Ranking Nucleophiles: Understanding Reactivity and Polarizability

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SUMMARY

The discussion centers on ranking nucleophiles based on their reactivity, specifically analyzing the order: CH3S- > Br- > NH3 > F- > CH3OH. The key takeaway is that CH3S- is a stronger nucleophile than Br- due to its higher charge density and ability to donate electrons more readily, despite Br- being larger and more polarizable. The misconception that larger size correlates with nucleophilicity is clarified, emphasizing that charge and electronegativity play critical roles in determining nucleophile strength.

PREREQUISITES
  • Understanding of nucleophilicity and electrophilicity
  • Familiarity with polarizability concepts in chemistry
  • Knowledge of the properties of common nucleophiles such as CH3S-, Br-, NH3, F-, and CH3OH
  • Basic grasp of Lewis structures and electron donation
NEXT STEPS
  • Study the factors affecting nucleophilicity in organic chemistry
  • Learn about the role of charge density in determining nucleophile strength
  • Investigate the relationship between atomic size and polarizability
  • Explore examples of nucleophilic substitution reactions and their mechanisms
USEFUL FOR

Chemistry students, organic chemists, and anyone preparing for exams involving nucleophiles and reaction mechanisms will benefit from this discussion.

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-?
 

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