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WGU-Organic Chem 11
Reactions, Part 1
| Question | Answer |
|---|---|
| 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 |
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