Chapter 8 Flashcards
A Lewis acid, an electron-pair acceptor, an electron-seeking reagent
Electrophile
A Lewis base, an electron-pair donor that seeks a positive center in a molecule
Nucleophile
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
Markovnikov’s rule
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
Regioselective reaction
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
Anti-Markovnikov addition
The addition of water to a molecule, such as the addition of water to an alkene to form an alcohol
Hydration
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
Oxymercuration-demercuration
The addition of -OH and -HgO2CR to a multiple bond
Oxymercuration
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
Anti-Markovnikov hydration
The addition of a boron hydride (either BH3 or an alkylborane) to a multiple bond
Hydroboration
An ion containing a positive bromine atom bonded to two carbon atoms
Bromonium ion
An ion containing a positive halogen atom bonded to two carbon atoms
Halonium ion
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
Stereospecific reaction
A compound bearing a halogen atom and a hydroxyl group on adjacent (vicinal) carbons
Halohydrin
A compound bearing a bromine atom and a hydroxyl group on adjacent (vicinal) carbons
Bromohydrin
A compound bearing a chlorine atom and a hydroxyl group on adjacent (vicinal) carbons
Chlorohydrin
An uncharged species in which a carbon atom is divalent
Carbene
The carbene with the formula :CH2
Methylene
A cerbene-like species
Carbenoid
The installation of hydroxyl groups on adjacent carbons, such as by the reaction of OsO4 or KMnO4 with an alkene
1,2-dihydroxylation
An addition that places both parts of the adding reagent on the same face of the reactant
Syn addition
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
Syn dihydroxylation
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
Oxidative cleavage
The oxidative cleavage of a multiple bond using O3 (ozone)
Oxonolysis
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
Synthon
A compound that functions as the equivalent of a molecular fragment needed in synthesis
Synthetic equivalent
