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69 Cards in this Set
- Front
- Back
Thermal Cracking
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Occurs when high temperatures cause homolytic breaking of C-C and C-H bonds.
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Homolytic Breaking
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Each of the 2 product fragments leaves with 1 bonding electron from the 1 reactant.
Aka. symmetrical processes A type of radical reaction. |
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Homolytic Bonding
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When 1 electron from each of the 2 reactants are donated to a newly-formed product.
Aka. symmetrical processes A type of radical reaction. |
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Heterolytic Breaking
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1 of the 2 product fragments leaves with both bonding electrons from the reactant.
Aka. unsymmetrical processes A type of polar reaction. |
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Heterolytic Bonding
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Where both electrons from 1 of the 2 reactants are donated to a newly-formed product.
Aka. unsymmetrical processes A type of polar reaction. |
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3 Steps of a simple Radical Substitution Reaction
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1. Initiation - free radical is produced
2. Propagation - carries on chain reaction 3. Termination - 2 radicals react together to form a stable product |
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Carbon is always _____________ly polarized, except when bonded to a metal.
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positive
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Nucleophile Examples
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ammonia, water, hydroxide, chloride ion
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Electrophile Examples
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acids, alkyl halides, carbonyl compounds
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Electrons move from a(n) _______philic source to a(n)_______philic source.
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nucleo to electro
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When ∆G° is negative, the reaction is _____________.
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spontaneous
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Formula for the relationship between K, e, ∆G°, and RT
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K=e ^ -∆G°/RT
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Bond Dissociation Energy (D)
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Energy needed to break a bond homolytically to produce 2 radical fragments.
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Solvation
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Clustering of solvent molecules around a solute particle to stabilize it.
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Solvent
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Dissolves the solute. Is in greater quantity than the solute.
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Exergonic Reaction
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Product has lower energy level than reactant.
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Endergonic Reaction
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Product has higher energy level than reactant.
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Formula for a Saturated Alkane
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Common names for Ethene and Propene
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Ethylene and Propylene
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Bond lengths in alkanes, alkenes, and alkynes
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154pm, 134pm, 120pm
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Bond angles in alkanes, alkenes, and alkynes
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109°, 120°, and 180°
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Why isn't rotation possible about a carbon-carbon double bond?
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π bond must break, then reform, costing 350kJ/mol
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Cahn-Ingold Prelog rules (sequence rules)
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Rules for assigning priorities to substituents or alkenes.
Aka. The E, Z designation |
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Heat of Hydrogenation (∆H°hydrog)
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Amount of heat released when a carbon-carbon double bond is hydrogenated.
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Electrophilic Addition Reaction
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Addition of an electrophile to a carbon-carbon double bond.
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Markovnikov's Rule
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In addition reactions, the H attaches to the C with fewer alkyl substituents.
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Hyperconjugation
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Stabilizing interaction between vacant p orbitals in a carbocation and C-H sigma bonds.
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Inductive Effects
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The electron-attracting or electron-withdrawing effect transmitted through sigma bonds. Occurs because of electronegativities of nearby atoms.
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Hammond Postulate
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The structure of a transition state resembles the structure of the nearest stable species.
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Transition State
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Highest energy point on a reaction curve.
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Dehydration
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Loss of water from an alcohol. Type of elimination reaction.
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Dehydrogenation
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Loss of HX from an alkyl halide. Type of elimination reaction.
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Halogenation reactions.
They occur on a cycloalkane, form only the ___________stereoisomer. |
Halogens add rapidly to alkene to yield 1,2-dihalides.
trans |
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Syn Addition Reaction
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2 ends of double bond react from same side.
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Syn Elimination Reaction
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2 groups leave from the same side.
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Anti Addition Reaction
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2 ends of double bond react from different sides.
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Anti Elimination Reaction
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2 groups leave from opposite sides.
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Halohydrin
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A 1,2-disubstituted haloalcohol.
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Bromohydrin
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A 1,2-disubstituted bromoalcohol.
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NBS
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N-bromosuccinimide decomposes in water to form Br2.
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Hydration
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Addition of water to a molecule.
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Oxymercuration
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Method for double-bond hydration using mercuric acetate as the reagent.
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Abbreviation for mercuric acetate.
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Hg(OAc)2
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THF
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Tetrahydrofuran.
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Hydrogen Peroxide
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H202
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Mercury (II) Acetate
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Hg(OAc)2
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Sodium Borohydride
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NaBH4
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Methylene, Vinyl, and Allyl groups.l
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CH2, CH=CH2, and CH2-CH=CH2
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Hydroboration-Oxidation Reaction
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HYDROBORATION: Alkene + borane (BH3) to yield an organoborane intermediate (RBH2).
OXIDATION: Organoborane (RBH2) + hydrogen peroxide (H2O2) to yield an alcohol. |
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Deuterium (D)
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Isotope of hydrogen consisting of 1 proton, 1 neutron, and 1 electron.
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Oxymercuration Reaction
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Alkene + mercury(II) acetate to yield an organomercury compound, then addition of sodium borohydride (NaBH4) to yield an alcohol.
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Carbene
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-R2C
-Neutral -Divalent C atom -6 electrons in outer shell |
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Halohydrin Formation Reaction
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Alkene + X2 to yield a halohydrin + HX.
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Stereospecific
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When only a single stereoisomer is produced in a given reaction rather than a mixture.
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Simmons-Smith Reaction
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Alkene + carbenoid + zinc-copper mixture yields a cyclopropane.
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Adam's Catalyst
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PtO2 catalyst used for hydrogenations.
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Hydrogenation of Alkenes Reaction
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aka. Reduction Reactions
Alkene + H2 + catalyst yields an alkane. Heterogenous reaction. |
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Osmium Tetroxide
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OsO4
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Diol
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Aka. Dialcohol , Glycol
Compound containing 2 -OH groups. |
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Hydroxylation Reactions
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Alkene yields a diol through one of 2 paths:
1. Alkene + osmium tetraoxide yields a cyclic osmate. Addition of aqueous sodium bisulfate (NaHSO3) yields a diol. 2. Alkene undergoes epoxidation to yield an epoxide. Epoxide undergoes hydrolysis to yield a diol. |
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Epoxide
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Aka. Oxirane
Cyclic ether with an O atom in a 3-membered ring. |
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Peroxyacid
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RCO3H
Ex. meta-chloroperoxy-benzoic acid |
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Molozonide
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The initial addition product of ozone + an alkene.
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Potassium permanganate
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KMnO4
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3 reagents that cause double-bond cleavage?
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1. Ozone (O3)
2. Potassium Permanganate (KMnO4) 3. Periodic Acid (HIO4) |
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Ozonide
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The product formed by the addition of ozone (O3) to a C=C.
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Monomer
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The simple starting unit from which a polymer is made.
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Polymer
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A large molecule made up of repeating smaller units called monomers.
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Vinyl Monomers
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CH=CHX.
A substituted alkene monomer used to make chain-growth polymers. |