CHE 230-002

Facts and Skills to Master for the Final Exam

The final exam will cover Chapters 1–11 in Klein. 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.

You should be able to draw the product of the following reactions, correctly predicting both the regiochemistry and the stereochemistry.

• An alkene with:
  • a strong acid HX
  • H₂O or ROH and cat. acid
  • BH₃, then H₂O₂ and aq. NaOH
  • H₂ and cat. Pd/C
  • X₂ (where X is Br or Cl)
  • NBS or NCS and H₂O or ROH
  • mCPBA
  • cat. OsO₄, aq. NMO
  • O₃, then Me₂S
  • HBr and cat. peroxide or O₂
• An alkyne with:
  • a strong acid HX
  • H₂O, cat. HgSO₄, cat. acid
  • R₂BH, then H₂O₂ and aq. NaOH
  • H₂ and cat. Pd/C
  • H₂ and cat. Lindlar catalyst
  • Li, liq. NH₃
  • X₂ where X is Br or Cl
  • when the alkyne is terminal, strong base followed by C(sp³)–X
• An epoxide with:
  • an anionic nucleophile, such as HO^–
  • a protic, neutral nucleophile, such as H₂O or ROH, and cat. acid
• An alkane with:
  • X₂ (where X is Br or Cl), NBS, or NCS and light, cat. peroxide, or O₂
  • O₂

You should be able to draw mechanisms for the reactions of an alkene with:

• a strong acid HX
• H₂O or ROH and cat. acid
• X₂ (where X is Br or Cl)
• NBS or NCS and H₂O or ROH
• mCPBA
• HBr and cat. peroxide or O₂

You should be able to explain the regiochemistry and stereochemistry of any of the reactions above by reference to the reactive intermediates.

You should be able to identify reactions that proceed by a free radical mechanism, and you should be able to correctly draw chain mechanisms for those reactions.

Given a target compound, and using one or more of the reactions above, you should be able to design its synthesis from starting materials with given characteristics. (Look for retrons and do disconnections or functional group interchanges.)

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