NucElec - Nucleophiles Electrophiles and Leaving Groups Nucleophiles Translation Nucleus-loving Chemical meaning Reacts with positivelycharged(or

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Nucleophiles, Electrophiles and Leaving Groups
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Nucleophiles • Translation: Nucleus-loving • Chemical meaning: Reacts with positively- charged (or partially positive) atoms (electrophiles: electron-loving) • Characteristics: Nucleophilic atoms will have either lone pairs or pi bonds that can be used to form new bonds to electrophiles
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Nucleophile Examples Anions Pi bonds Atoms with lone pairs Br C C H H H H H O H OH C N C C H H C C C C C C H H H H H H N H H H O C H 3 C CH 3
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Br H O H OH Br H Relative Nucleophile Strength - Charge • Given two nucleophiles with the same nucleophilic atom, a negative charge makes the atom more reactive • In more general terms, the stronger base is the stronger nucleophile (given the same nucleophilic atom) is a better nucleophile than is a better nucleophile than
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Relative Nucleophile Strength - Solvent • Hydrogen-bonding solvents (protic solvents) reduce nucleophilicity by interacting with the free electrons in the nucleophile • This effect is particularly strong for small atoms with concentrated charges, thus larger atoms are more nucleophilic in protic solvents (~opposite basicity) HS - > HO - I - > Br - > Cl - > F - O H H N H H H O H H O H H O H H
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This note was uploaded on 10/09/2011 for the course BCH BCH4101 taught by Professor Dr.sener during the Spring '11 term at University of Ottawa.

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NucElec - Nucleophiles Electrophiles and Leaving Groups Nucleophiles Translation Nucleus-loving Chemical meaning Reacts with positivelycharged(or

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