CHE 232-002

Facts and Skills to Master for the Third Exam

The third exam will cover Chapters 1-8 in Jones. The following guidelines are not meant to be complete or comprehensive lists of the information you are expected to know.


You are expected to have command of all the material covered on the first and second exams.

You should be able to draw an amine, alcohol, ether, sulfide, or thiol whose name is provided.

Given the starting materials and reaction conditions, you should be able to draw the product of the reaction of an alkyl halide or an alcohol with a base or nucleophile, including the stereochemical result.

Given the starting materials and products of a reaction, you should be able to draw the reagent that was used to execute the reaction. You should also be able to tell whether the reaction needed to occur under acidic or basic conditions.

Given the starting materials, products, and reaction conditions, you should be able to draw the mechanism of an SN2, E2, SN1, or E1 reaction using the curved arrow convention to show the movement of electrons. The SN1 and E1 reactions may include carbocation rearrangements.

Given a target compound, you should be able to design its synthesis from simpler starting materials via substitution or elimination reactions.

You should be able to explain how changes in the alkyl halide, the base or nucleophile, and the solvent will affect the rate of a substitution or elimination reaction or the proportion of substitution and elimination products.

You should understand what makes reactions fast or slow and exothermic or endothermic. You should be able to convert information about a reaction's rate and energy into a reaction coordinate diagram, and vice versa. You should be able to explain and apply the Hammond postulate.


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