Test #4 Reactions Flashcards
Hydrohalogenation: Identifier and key features
Has H-X as a reactant, Markovnikov. Rearrangements
Hydrohalogenation of alkynes
Has H-X as a reactant. If there’s excess, goes to alkane. Concerted. Markovnikov.
Acid-catalyzed hydration/etherification
H2O or RO as a reactant. Markovnikov, rearrangements.
Acid-catalyzed hydration/etherification of alkynes
Acid and Water as a reactant. Becomes an Enol then a Ketone. Concerted, Markovnikov.
Hydroboration-Oxidation
BH3 is your reactant. Concerted. Syn addition. Anti-Markovnikov.
Hydroboration-oxidation of alkynes
BH3 and H202 , OH as reactants. Enol to Ketone. Concerted, Anti Markovnikov. Syn addition.
Epoxidation of alkenes
RCO3H or MCPBA as reactants. Makes a tringle on a oxygen. Concerted, Syn addition.
Halogenation of alkenes.
X2 as a reactant. Stepwise but no rearrangements. Anti addition. Make a triangle then broken with SN2. No F2
Halogenation of alkynes.
X2 as a reactant. Anti addition, can stop after 1 or 2 rounds.
Halohydrin formation from alkenes
X2 with H20/ROH. Nucleophile in second step is H2O, ROH. Adds to more substituted carbon.
Alpha0halo ketones from alkynes.
X2 and H2O. Enol to Ketone.
Anti0dihydroxlation of alkenes
RCO3H is your reactant with Acid. 2 step process. Anti addition, stepwise, make oxygen triangle then acid comes to break it up.
Syn- Dihydroxlayion of alkenes
OsO4 +NaHSO3, H2O or Kmno4 and NaOH. Syn addition. Bond to oxygens then make go to OH Groups.
Acidic ring opening of epoxides
Starts with an epoxide, acid, and water. Creates a linear figure with OH groups on each end. Anti addition.
Basic ring opening of epoxides.
Start with an epoxide and react with a nucleophile, typically a base and H3O+. Makes a linear product with 2 OH groups. Anti addition. Nucleophile goes to less substituted carbon.
Ozonolysis
O# and (Ch3)2S as reactants. Cut it in half and tack on O= caps. Alkynes too, with an additional O bond.
Hydrogenation of alkenes
Reactants are Pt, PD, Rh, or Ni with H2. Syn addition. Happens with alkynes as well.
Partial hydrogenation of alkynes
Reactants are H2 with Pd/CaCO3 (Lindlars catalyst) or Li EtNH2, -78 and H3Cl (Dissolving metal) Syn and anti addition respectively. without touching alkene.
Cycloporponation of alkenes with diazomethane
Ch2N2 with heat or light. Makes a triangle with no oxygen. Syn addition. Br or Cl only. Stereochemistry possible.
Cycloproponation of alkenes with CHX3.
Reactants are CHX2 and NaOR. Make a triangle with X groups as a hat. Syn addition, Cl or Br only. Steriochemistry.
Generation of alkynide nucleophiles.
NH2 and then a chain with BR. Deprotonates the alkyne and attach it to the Br chain via SN2.
Free radical halogenation of alkanes
X2 with Light. X is Cl or Br. Br is highly selective. Taking an alkane and adding a X group the hard way.
Free radical bromination
NBS with Hv. Adding a br group without taking off the alkene. Major product determined by alkene stability.
Radical hydrobromination of alkenes
H-Br and RooR is added to an alkene. Anti Markovnikovs product. Bromination the hard way.
Free radical polymerization
Look for polymerization or the addition of just an alkene. Adding on till termination.
