CHE 232-002

Facts and Skills to Master for the Final Exam

The third exam will cover Chapters 1 to 24 and sections 13 and 14 of Chapter 25 in Smith. 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, second, and third exams and in CHE 230.

Given a target compound and a description of acceptable starting materials, you need to be able to design a synthesis of the target from the starting materials using the following reactions and previously studied reactions:

• Reactions of carbonyl compounds with alkyl halides:
  • An enolate of a ketone, ester, nitrile, or amide + an alkyl halide
  • A ketone, ester, or nitrile + an alkyl halide under moderate basic conditions
• Reactions of carbonyl compounds with ketohydes:
  • An enolate of a ketone, ester, nitrile, or amide + a ketohyde
  • An aldehyde, ketone, ester, or nitrile + a ketohyde under moderate basic conditions
  • An aldehyde or ketone + a ketohyde under acidic conditions
• A ketone, ester, or nitrile + an ester with at least one equivalent of a moderate base
• A 1,3-dicarbonyl compound + an α,β-unsaturated carbonyl compound with a catalytic amount of a moderate base
• An acyl halide, acyl anhydride, thioester, aldehyde, or ketone + Br₂ under acidic conditions.

You should be able to draw mechanisms for the reactions above.

You should be able to explain why different kinds of carbonyl compounds require acidic or basic conditions to react with various kinds of electrophiles. You should be able to explain why the Claisen and Dieckmann condensations require a stoichiometric amount of base, whereas the aldol and Michael reactions require only a catalytic amount of base.

Return to the Grossman CHE 232 page.

Return to CHE 232 page

Return to Course Listing

Return to the UK Chemistry Home Page