R340 Exam 2 Review Sheet
Format of exam:
 The format of the exam will be 100 pts divided into individual or multipart problems. (See the
practice exam for structure.)
 The format of individual problems will be exactly the same as the homework.
 A significant number of problems will be directly from problems you have seen in homework or
review sheets or very closely related.
 Most of the rest of the problems will be based upon homework problems.
Study suggestions:
 Review all homework by attempting to redo them without reference to answers.
 Review notes. Based on what we studied, come up with your own questions. Work in teams
and test each other.
 Take a practice exam as if it is a real exam, then check your answers
Topics and example problems:
 Intermolecular forces: You should be able to describe specific types of intermolecular forces
within the context of particular molecules. You should be able to explain how intermolecular
forces affect water solubility and molecular recognition.
1. Which of these two molecules is more water soluble? Explain.
2. Describe the active site of an enzyme that would recognize this molecule:

Acid/base chemistry: You should be able to identify Bronsted acid/bases and write acid base
reactions. You should be able to compare the strengths of acids and bases using pKa’s and
stability principles from class. You should understand and be able to apply relationships
between acid/conjugate base and strength/stability of base. You should be able to predict
the direction of equilibrium of an acid/base reaction qualitatively and quantitatively. You
should be able to predict the products of an acid/base reaction.
1. Label the acid, base, conjugate acid, and conjugate base. What are the pKa values of the acids? In
which direction does the equilibrium lie?
2. Draw mechanistic arrows for this acid/base reaction, then draw simplified orbital overlap pictures for
the two bases. Use base stability principle(s) to indicate which base is more stable.

Addition reactions: You should be able to draw a mechanism for an electrophilic addition of
HX or H+/HOR to an alkene. You should be able to draw an energy diagram for addition
reactions. You should be able to explain the stereochemical and regiochemical outcome of an
addition reaction based on physical description of the carbocation. You should be able to
predict the major product(s)of an addition reaction. You should be able to provide the
reagents necessary for an addition reaction.
1. Fill in the boxes with reagents or products as appropriate:
2. Draw a mechanism for formation of the Markovnicov product. Draw energy diagrams to explain why
the Markovnicove product is the major product.

Elimination reactions: You should be able to draw a mechanism for an elimination of an alkyl
halide using a strong base and an alcohol using acid catalyst. You should be able to draw an
energy diagram for elimination reactions and explain why the equilibrium is shifted toward
the products. You should be able to predict the major product(s)of an elimination reaction.
You should be able to provide the reagents necessary for an elimination reaction.
1. Provide reagents for these elimination reactions:
2. Draw an arrow mechanism for this reaction. Draw an energy diagram for the reaction, and explain
why the reaction is exothermic even though a pi bond is formed and a sigma bond is lost.

Nucleophilic Substitution Reactions: recognize strong nucleophiles, leaving groups,
electrophiles, draw mechanism, inversion of stereochemistry, steric hindrance, epoxides
1. Draw products, including stereochemistry for these substitution reaction s.

Principles of Mechanism and Energetics: You should be able to draw products of a reaction
given arrows and you should be able to draw arrows given reactants and products. You
should be able to recognize Lewis bases (nucleophiles) and Lewis acids (electrophiles.) You
should be able to label a reaction as a substitution, elimination, or addition. You should be
able to draw an energy diagram with correct relative energies for single and multiple step
reactions. You should be able to draw a transition state structure. You should understand the
difference between thermodynamics and kinetics and when each apply
These questions will often be part of other questions—see above.
1. Draw an energy diagram for a two step reaction which is endothermic with the first step being rate
determining.