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30 Cards in this Set

  • Front
  • Back
  • 3rd side (hint)
Hammond Postulate
Exothermic - transition state resembles starting material

Endothermic - transition state resembles products
transitions states
What does the transition state of chlorination most resemble? Is this exothermic or endothermic?
reactants, and is therefore exothermic
not selective
What does the transition state of bromination most resemble?
products, and is therefore endothermic
Is chloride or bromide more reactive?
not selective
Is chloride or bromide more basic?
Which halogens do not undergo halogenation?
Flouride and Iodide
the only two main halogens aside from chloride and bromide
Benzylic radical is stable or unstable? Is allylic more stable?
stable - benzylic is more stable than allylic
no hint
When is NBS used? (N-bromosuccinimide)What does it react with?
allylic bromination - HOOH heat/hv
no hint
Who is the grandfather of organic synthesis? What's his favorite color
RB Woodward - blue
everybodys favorite color
What is the the rule concerning molecular orbitals called? What does it do?
Woodward-Hoffman Rules - molecular orbitals explain the products of rxns
RB Woodward
What does a large rate constant indicate?
easier to reach transition state
concerns transtion state
What order rxn is Sn2?
second order
dependent on two reactants
What is another name for the umbrella effect that occurs in Sn2?
Walden effect
no hint
What is the strongest base?
least stable
What is the weakest base?
most stable
What is a good leaving group in Sn2?
Weak base like iodide
strong or weak base
What is a good nucleophile in Sn2?
strong base in gas phase
weak base in protic solv.
strong or weak base
What is the best type of solvent for Sn2?
polar, aprotic
no hint
How is the rate of Sn2 determined?
formula for Sn2 rate
How does the molecular orbital theory explain back side attack in Sn2?
HOMO of nucleophile reacts with LUMO of alkyl halide creating an in-phase (bonding) interaction
front side attact would result in a bonding and an antibonding which would cancel out
How do bulky R groups affect Sn2?
steric hinderance which prevent Sn2 if too big
no hint
What is the most reactive alkyl halide in Sn2?

methyl halide or tertiary alkyl halide
methyl halide
does not want bulky groups
Which is a stronger base and therefore a better nucleophile in Sn2?

OH or H2O
no hint
Which is a stronger base and therefore a better nucleophile in Sn2?

no hint
Which is a stronger base and therefore a better nucleophile in Sn2?

NH2 or NH3
no hint
Which is a stronger base and therefore a better nucleophile in Sn2?

no hint
In a protic solvent, what type of nucleophile is preferred
weak base
opposite of aprotic in Sn2
What is ion-dipole interaction?
The interaction between the ion and the dipole of the protic solvent
no hint
Which is the best nucleophile in aqueous sln?

CH3S^(-) or HO^(-)
CH3S^(-) b/c sulfur is larger than oxygen
polar aqueous sln
What is Le Chatelier's principle?
if equilibrium is disturbed, the system will adjust to offset the disturbance