have to decide which In reality the two are in competition and you get a bit of both, but with careful control one is much favoured over the other.
Oh right! okay that makes it so much more clearer... Thanks i appreciate the help
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