CHE 232-002

Facts and Skills to Master for the Third Exam

The second exam will cover Chapters 1 to 21 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 and second exams and in CHE 230.

You should be able to predict the correct product of the reaction of a substituted benzene in an electrophilic aromatic substitution reaction.

You should be able to predict the major product (or lack of products) of each of the following reactions:

• ArNO₂ and SnCl₂ or H₂, Pd/C
• ArNH₂ and NaNO₂, aq. HCl
• RN₂⁺ and:
  • CuCl, CuBr, CuCN, or aq. Cu₂O
  • KI
  • BF₄^–
  • H₃PO₂
• An aryl bromide or iodide and:
  • RSnMe₃ in the presence of cat. Pd(0), phosphine
  • RB(OH)₂ in the presence of cat. Pd(0), phosphine, and base (the C attached to B must be sp²-hybridized)
  • ROH, RNH₂, or R₂NH in the presence of cat. Pd(0), phosphine, and base
• A carbonyl compound or nitrile and:
  • RLi or RMgX
  • LiAlH₄, NaBH₄, or DIBAL (i-Bu₂AlH)
• An alcohol or aldehyde and PCC or Jones reagent (CrO₃, aq. H₂SO₄)
• A ketone or aldehyde and:
  • H₂O or ROH under acidic or basic conditions
  • a 1,2-diol under acidic conditions
  • NH₃, RNH₂, or R₂NH under acidic or basic conditions
  • Ph₃P=CR₂

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 reactions above and previously studied reactions.

You should be able to draw mechanisms for reactions involving carbonyl compounds reacting with nucleophiles. You should also be able to draw mechanisms for:

• nucleophilic aromatic substitutions
• the formation of iminium ions and their reactions with nucleophiles

You should understand and be able to explain why aryl halides do not generally react with nucleophiles, unless the rings are electron-poor or Pd is used. You should be able to explain how using Pd allows aryl bromides to react with nucleophiles.

You should be able to explain the differences in reactivity between different kinds of carbonyl compounds. For example, you should be able to explain why esters react with hydrides or organometallic compounds to give alcohols, whereas Weinreb amides stop at the ketone or aldehyde. You should understand and be able to explain how 1,2-ethanediol can allow you to do chemistry on less reactive carbonyl compounds such as esters without affecting ketones and aldehydes.

You should understand and be able to explain the factors that affect the position of the equilibrium between ketones or aldehydes on the one hand, and hemiacetals, acetals, imines, and enamines on the other.

You should understand and be able to explain why hemiacetals can form under both basic and acidic conditions, but acetals can form and react only under acidic conditions. You should understand and be able to explain why iminium ion formation becomes slower as reaction conditions are made more strongly basic or acidic.

Return to the Grossman CHE 232 page.

Return to CHE 232 page

Return to Course Listing

Return to the UK Chemistry Home Page