Course Objectives for Exam 2

Organic Chemistry I

Chem 243

Fall 2011

10/25/2011

Chapters 4, 5 and 6

Nomenclature

Be able to provide IUPAC names for given structures and draw structures given IUPAC or common names.

Conformational Analysis

Know how to use Newman projections and how they are used to represent conformations.  Be able to draw given conformations (you will be given a blank template for the Newman projection).

Regarding cyclohexane rings, you should know how to draw chair conformations (you will be given templates and will have to insert substituents).

Know what conformation is the most stable (lowest energy) and how a conformational change (ring flip) will effect the conformation.

Understand thoroughly axial and equatorial positions, cis and trans isomers when applied to rings, and mirror images of rings.

Stereochemistry

Be able to identify stereogenic centers in a given molecular structure and determine how many chiral centers are present.

Be able to determine the stereochemical relationship between molecules, i.e., enantiomers, diastereomers, meso  compounds, identical compounds, or not stereoisomers, etc.

Know  how to assign R and S configurations to molecules with stereogenic centers, using Fisher projectionsn,  and include them in  correct IUPAC names.

Reactions

Given a set of reactants, you should be able to provide the structure of the major product of the resulting reaction.  This will be mainly nucleophilic substitution and elimination reactions.  Draw neat structures!!!  This is a major part of the exam.  Make sure you can identify a species as a nucleophile, see table in textbook.

Know how solvents can effect rates of reactions.  Study transition state theory and reaction  coordinate diagrams to  understand this.

Mechanisms

Know SN1, SN2, E1 and E2 mechanisms.  Know the intermediates formed in  each.  Be able to write a mechanism for a given reaction.

Know which conditions , e.g. solvent, concentrations, substrates,etc.  will favor each mechanism.

Understand the nature of good nucleophiles and leaving groups.

Do not confuse transition states with intermediates.

Be able to identify substrates, leaving groups and nucleophiles.

Know how the kinetics and thermodynamics of a reaction can be employed to control the rate of the reaction.

Carbocations

Understand carbocations and their relative stability and the mechanisms in which they are involved.