Chapter 7 Notecards

a system for designating the stereochemistry of alkene diastereomers based on the priorities 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.

the migration of a chemical bond with its attached group from one atom to an adjacent atoms.

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

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

the introduction of alkyl group into a molecule

in addition that places the parts of the adding reagent on opposite faces of the reactants.

the relative position of two groups that have 180° dihedral angle between them

Diastereomers that differ in their stereochemistry at adjacent atoms of a double bond or on different atoms of the ring. Cis groups are on the same side of a double bond or ring. Trans groups are on opposite sides of a double bond or ring.

a confirmation in which vicinal groups lie in the same plane

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

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

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

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

substituents that are on the same atom.

the standard enthalpy change that accompanies the hydrogenation of one mole of a compound to form a particular product

catalytic reactions in which the catalyst is insoluble in the reaction mixture

one and elimination use the alkene with the less substituted double bond, it is said to follow the Hoffman rule

catalytic reactions in which the catalyst is soluble in the reaction mixture.

a hydrogen anion, H:– hydrogen with a filled 1s shell (containing two electrons) and negative charge.

a reaction in which hydrogen adds to a double or triple bond. This is often accomplished to the use of a metal catalyst such as platinum, Palladium, rhodium, or ruthenium.

a principal stating that when the ratio products of reaction is determined by relative rates of reaction, the most abundant product will be to one that is formed fastest. Also called rate control.

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

an old name for an alkene

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

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.

a compound that does not contain any multiple bonds.

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

the relative position of two groups that have a 0° dihedral angle between them.

a compound that contains multiple bonds.

a general term for a molecule having halogen atoms bonded to each other to adjacent carbons

a rule stating that and elimination will give as the major product the most stable alkene (i.e., the alkene with the most highly substitutive double bond).