Chapter 10

Question 1

A reaction involving ions as reactants, intermediates, or products; occur through the heterolysis of covalent bonds

Answer 1

Ionic reaction

Question 2

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

Answer 2

Heterolysis

Question 3

The cleavage of a covalent bond so that each fragment departs with one of the electrons of the covalent bond that joined them

Answer 3

Homolysis

Question 4

An uncharged chemical species that contains an unpaired electron

Answer 4

Radical (or free radical)

Question 5

A compound with an oxygen-oxygen single bond

Answer 5

Peroxide

Question 6

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

Answer 6

Hydrogen abstraction

Question 7

A reaction involving radicals. Homolysis of covalent bonds occurs in radical reactions

Answer 7

Radical reaction

Question 8

The enthalpy change that accompanies the homolytic cleavage of a covalent bond

Answer 8

Homolytic bond dissociation energy, DH*

Question 9

A reaction in which one group replaces another in a molecule

Answer 9

Substitution reaction

Question 10

Substitution of a hydrogen by a halogen through a radical reaction mechanism

Answer 10

Radical halogenation

Question 11

A reaction in which one or more chlorine atoms are introduced into a molecule

Answer 11

Chlorination

Question 12

A reaction in which one or more halogen atoms are introduced into a molecule

Answer 12

Halogenation

Question 13

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

Answer 13

Chain reaction

Question 14

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

Answer 14

Enantiotopic hydrogens

Question 15

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

Answer 15

Diastereotopic hydrogens

Question 16

An atom or group that is bonded to an sp3-hybridized carbon adjacent to an alkene double bond

Answer 16

Allylic group

Question 17

The location of a group that is bonded to an sp3-hybridized carbon adjacent to an alkene double bond

Answer 17

Allylic position

Question 18

The replacement of a group at an allylic position

Answer 18

Allylic substitution

Question 19

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

Answer 19

Allylic radical

Question 20

The location of a group that is bonded to an sp3-hybridized carbon adjacent to a benzene ring

Answer 20

Benzylic position

Question 21

An atom or group bonded to an sp3-hybridized carbon adjacent to a benzene ring

Answer 21

Benzylic group

Question 22

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

Answer 22

Benzylic radical

Question 23

A large molecule made up of many repeating subunits

Answer 23

Polymer

Question 24

A very large molecule

Answer 24

Macromolecule

Question 25

The simple starting compound from which a polymer is made

Answer 25

Monomer

Question 26

Reactions in which individual subunits (called monomers) are joined together to form long-chain macromolecules

Answer 26

Polymerizations

Question 27

Polymers (macromolecules with repeating units) formed by adding subunits (called monomers) repeatedly to form a chain

Answer 27

Chain-growth polymer

Question 28

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

Answer 28

Addition polymer

Question 29

The reaction of an organic compound with oxygen to form a hydroperoxide

Answer 29

Autoxidation