Analyzing Organic Reactions

type of acid or base: electron acceptor (in formation of a covalent bond), vacant p-orbitals or positively polarized atoms; tend to be electrophiles

type of acid or base: electron donor (in formation of a covalent bond), lone pair of electrons that can be donated, are often anions; tend to be nuclephiles

created by interaction of Lewis acid and base

type of acid or base: can donate a proton (H+)

type of acid or base: can accept a proton (H+)

molecule that can act as either a Bronsted-Lowry acid or base (like H2O)

measures strength of acid in solution

acid dissociation constant (Ka)

pKa

“nucleus-loving” species; has lone pairs or π bonds that can form new bonds to electrophiles; strength is based on relative rates of reaction with common electrophile

four major factors that determine nucleophilicity:

“electron-loving” species; has positive charge or positively polarized atom than can accept an electron pair forming new bonds with a nucleophile; more positive compounds are more electrophilic

a bond is broken and both electrons are given to one of the two products; essentially the opposite of a coordinate covalent polar bond formation

molecular fragments that retain electrons after heterolysis; best groups will be able to stabalize extra electrons: weak bases (like I-, Br-, and Cl-) are good, H ions and alkanes are very bad

a reaction where a nucleophile forms a bond with a substrate carbon and a leaving group leaves

type of nucleophilic substitution reaction: two steps: first, leaving group leaves forming carbocation, second, nucleophile attacks carbocation from either side; reactions prefer more substituted carbons because alkyl group can donate electron density and stabilize carbocation; rate depends on concentration of substrate

type of nucleophilic substitution reaction: one step: nucleophile attacks from back (less sterics) as leaving group leaves; inversion of stereochemistry; reaction prefers less substituted carbons because less steric hindrance; rate depends on concentration of substrate and nucleophile

hypothetical charge an atom would have if all of its bonds were totally ionic; can be calculated from molecular formula

most reduced form of carbon

most oxidized form of carbon

oxidation state of ions

an increase in oxidation state assisted by oxidizing agents

accept electrons and are reduced in process; have affinity for electrons or unusually high oxidation state, often contain metal and large number of oxygens

common oxidizing agent(s)