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Organic Chemistry I |
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Professor Carl C. Wamser |
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Chapter 8 Skills |
know the terminology:
nucleophile
nucleophilic substitution
protic / aprotic solvents
dielectric constant
SN1, SN2, E1, E2
leaving group
inversion of stereochemistry
unimolecular / bimolecular
first-order / second-order kinetics
rate-determining step
steric effects / beta-substituents
understand the implications of a mechanism on the rate law for the reaction
unimolecular rate-determining step will show first-order kinetics
bimolecular rate-determining step will show second-order kinetics
understand the implications of a mechanism on the stereochemistry of the reaction
recognize the key features of the SN2 mechanism:
concerted backside attack of nucleophile
recognize the key features of the SN1 mechanism:
two-steps - rate-determining ionization, then reaction with nucleophile
recognize the key features of the E2 mechanism:
concerted anti periplanar elimination of H and X
recognize the key features of the E1 mechanism:
two-steps - rate-determining ionization, then loss of H+
recognize that substitution and elimination are often competitive reactions
identify various nucleophiles
predict relative nucleophilicity
predict products of nucleophilic substitution reactions on alkyl halides, including stereochemistry
predict elimination products from alkyl halides, including stereochemistry and the application of the Zaitsev Rule
predict the preferred reaction mechanism(s) for a given alkyl halide under specified conditions: SN2, SN1, E2, E1
predict the best conditions to carry out a nucleophilic substitution reaction on a given alkyl halide
predict the best conditions to carry out an elimination reaction on a given alkyl halide
use an appropriate reaction or sequence of reactions to create a target molecule