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59 Cards in this Set

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