Organic chemistry determing nucleophile strength

In summary, to determine the strength of a base as a nucleophile, you need to consider its basicity and the pKa value of its conjugate acid. Generally, weak bases are good nucleophiles, but there are other factors to consider. Knowing the common weak and strong bases can also help determine base strength.
  • #1
physstudent1
270
1
this isn't exactly an specific question but a general one. I know that weak bases make good nucleophiles but how do I determine what bases are the weakest, what is weak enough to be considered a "good nucleophile" I'm a little confused please help thanks a lot!
 
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  • #2
physstudent1 said:
this isn't exactly an specific question but a general one. I know that weak bases make good nucleophiles but how do I determine what bases are the weakest, what is weak enough to be considered a "good nucleophile" I'm a little confused please help thanks a lot!


In general the more basic an agent is the more nucleophilic , however there are other factors to consider besides basicity. Your teacher is probably not going to get specific , just know the common bases that are considered weak or strong.
 
  • #3
To determine base strength you need to look at the pKa value for the molecules conjugate acid (add an H+ to the molecule). If the conjugate acid has a low pKa (strong acid) then the original molecule is a weak base...and high pKa=strong base.
 

1. What is a nucleophile in organic chemistry?

A nucleophile is a chemical species that donates an electron pair to form a covalent bond with another atom or molecule. It is characterized by having a high electron density and a positive or partial positive charge.

2. How is nucleophilicity determined in organic chemistry?

Nucleophilicity is determined by several factors, including the charge and electronegativity of the nucleophile, the steric hindrance of the nucleophile, and the nature of the leaving group on the electrophile.

3. What is the relationship between nucleophilicity and basicity?

Nucleophilicity and basicity are related, but not the same. Basicity refers to the ability of a molecule to accept a proton, while nucleophilicity refers to the ability to donate an electron pair. Generally, a strong base is also a strong nucleophile, but there are exceptions to this rule.

4. How does solvent affect nucleophilicity?

The solvent can have a significant impact on nucleophilicity. A polar solvent can stabilize the nucleophile and make it more reactive, while a nonpolar solvent can hinder nucleophilicity by solvating the nucleophile and making it less available for a reaction.

5. What are some common nucleophiles in organic chemistry?

Some common nucleophiles in organic chemistry include halides (such as chloride and bromide), amines, alcohols, and thiols. These nucleophiles can vary in strength depending on their structure and the reaction conditions.

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