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Author Topic: Why is A) the best nucleophile?  (Read 701 times)

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Firehchicken

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Why is A) the best nucleophile?
« on: January 12, 2018, 04:54:23 PM »

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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Babcock_Hall

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Re: Why is A) the best nucleophile?
« Reply #1 on: January 13, 2018, 06:21:22 AM »

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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Firehchicken

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Re: Why is A) the best nucleophile?
« Reply #2 on: January 13, 2018, 06:14:00 PM »

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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NateDogg

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Re: Why is A) the best nucleophile?
« Reply #3 on: January 13, 2018, 06:49:20 PM »

Ready nucleophillic attack requires sufficient electronegative character, as well as physical access to the recipient electrophile. Does this help?
« Last Edit: January 13, 2018, 07:03:57 PM by NateDogg »
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Firehchicken

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Re: Why is A) the best nucleophile?
« Reply #4 on: January 14, 2018, 01:11:46 AM »

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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Babcock_Hall

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Re: Why is A) the best nucleophile?
« Reply #5 on: January 14, 2018, 04:43:55 AM »

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.
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