Chemical Forums
Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: Firehchicken on January 12, 2018, 10:54:23 PM
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I understand that a strong nucleophile is also a strong base, but I am unable to understand why A) is the strongest base among the 4.
I am guessing it has something to do with the hybridisation but I cannot see exactly why A) is stronger compared to B).
Isn't the oxygen in B) sp3 hybridised whereas A) is sp2 hybridised, and therefore B) should be the stronger base?
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Although there is often a correlation between nucleophilicity and basicity, there are other factors that come into play. Nucleophilicity is a kinetic phenomenon; in other words a strong nuclephile is one that reacts quickly. Does that help?
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Although there is often a correlation between nucleophilicity and basicity, there are other factors that come into play. Nucleophilicity is a kinetic phenomenon; in other words a strong nuclephile is one that reacts quickly. Does that help?
Hmm so in other words compound B) is more stable than A)... but how?
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Ready nucleophillic attack requires sufficient electronegative character, as well as physical access to the recipient electrophile. Does this help?
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Ready nucleophillic attack requires sufficient electronegative character, as well as physical access to the recipient electrophile. Does this help?
So compound A) is less sterically hindered than compound B). Right.
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Although there is often a correlation between nucleophilicity and basicity, there are other factors that come into play. Nucleophilicity is a kinetic phenomenon; in other words a strong nuclephile is one that reacts quickly. Does that help?
Hmm so in other words compound B) is more stable than A)... but how?
I use the term "stability" when I am talking about thermodynamics. Your subsequent answer, steric hindrance, is correct.