substitution reaction
a reaction in which a reagent atom or molecule takes the place of another atom/group in a reactant molecule
reagent
reactant necessary to make the primary reactant give the desired product
byproduct
any product other than the primary product for which the reaction is carried out for commercial reasons
halogenation
a substitution reaction in which an alkane takes on at least one halogen atom
bromination
halogenation with bromine
chlorination
halogenation with chlorine
addition reaction
reactions in which a reagent is taken into the structure of the a primary reactant, producing only one product and no byproduct
hydrogenation
addition of H? to an alkene/alkyne or to an molecule with carbon-carbon multiple bonds
saturated hydrocarbons
hydrocarbons in which all carbon-carbon bonds are single (i.e. alkanes)
unsaturated hydrocarbons
hydrocarbons with at least one carbon-carbon multiple bond (i.e. alkenes or alkynes)
polyunsaturated hydrocarbons
hydrocarbons with more than one carbon-carbon multiple bond (e.g. dienes)
Lindler's catalyst
a proprietary form of Pd (palladium) catalyst used for the restricted hydrogenation of alkynes
hydration
addition of water to an alkene or other unsaturated molecule; no byproducts
symmetrical alkene
an alkene with bilateral symmetry
unsymmetrical alkene
an alkene without bilateral symmetry
symmetrical reagent
a reagent which splits into two identical portions (usually ions) in an addition reaction
unsymmetrical reagent
a reagent which splits into two different portions in an additions reaction
Markonikov's rule
in an alkene addition with unsymmetrical alkene and reagent, the actual product will be the one in which the electroposition portion (usually H?) of reagent adds to the carbon of the double bond with the most hydrogens
Markonikov product
the product actually occurring in alkene addition in accordance with Markonikov's rule
anti-Markonikov product
a hypothetically possible product in alkenes addition which is not predicted by Markonikov's rule
regioisomers
the two possible products of unsymmetrical alkyne addition reaction
electrophilic reagent
a reagent with poles of a positive and negative charge
1,2-addition product
the Markonikov product of stoichiometrically limited electrophilic reagent to 1,3-butadiene
1,4-addition product
the non-Markonikov product of stoichiometrically limited electrophilic reagent to 1,3-butadiene
cycloaddition
a type of 1,4-addition in which the reagent has a double bond resulting in a cyclic product
aromatic compound
any compound containing a benzene ring
ortho
two side groups on adjacent carbons
meta
two side groups separated by a ring carbon with no substituent
para
two side groups on opposite sides of a benzene ring
aryl side group
a substituent containing a benzene ring; symbol Ar
arenes
aromatic hydrocarbons
reaction mechanism
a series of steps of "elementary reactions" resulting in the overall reaction observed macroscopically
elementary reaction
a single reaction in a reaction mechanism
electrophilic attraction
attraction between a species (ion or molecule) and electrons
electrophile
a species capable of attracting electrons
electrophilic substitution
a substitution reaction occurring because of electrophilic attraction between electrons in a reactant and an electrohpilic reagent
directed substitution
when synthesizing a disubstituted benezene derivative, the action of the first substituent in determining the relative position of the second
ortho-/para-directing group
a benzene substituent which directs a second substituent to either an ortho- or para-position
meta-directing group
a benzene substituent which directs a second substituent to a meta-position
ortho-/para- directing groups
-NH?, -NHR, NR? (amino and derivatives)
-OH, -OR (hydroxy and derivatives)
-R (alkyls)
-NHC(=O)R (acylamino)
-X (halides)
meta-directing
-NO? (nitro)
-CN (cyano)
-SO?OH (sulfonic acid)
-COOH, -COOR, -COR (carboxy and derivatives)
-C(=O)NH? (carboxyamido)
activating groups
benzene substituents which increase the reactivity of a benzene ring; includes ortho-/para-directing groups except halogens
deactivating groups
benzene substituents which decrease the reactivity of a benzene ring; includes meta-directing groups plus halogens
polycyclic aromatic hydrocarbon
a hydrocarbon with two or more fused benzene rings; abbreviated PAH
fused ring system
a compound with two or more rings joined side-to-side
naphthalene
C??H? (white)
anthracene
C??H?? (light green)
pyrene
C??H?? (yellow)
graphite
C:H = ?