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59 Cards in this Set
- Front
- Back
Which type of molecules cannot undergo Substitution reactions?
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Vinylic Cations and Aryl Cations
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In Sn1, what type of concentration is favored to stabilize charge?
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high concentrations
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What type of solvents stabilize charge?
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Polar Solvents
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List of Protic Solvents
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H20, Formic Acid Methanol, ethanol, tert-butyl alcohol, and Acetic Acid
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Formic Acid
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HCOOH
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Methanol
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MeOH (CH3OH)
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Ethanol
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EtOH (CH3CH2OH)
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Tert-Butyl Alcohol
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(CH3)3COH (tert-BuOH)
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Acetic Acid
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CH3COOH (HoAC)
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List of Aprotic Solvents
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Dimethyl Sulfoxide, Acetonitrile, DMF, Benzene, Hexane
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Dimethyl Sulfoxide
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DMSO
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Acetonitrile
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MeCN
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In a reaction, if the reactants are charged ________________
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the reaction slows down as the reaction continues
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In a reaction, if the intermediate is charged ___________________
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the reaction speeds up as the reaction continues
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Sn2 favors high concentrations of _______________
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aprotic solvents
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Sn1 favors poor nucelophilies in ____________________
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protic solvents
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Intermolecular Reactions
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reaction between 2 molecules to form one molecule
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Intramolecular Reactions
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reaction between one molecule and itself to form a ring structure (prefer 5 & 6)
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What do elimination reactions produce?
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alkenes
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E2 Reaction is a ______________ reaction.
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concerted (1 step)
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Do E2 reactions have a transition state or a intermediate?
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transition state
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What type of stereochemistry does E2 reactions favor?
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antiperiplanar
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Alpha Carbon
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Carbon attached to the halogen
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Beta Carbon
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Carbon adjacent to the alpha carbon
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Dimethyl Sulfoxide
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DMSO
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Do E2 reactions have a transition state or a intermediate?
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transition state
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In cyclic systems, eliminated groups prefer to be in what position?
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axial
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Acetonitrile
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MeCN
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what is also called a Beta-elimination reaction?
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E2
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Do E1 reactions have intermediated or transition states?
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intermediate
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In a reaction, if the reactants are charged ________________
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the reaction slows down as the reaction continues
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In a reaction, if the intermediate is charged ___________________
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the reaction speeds up as the reaction continues
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in E1 reactions, the __________ alkene is formed
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the most stable alkene; carbocation rearrangement can happen
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In E2 reactions, _________ products are more favored than ___________ products
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conjugated; isolated
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Sn2 favors high concentrations of _______________
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aprotic solvents
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Sn1 favors poor nucelophilies in ____________________
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protic solvents
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Tert-Butoxides always:
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eliminate
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In E1 reactions the more ____________ product is usually formed
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substituated
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Benzylic and Allylic carbocation stabilities (3, 2, 1 benzylic and allylic)
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3 Benzylic, 3 allylic, 2 benzylic, 2 allylic, 3 carbocation, 1 benzylic, 1 allylic
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What do elimination reactions produce?
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alkenes
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E2 Reaction is a ______________ reaction.
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concerted (1 step)
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In E2 reactions, _________ products are more favored than ___________ products
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conjugated; isolated
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Tert-Butoxides always:
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eliminate
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What type of nucleophile and solvent do E2 reactions prefer?
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more basic better nucleophiles; aprotic
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What type of nucleophile and solvent do E1 reactions prefer?
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less basic weak nucleophiles; protic
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Deterium Atom
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atom with one proton and one neutron
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Which is more difficult to break, a C-D bond or a C-H Bond?
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C-D Bond
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Deuterium Kintetic Isotope Effect
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Kh/Kd
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What is the maximum of DKIE? and which constant is slower?
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The max is 7.1
Kd is slower than Kh |
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Primary Alkyl Halides only undergo:
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Sn2 and E2 reactions
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Elimination prefers _____ temp
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high
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Substitution prefers ______ temp
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low
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Primary carbocations tend to:
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substitute (Sn1) not eliminate
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Williamson Ether Synthesis
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Preparation of an alloxide
R-Br + R-O- ---> ROR + Br- |
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Hindered Nucleophiles in a Williamson Ether Synthesis do what?
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increase the rate of the reaction
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How are alkynes prepared? Elimination or Substitution
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Double Elimination
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Are alcohols good leaving groups?
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No, so therefore they must be weakened to undergo substitution
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In Substitition reactions, alcohols are _______
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protonated and then replaced with a halogen to react
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In Sn2 reactions of alcohols, if H-CL is used:
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then ZnCl2 or Pyridine is needed to make the reation proceed
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