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document Nucleophilic Substitution Reactions
Nucleophilic substitution reactions are an important class of reactions that allow the interconversion of functional groups.  The general scheme can be seen below, however the mechanism (electron pathway) is dependent upon the structure of the starting material and nucleophile.  A wide...
01 Aug, 2011 Comments: 0
document Thermodynamics of Nucleophilic Substitutions
Multi-step reactions have intermediates (I) and multiple transition states (TS). Remember, a transition state is the theoretical energy maxima where bonds are being made and broken, usually shown by dashed lines in Lewis structures.  An intermediate, though not the final product, is typically...
07 Mar, 2011 Comments: 0
document SN2 Mechanism of Nucleophilic Substitution
SN2 indicates a substitution, nucleophilic, bimolecular reaction, described by the kinetic expression: rate = k [Nu][R-LG].  The transition state in the rate determining step involves both the nucleophile and molecule with the leaving group.   This pathway is a concerted...
22 Jul, 2011 Comments: 0
document SN1 Mechanism of Nucleophilic Substitution
SN1 indicates a substitution, nucleophilic, unimolecular reaction, described by the kinetic expression: rate = k [R-LG].  This means, the concentration of the nucleophile is not significant in increasing the reaction rate because it is not a part of the rate determining step. ...
22 Jul, 2011 Comments: 0
document Nucleophilicity versus Basicity
Nucleophilicity and basicity are very similar properties in that species that are nucleophiles are usually also bases (e.g. HO- , RO-).  However, some nucleophiles are poor bases and some bases are poor nucleophiles.  Bases are predominantly defined by the pKa of...
16 Aug, 2012 Comments: 0
document Leaving Groups
 A leaving group , LG, is an atom (or a group of atoms) that is displaced as stable species taking with it the electrons in the bond that were connecting it to the rest of the molecule. Typically the leaving group is an anion (e.g. Cl-) or a neutral molecule...
13 May, 2012 Comments: 0
document Solvent Effects
In general terms, the choice of solvent can have a significant effect on the performance of a reaction. Factors to considering when choosing a solvent for a specific reaction are: solubility : need to get reagents in the same phase, the molecules need to collide to react ...
11 May, 2012 Comments: 0
document Nucleophile
Nucleophile means "nucleus-loving" which describes the tendency of an electron rich species/compound to be attracted to the positive charge of an electron poor species/compound, the electrophile.  Electrons naturally flow from areas of high electron density (nucleophilic areas) to areas of...
11 May, 2012 Comments: 0

Department of Chemistry & Chemical Biology