Chapter 7

Question 1

An old classification for a compound that is an alkene, stemming from “oil-forming gas”

Answer 1

Olefin

Question 2

Diastereomers that differ in their stereochemistry at adjacent atoms of a double bond or on different atoms of a ring; cis = same side and trans = opposite sides

Answer 2

Cis-trans isomers

Question 3

A system for designating the stereochemistry of alkene diastereomers based on the properties of groups in the Cahn-Ingold-Prelog convention. An E isomer has the highest priority groups on opposite sides of the double bond, a Z isomer has the highest priority groups on the same side of the double bond

Answer 3

(E)-(Z) system

Question 4

A reaction in which hydrogen adds to a double or triple bond; is often accomplished through the use of a metal catalyst, such as platinum, palladium, rhodium, or ruthenium

Answer 4

Hydrogenation

Question 5

The standard enthlapy change that accompanies the hydrogenation of 1 mol of a compound to form a particular product

Answer 5

Heat of hydrogenation

Question 6

A reaction that results in the loss of two groups from the substrate and the formation of a π bond. The most common elimination reaction is a 1,2 elimination or β elimination, in which two groups are lost from adjacent atoms

Answer 6

Elimination reaction

Question 7

An elimination reaction that results in the loss of HX from adjacent carbons of the substrate and the formation of a π bond

Answer 7

Dehydrohalogenation

Question 8

A bimolecular 1,2 elimination in which, in a single step, a base removes a proton and a leaving group departs from the substrate, resulting in the formation of a π bond

Answer 8

E2 reaction

Question 9

A unimolecular elimination in which, a slow, rate-determining step, a leaving group departs from the substrate to form a carbocation. The carbocation then, in a fast step, loses a proton with the resulting formation of a π bond

Answer 9

E1 reaction

Question 10

A rule stating that an elimination will give as the major product the most stable alkene (i.e., the alkene with the most highly substituted double bond)

Answer 10

Zaitsev’s rule

Question 11

A principle stating that when the ratio of products of a reaction is determined by relative rates of a reaction, the most abundant product will be the one that is formed the fastest

Answer 11

Kinetic (or rate) control

Question 12

When an elimination yields the alkene with the less substituted double bond

Answer 12

Hofmann rule

Question 13

A confirmation in which Vicinal groups lie in the same plane

Answer 13

Coplanar

Question 14

The relative position of two groups that have a 180* dihedral angle between them

Answer 14

Anti coplanar

Question 15

The relative position of two groups that have a 0* dihedral angle between them

Answer 15

Syn coplanar

Question 16

An elimination that involves the loss of a molecule of water from the substrate

Answer 16

Dehydration

Question 17

A reaction that results in a product with the same atoms present but a different carbon skeleton from the reactants. A 1,2 shift is a rearrangement that involves the migration of a group (with its electrons) from one atom to the atom next to it

Answer 17

Rearrangement

Question 18

A methyl anion, -:CH3, or methyl species that reacts as though it were a methyl anion

Answer 18

Methanide

Question 19

The migration of a chemical bond with its attached group from one atom to an adjacent atom

Answer 19

1,2 shift

Question 20

An alkyl anion, R:-, or alkyl species that reacts as though it were an alkyl anion

Answer 20

Alkanide

Question 21

A hydrogen anion, H:-, or a species that reacts as though it were a hydride anion. Hydrogen with a filled 1s shell (containing two electrons) and negative charge

Answer 21

Hydride

Question 22

A hydrogen atom attached to a carbon atom that is bonded to another carbon atom by a triple bond

Answer 22

Acetylenic hydrogen atom

Question 23

A general term for a molecule having halogen atoms bonded to each of two adjacent carbons

Answer 23

Vicinal dihalides (vic-dihalide)

Question 24

When two identical groups are bonded to the same carbon

Answer 24

Geminal

Question 25

A general term for a molecule or group containing two halogen atoms bonded to the same carbon

Answer 25

Geminal dihalide (gem-dihalide)

Question 26

The introduction of an alkyl group into a molecule

Answer 26

Alkylation

Question 27

Catalytic reaction in which the catalyst is insoluble in the reaction mixture

Answer 27

Heterogeneous catalysis

Question 28

Catalytic reactions in which the catalyst is soluble in the reaction mixture

Answer 28

Homogeneous catalysis

Question 29

A compound that doesn’t contain any multiple bonds

Answer 29

Saturated compound

Question 30

A compound that contains one or more double bonds

Answer 30

Unsaturated compound

Question 31

An addition that places both parts of the adding reagent on the same face of the reactant

Answer 31

Syn addition

Question 32

An addition that places the parts of the adding reagent on opposite faces of the reactant

Answer 32

Anti addition

Question 33

Metallic palladium deposited on calcium carbonate

Answer 33

Lindlar’s catalyst

Question 34

A method for planning syntheses that involves reasoning backward from the target molecule through various levels of precursors and thus finally to the starting materials

Answer 34

Retrosynthetic analysis