Ranking Nucleophiles: Understanding Reactivity and Polarizability

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In summary, nucleophilicity is the ability of a chemical species to donate a pair of electrons to form a new bond with an electrophilic atom or molecule. The strength of a nucleophile affects its reactivity, with stronger nucleophiles being more reactive in nucleophilic substitution reactions. Factors such as electronegativity, size, and solvent can influence the strength of a nucleophile. A strong nucleophile is highly reactive and has a greater ability to donate electrons, while a weak nucleophile is less reactive. The strength of a nucleophile can be determined experimentally through methods such as kinetic studies, competition reactions, and nucleophilic displacement reactions.
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AsuraSky
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One the practice problems i was doing in preparation for my exam was to rank the following nucleophiles in the order of decreasing reactivity, best nucleophile first.

Nucleophiles: CH3OH, Br-, NH3, F-, CH3S-

The answer was CH3S->Br->NH3>F->CH3OH

What I don't understand is why CH3S- is a stronger nucleophile than the bromide ion, shouldn't bromide be stronger because it's a bigger atom and thus have more polarizability?
 
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You sure it is a good row? It seems that amonia should be a better nucleophile than Br-?
 

FAQ: Ranking Nucleophiles: Understanding Reactivity and Polarizability

What is the definition of nucleophilicity?

Nucleophilicity is the ability of a chemical species to donate a pair of electrons to form a new bond with an electrophilic atom or molecule.

How does the strength of a nucleophile affect its reactivity?

The stronger the nucleophile, the more reactive it will be in nucleophilic substitution reactions. This is because a strong nucleophile has a greater ability to donate electrons and form a new bond with an electrophilic atom or molecule.

What factors influence the strength of a nucleophile?

The main factors that influence the strength of a nucleophile include the electronegativity of the atom or group, the size of the atom, and the solvent used in the reaction.

What is the difference between a strong nucleophile and a weak nucleophile?

A strong nucleophile is highly reactive and has a greater ability to donate electrons and form new bonds. A weak nucleophile, on the other hand, is less reactive and has a lower ability to donate electrons.

How can the strength of a nucleophile be determined experimentally?

The strength of a nucleophile can be determined experimentally through various methods such as kinetic studies, competition reactions, and nucleophilic displacement reactions. These methods allow for the comparison of different nucleophiles and their reactivity.

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