Chapter 8

Question 1

A Lewis acid, an electron-pair acceptor, an electron-seeking reagent

Answer 1

Electrophile

Question 2

A Lewis base, an electron-pair donor that seeks a positive center in a molecule

Answer 2

Nucleophile

Question 3

In the addition of HX to an alkene, the hydrogen atom adds to the carbon atom of the double bond that already has the greater number of hydrogen atoms

Answer 3

Markovnikov’s rule

Question 4

A reaction that yields only one (or a predominance of one) constitutional isomer as the product when two or more constitutional isomers are possible products

Answer 4

Regioselective reaction

Question 5

An addition reaction where the hydrogen atom of a reagent becomes bonded to an alkene or alkyne at the carbon having fewer hydrogen atoms initially

Answer 5

Anti-Markovnikov addition

Question 6

The addition of water to a molecule, such as the addition of water to an alkene to form an alcohol

Answer 6

Hydration

Question 7

A two-step process for adding the elements of water (H and OH) to a double bond in a Markovnikov orientation without rearrangements. An alkene reacts with mercuric acetate (or trifluoroacetate), forming a bridges mercurinium ion. Water preferentially attacks the more substituted side of the bridged ion, breaking the bridge and resulting, after loss of a proton, in an alcohol. Reduction with NaBH4 replaces the mercury group with a hydrogen atom, yielding the final product

Answer 7

Oxymercuration-demercuration

Question 8

The addition of -OH and -HgO2CR to a multiple bond

Answer 8

Oxymercuration

Question 9

Addition of the elements of water to an alkene or alkyne in a fashion opposite to Markovnikov’s rule, such that the hydrogen becomes bonded to the carbon that had fewer hydrogens initially

Answer 9

Anti-Markovnikov hydration

Question 10

The addition of a boron hydride (either BH3 or an alkylborane) to a multiple bond

Answer 10

Hydroboration

Question 11

An ion containing a positive bromine atom bonded to two carbon atoms

Answer 11

Bromonium ion

Question 12

An ion containing a positive halogen atom bonded to two carbon atoms

Answer 12

Halonium ion

Question 13

A reaction in which a particular stereoisomeric form of the reactant reacts in such a way that it leads to a specific stereoisomeric form of the product

Answer 13

Stereospecific reaction

Question 14

A compound bearing a halogen atom and a hydroxyl group on adjacent (vicinal) carbons

Answer 14

Halohydrin

Question 15

A compound bearing a bromine atom and a hydroxyl group on adjacent (vicinal) carbons

Answer 15

Bromohydrin

Question 16

A compound bearing a chlorine atom and a hydroxyl group on adjacent (vicinal) carbons

Answer 16

Chlorohydrin

Question 17

An uncharged species in which a carbon atom is divalent

Answer 17

Carbene

Question 18

The carbene with the formula :CH2

Answer 18

Methylene

Question 19

A cerbene-like species

Answer 19

Carbenoid

Question 20

The installation of hydroxyl groups on adjacent carbons, such as by the reaction of OsO4 or KMnO4 with an alkene

Answer 20

1,2-dihydroxylation

Question 21

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

Answer 21

Syn addition

Question 22

An oxidation reaction in which an alkene reacts to become a 1,2-diol (also called a glycol) with the newly bonded hydroxyl groups added to the same face of the alkene

Answer 22

Syn dihydroxylation

Question 23

A reaction in which the carbon-carbon double bond of an alkene or triple bond of an alkyne is both cleaved and oxidized, yielding components with carbon-oxygen double bonds

Answer 23

Oxidative cleavage

Question 24

The oxidative cleavage of a multiple bond using O3 (ozone)

Answer 24

Oxonolysis

Question 25

The fragments that result (on paper) from the “disconnection” of a bond. The actual reagent that will, in a synthetic step, provide the synthon is called the synthetic equivalent

Answer 25

Synthon

Question 26

A compound that functions as the equivalent of a molecular fragment needed in synthesis

Answer 26

Synthetic equivalent