CHE 230-002

Facts and Skills to Master for the Final Exam

The final exam will cover Chapters 1-12 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, second, and third exams.

You should understand the mathematical relationships among free energy, enthalpy, entropy, and equilibrium constant. You should be able to compare the energies of products, starting materials, and transition states of two reactions and draw conclusions about their relative rates and exothermicities. You should be able to express these values graphically in a reaction coordinate diagram.

Given the starting materials and reaction conditions, you should be able to draw the product of the reaction of an alkene with the various reagents we have discussed:

• HX (strong mineral acid)
• H₂O, ROH, or RCO₂H, cat. H₂SO₄
• BH₃, then H₂O₂ and base
• X₂ (elemental halogen)
• NBS or X₂ and H₂O, ROH, or RCO₂H
• H₂, Pd/C
• RCO₃H (a peracid, such as mCPBA)
• RCO₃H, then a basic nucleophile such as HO^– or RC≡C^–
• CHCl₃, base
• CH₂I₂, Zn(Cu)
• OsO₄, then aq. NaHSO₃
• O₃, then Me₂S
• HBr, cat. peroxide or air
• cat. peroxide (free-radical polymerization)
• diene (Diels–Alder reaction)

Given the starting materials and reaction conditions, you should be able to draw the product of the reaction of an alkyne with the various reagents we have discussed:

• HX (strong mineral acid)
• H₂O, cat. HgSO₄, cat. H₂SO₄
• BH₃, then H₂O₂ and base
• X₂ (elemental halogen)
• H₂, Pd/C
• H₂, Lindlar cat.
• Li or Na, liq. NH₃
• HBr, cat. peroxide or air
• strong base, then a primary alkyl halide.
• diene (Diels–Alder reaction)

For each reaction with an alkene or alkyne, you should be able to draw the product with the correct regiochemistry (Markovnikov or anti-Markovnikov) and the correct stereochemistry (syn, anti, or nonselective), where applicable.

Given the starting materials and reaction conditions, you should be able to draw the product of the reaction of an alkane with the various reagents we have discussed:

• X₂ (elemental halogen) or NBS, hν
• O₂

For each reaction with an alkane, you should be able to predict which H atom in a compound will be replaced.

Given the starting materials, products, and reaction conditions, you should be able to draw the mechanism for the following reactions.

• Alkenes:
  • HX (strong mineral acid)
  • H₂O, ROH, or RCO₂H, cat. H₂SO₄
  • X₂
  • NBS or X₂ and H₂O, ROH, or RCO₂H
  • CHCl₃, base
  • HBr, cat. peroxide or air
  • cat. peroxide (free-radical polymerization)
  • diene (Diels–Alder reaction)
  • S_N2' substitution of allylic halides
• Alkynes:
  • X₂ (elemental halogen)
  • Li or Na, liq. NH₃
  • strong base, then a primary alkyl halide.
  • diene (Diels–Alder reaction)
• Alkanes:
  • NBS or X₂ (elemental halogen), hν
  • O₂

  A particular reaction may involve elemental steps taken from more than one of these mechanisms.

Given a target compound, you should be able to design its synthesis from simpler starting materials via the reactions noted above and those we have learned previously.

Given some information about a reaction, you should be able to make arguments about it (whether it will work, why a particular product is not obtained, etc.) based on your knowledge of the reaction and its mechanism. You should also be able to apply this knowledge to a reaction that you have not seen before.

You should be able to use the concept of alkene conjugation to explain vinylogous reactions (such as S_N2' substitution) and physical properties of polyenes (such as color).

You should be able to explain why a particular diene–dienophile pair would react quiickly or slowly in a Diels–Alder reaction.

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