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WGU-Organic Chem 11

Reactions, Part 1

reaction mechanism the step by step sequence of elementary reactions by which overall chemical change occurs
energy diagram shows the changes in energy in a reaction from reactants to products
reaction coordinate energy is measured along the vertical axis and the change in position of the atoms during a reaction is measured on the horizontal axis
heat of reaction the difference in energy between the reactants and products
exothermic heat is released when the energy of the products is lower than the energy of the reactants
endothermic heat is absorbed when the energy of the products is higher than the energy of the reactants
transition state the point on the reaction coordinate at which the the energy is at maximum at this point energy is released and products are made
reaction intermediate corresponds to an energy minimum between two transition states
activation energy difference in energy between the reactants and the transition state or the minimum energy required for a reaction to occur
rate-determining step the slowest step in a multistep reaction or the step the crosses the highest energy barrier
Chemical Reaction A transformation resulting in a change of composition, constitution and/or configuration of a compound
Reactant or Substrate The organic compound undergoing change in a chemical reaction.
Reagent A common partner of the reactant in many chemical reactions. It may be organic or inorganic; small or large; gas, liquid or solid
Product(s) The final form taken by the major reactant(s) of a reaction.
Reaction Conditions The environmental conditions, such as temperature, pressure, catalysts & solvent, under which a reaction progresses optimally. Catalysts
four reactions classes by structural change addition, substitution, elimination, and rearrangement
reactions classes by reaction type Acid Base reaction and Oxidation Reduction reaction
Brønsted theory an acid is a proton donor, and a base is a proton acceptor
The stronger the acid the weaker its conjugate base
the stronger the base the weaker its conjugate acid
Acid-base equilibria always favor the weakest acid and the weakest base
Lewis theory an acid is an electron pair acceptor, and a base is an electron pair donor.
Carbocations Lewis acids and some are Bronsted acids as well
Electrophile Lewis Acid or An electron deficient atom, ion or molecule that has an affinity for an electron pair, and will bond to a base or nucleophile.
Nucleophile Lewis Base or An atom, ion or molecule that has an electron pair that may be donated in bonding to an electrophile (or Lewis acid).
Reduced If the number of hydrogen atoms bonded to a carbon increases, and/or if the number of bonds to more electronegative atoms decreases, the carbon in question has been reduced (i.e. it is in a lower oxidation state).
Oxidized If the number of hydrogen atoms bonded to a carbon decreases, and/or if the number of bonds to more electronegative atoms increases, the carbon in question has been oxidized (i.e. it is in a higher oxidation state).
Reactions of Alkanes C–C,C–H Substitution of H(Cl,Br)and Combustion (CO2 & H2O)
Reactions of Alkenes C=C–C–H Addition and Substitution of H
Alkynes C≡C–H Addition and Substitution of H
Alkyl Halides H–C–C–X Substitution of X and Elimination of HX
Alcohols H–C–C–O–H Substitution of H,Substitution of OH,Elimination of HOH, Oxidation or elimination of 2H
Ethers (α)C–O–R Substitution of OR or Substitution of α–H
Amines C–NRH Substitution of H;Addition to N; Oxidation of N
Benzene Ring C6H6 Substitution of H
Aldehydes (α)C–CH=O Addition or Substitution of H or α–H
Ketones (α)C–CR=O Addition or Substitution of α–H
Carboxylic Acids (α)C–COOH Substitution of H; Substitution of OH,Substitution of α–H; and Addition to C=O
Carboxylic Derivatives (α)C–CZ=O(Z = OR, Cl, NHR, etc.) Substitution of Z; Substitution of α–H, and Addition to C=O
variables of organic reactions reactant structure, reagent characteristics, regioselectivity, stereoselectivity, stereospecificity, reaction rates, reaction intermediates,energetics, electronic effects, steric effects, stereoelectronic effects, and solvent effects
carbocation R3C+
carbanion R3C:-
radical R3C.
carbene R2C:
Most important alkane reaction combustion
electrophilic addition reaction of alkene three types: hydrogen halide addition, addition of water, and addition of halogens
Markovnikov's rule for addition of hydrohalides to alkenes in the addition of HX to an alkene; hydrogen adds to the double bonded carbon that has the most hydrogens already bonded to it
Markovnikov's rule for addition of water to alkenes in an acid-catalyzed hydration; H adds to the double bonded carbon with the most H's where OH bonds to the carbon with the least H's
addition of Cl2 or Br2 to cyclohexene yields with CH2Cl2 generates a trans-1,2 dibromo(chloro)cyclohexane which is highly stereoselective in that Halogen atoms always add trans to each other
oxidation of alkenes Osmium tetroxide(OsO4)creates a cis cyclic osmate with NaHSO3 and water creates a cis glycol(two alcohols at double bond in cis formation) or osmium reoxidized with H2O2 instead of reduced with NaHSO3
reduction of alkenes Hydrogenation(H2)with a transition metal catalyst Platinum, palladium, ruthenium, and nickel to give an alkane at 25 degrees celsius and 3 atm pressure by syn addition of Hydrogens in cis formation stereoselectively
applications of ethylene the simplest alkene polymerization to make plastics, oxidation to make antifreeze, alkylation to make polystyrene insulation,itself used as anesthetic agen, fruit ripener, and welding gas
most common alkene reaction addition reaction of HCl, HBr, H2O,Br2, and Cl2
Addition of HX to alkene yields haloalkane regioselectively and follows Markovnikov's rule occurs in two steps with carbocation intermediate
Acid(H2SO4)-Catalyzed Hydration(H2O) of alkene yields alcohol hydration is regioselective and follows Markovnikov's rule two step reaction with carbocation intermediate
Addition of Bromine(Br2)/Chlorine(Cl2)to alkene in CH2Cl2 yields trans configuration of dihalide alkane in two steps by anti addition of a bridged bromonium/chloronium ion intermediate
Oxidation(OsO4)of alkene with ROOH yields glycols(cis diols) by the syn addition addition of -OH groups to the double bond via a cyclic osmate
Reduction(H2)of alkene with transition metal catalyst yields alkane predominantly using the syn addition of hydrogen
Nucleophilic Aliphatic Substitution(SN2)reactions of haloalkanes Occurs in one step where both nucleophile and leaving group are involved in transition state of the rate-determining step
SN2 of haloalkanes nucleophile may be negatively charged or neutral, results in an inversion of configuration at the reaction center, accelerated by polar aprotic solvents,and governed by degree of crowding around the site of reaction
Nucleophilic Aliphatic Substitution(SN1)of haloalkanes occurs in two steps where step 1 is slow, rate determining ionization of the C-X bond to form carbocation intermediate, followed by rapid reaction with nucleophile to complete substitution
SN1 of haloalkanes reaction at stereocenter gives racemic product and governed by electronic factors of the relative stability of the carbocation intermediate
SN1 of haloalkanes with alcohol yields ether
Beta-Elimination(E1)reaction of haloalkanes elimination of atoms or groups of atoms from adjacent carbons in two steps with the formation of a carbocation intermediate
E1 reaction of haloalkane with CH3COOH yields alkene and HX
Beta-Elimination(E2)of haloalkanes one step reaction with reaction of base to remove hydrogen, form the alkene, departure of leaving group all occurring together
E2 haloalkane with CH3O-Na+ and CH3OH yields two types of alkenes in varying persentages with the most stable the greater percentage
Created by: elainero