Below is a comprehensive list of topics that you need to familiarize yourself with for
The exam will have one major spectroscopy question, and a few short minor
There are a few supply reagent/product questions.
there may be a some multistep synthesis questions.
Unavoidably, the exam will have some multiple choice questions to cover some of the
earlier topics (like ‘which molecule containing a carbocation is the most stable,
which is the strongest acid, etc.). Approximately 50% of the exam will revisit topics
from problem sets I assigned (not the book problems) and exams 1-4 from this
You are allowed one 5x7 signed reaction card for the exam (both sides covered with
reactions and/or reagents). This will be turned in with the exam.
Here is a modified syllabus and associated notes on the reactions and concepts you
are responsible for.
Part I. The Structure of Organic Compounds
Introduction and organic nomenclature 1.1, 2.1, 2.2, 2.4, 2.5, 2.7, 2.9
Bonding in organic compounds 1.2-1.9
Lewis Dot structures
Identifying functional groups
Atomic and Molecular Orbital Theory
Hybridized orbital geometries (sp,sp2, sp3)
Sigma, pi, sigma*, pi* relationships
Drawing resonance structures, energies from resonance structures
Alkanes, alkenes, alkynes & conformational analysis 2.3, 4.1-4.5
Newman projections, dihedral relationships and energy diagrams
Bonding differences between alkenes and alkynes
Highly substituted alkenes are more stable than less substituted alkenes
Cycloalkanes & conformational analysis 7.1-7.6
Energy and ring size (cyclopropane, butane, pentane, hexane)
Strain, idealized bond angles and strain, torsional strain
Conformations of 3,4,5,6 membered rings and associated energy diagrams
Preferred conformations of rings and substituent effects (which is most stable
Stereochemistry 6.1-6.11 (6.12)
Representing stereochemistry in structures (dashs, wedges)(R/S; E/Z assignments; Cahn-
Ingold Prelog assignments)