CH630 Advanced Organic Chemistry ( CRN 12618 ) Exam Information

Exam Information

General policies: You may use model sets, calculators or drawing templates. If you feel you need any other aid, please ask me prior to the exam or email me.

Exam 1.

Date, time and location:
Friday, October 31 in class.

Coverage: 
Carey & Sundberg, Chapters 1, 2, and parts of 3 (sections 3.2.2, 3.3, 3.4.1 only) (5th Ed.)
Carey & Sundberg, Chapters 1, 2, 3, and parts of 4 (sections 1, 2 only) (4th Ed.).

• Drawing 3D representations of structures
• Writing resonance structures
• Showing electron flow in mechanisms
• Stereochemical definitions
• Assignment of stereochemical configuration (R/S)
• Energy analysis of conformers, particularly for alkanes and cyclohexane derivatives
• Impact of conformational properties on reactivity: strain; Baldwin's rules; the anomeric effect
• Potential energy diagrams
• The Hammond postulate
• The Curtin-Hammett principle

Post-exam links:

Link to a copy of the exam.
Link to the answer key for the exam.

High score:  89
Average:  66

Exam 2

Date, time and location:
TBA

Expected coverage: 

Carey & Sundberg, 5th Ed.:  Chapters, 3, 4, 5 (sections 5.1-5.3, 5.8. 5.9).
4th Ed.: Chapters 4, 5, 6 (sections 6.1-6.5).

• Formation and stabilization of carbocations

Methods for testing reaction mechanisms:

• Kinetics
• Isotope effects
• Hammett studies and other linear free energy relationships

Nucleophilic substitution:

• S_N1 vs. S_N2
• Structure and stability of carbocations
• Ion pairing
• Leaving group ability
• Stereochemical consequences

Carbocation rearrangements:

• Migratory aptitudes
• Neighboring group participation
• Orientation effects
• "Nonclassical" ions:  2-norbornyl, cyclopropylcarbinyl
• Stereochemical consequences

Post-exam links:

Link to a copy of the exam
Link to the answer key

Final Exam

Comprehensive, with particular emphasis on carbanions, carbenes and radicals (Carey & Sundberg Ch. 7, 12 (4th Ed.) or 6. 11 (5th Ed.), and the distributed material from March).  
Link to the exam
Link to the answer key

High score: 181
Average score: 143

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 Last updated:  09/05/2008
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