Chem 334 - Fall 1999
Organic Chemistry I
Dr. Carl C. Wamser

Chapter 8 Skills

Knowledge - Level 1

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
anti periplanar
Zaitsev Rule

Concepts - Level 2

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

Applications - Level 3

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

Analytical Skills - Level 4

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

Synthetic Skills - Level 5

use an appropriate reaction or sequence of reactions to create a target molecule