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30 Cards in this Set
- Front
- Back
- 3rd side (hint)
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Hammond Postulate
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Exothermic - transition state resembles starting material
Endothermic - transition state resembles products |
transitions states
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What does the transition state of chlorination most resemble? Is this exothermic or endothermic?
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reactants, and is therefore exothermic
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not selective
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What does the transition state of bromination most resemble?
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products, and is therefore endothermic
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selective
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Is chloride or bromide more reactive?
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chloride
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not selective
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Is chloride or bromide more basic?
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bromide
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selective
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Which halogens do not undergo halogenation?
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Flouride and Iodide
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the only two main halogens aside from chloride and bromide
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Benzylic radical is stable or unstable? Is allylic more stable?
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stable - benzylic is more stable than allylic
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no hint
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When is NBS used? (N-bromosuccinimide)What does it react with?
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allylic bromination - HOOH heat/hv
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no hint
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Who is the grandfather of organic synthesis? What's his favorite color
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RB Woodward - blue
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everybodys favorite color
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What is the the rule concerning molecular orbitals called? What does it do?
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Woodward-Hoffman Rules - molecular orbitals explain the products of rxns
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RB Woodward
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What does a large rate constant indicate?
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easier to reach transition state
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concerns transtion state
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What order rxn is Sn2?
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second order
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dependent on two reactants
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What is another name for the umbrella effect that occurs in Sn2?
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Walden effect
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no hint
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What is the strongest base?
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Flouride
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least stable
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What is the weakest base?
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Iodide
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most stable
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What is a good leaving group in Sn2?
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Weak base like iodide
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strong or weak base
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What is a good nucleophile in Sn2?
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strong base in gas phase
weak base in protic solv. |
strong or weak base
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What is the best type of solvent for Sn2?
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polar, aprotic
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no hint
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How is the rate of Sn2 determined?
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rate=k[electrophile][nucleophile]
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formula for Sn2 rate
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How does the molecular orbital theory explain back side attack in Sn2?
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HOMO of nucleophile reacts with LUMO of alkyl halide creating an in-phase (bonding) interaction
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front side attact would result in a bonding and an antibonding which would cancel out
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How do bulky R groups affect Sn2?
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steric hinderance which prevent Sn2 if too big
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no hint
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What is the most reactive alkyl halide in Sn2?
methyl halide or tertiary alkyl halide |
methyl halide
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does not want bulky groups
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Which is a stronger base and therefore a better nucleophile in Sn2?
OH or H2O |
OH
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no hint
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Which is a stronger base and therefore a better nucleophile in Sn2?
CH3OH or CH3O |
CH3O
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no hint
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Which is a stronger base and therefore a better nucleophile in Sn2?
NH2 or NH3 |
NH2
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no hint
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Which is a stronger base and therefore a better nucleophile in Sn2?
CH3CH2NH or CH3CH2NH2 |
CH3CH2NH
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no hint
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In a protic solvent, what type of nucleophile is preferred
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weak base
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opposite of aprotic in Sn2
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What is ion-dipole interaction?
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The interaction between the ion and the dipole of the protic solvent
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no hint
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Which is the best nucleophile in aqueous sln?
CH3S^(-) or HO^(-) |
CH3S^(-) b/c sulfur is larger than oxygen
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polar aqueous sln
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What is Le Chatelier's principle?
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if equilibrium is disturbed, the system will adjust to offset the disturbance
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equilibrium
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