Chapter 10 Flashcards
A reaction involving ions as reactants, intermediates, or products; occur through the heterolysis of covalent bonds
Ionic reaction
The cleavage of a covalent bond so that one fragment departs with both of the electrons of the covalent bond that joined them; normally produces positive and negative ions
Heterolysis
The cleavage of a covalent bond so that each fragment departs with one of the electrons of the covalent bond that joined them
Homolysis
An uncharged chemical species that contains an unpaired electron
Radical (or free radical)
A compound with an oxygen-oxygen single bond
Peroxide
The process by which a species with an unshared electron (a radical) removes a hydrogen atom from another species, breaking the bond to the hydrogen homolytically
Hydrogen abstraction
A reaction involving radicals. Homolysis of covalent bonds occurs in radical reactions
Radical reaction
The enthalpy change that accompanies the homolytic cleavage of a covalent bond
Homolytic bond dissociation energy, DH*
A reaction in which one group replaces another in a molecule
Substitution reaction
Substitution of a hydrogen by a halogen through a radical reaction mechanism
Radical halogenation
A reaction in which one or more chlorine atoms are introduced into a molecule
Chlorination
A reaction in which one or more halogen atoms are introduced into a molecule
Halogenation
A reaction that proceeds by a sequential, stepwise mechanism, in which each step generates the reactive intermediate that causes the next step to occur; have chain-initiation steps, chain-propagating steps, and chain-terminating steps
Chain reaction
If replacement of each of two hydrogens (or ligands) by the same group yields compounds that are enantiomers, the two hydrogen atoms (or ligands) are said to be enantiotopic
Enantiotopic hydrogens
If replacement of each of two hydrogens (or ligands) by the same group yields compounds that are diastereomers, the two hydrogen atoms (or ligands) are said to be diastereotopic
Diastereotopic hydrogens
An atom or group that is bonded to an sp3-hybridized carbon adjacent to an alkene double bond
Allylic group
The location of a group that is bonded to an sp3-hybridized carbon adjacent to an alkene double bond
Allylic position
The replacement of a group at an allylic position
Allylic substitution
The radical formally related to propene by removal of a hydrogen atom from its methyl group. The two contributing resonance structures of the delocalized radical each include an unpaired electron on a carbon adjacent to the double bond, such that a p orbital on each of the three carbons overlaps to delocalize the radical to each end of the allyl system, which the radical carbon is adjacent to a carbon-carbon double bond
Allylic radical
The location of a group that is bonded to an sp3-hybridized carbon adjacent to a benzene ring
Benzylic position
An atom or group bonded to an sp3-hybridized carbon adjacent to a benzene ring
Benzylic group
A radical where the unpaired electron is on a carbon bonded to a benzene ring. The unpaired electron is delocalized into the benzene ring through conjugation, resulting in a relatively stable radical
Benzylic radical
A large molecule made up of many repeating subunits
Polymer
A very large molecule
Macromolecule
The simple starting compound from which a polymer is made
Monomer
Reactions in which individual subunits (called monomers) are joined together to form long-chain macromolecules
Polymerizations
Polymers (macromolecules with repeating units) formed by adding subunits (called monomers) repeatedly to form a chain
Chain-growth polymer
A polymer that results from a stepwise addition of monomers to a chain (usually through a chain reaction) with no loss of other atoms or molecules in the process
Addition polymer
The reaction of an organic compound with oxygen to form a hydroperoxide
Autoxidation
