Chem 334 - Fall 1999
Organic Chemistry I

Dr. Carl C. Wamser

Chapter 6 Skills

Knowledge - Level 1

know the terminology:

homolytic / heterolytic (for bond breaking)
homogenic / heterogenic (for bond making)
nucleophile / electrophile (electron-pair donor / acceptor)
endothermic / exothermic (absorbs / releases heat energy)
regiochemistry / regioselectivity
stereochemistry / stereoselectivity
syn / anti additions
oxidation / reduction reactions

know the rules:

Markovnikov Rule for addition to double bonds

Concepts - Level 2

understand the naming of reaction types (what happens?)
e.g., hydrogenation, halogenation, etc.

understand the typical manner of displaying organic reactions
(reactants, reagents, solvents, conditions, products)

understand the concept of dynamic equilibrium
(reversible interconversion of reactants and products)

understand the distinction between thermodynamics and kinetics
(equilibrium versus rate)

understand the use of electron-pushing arrows to show electron flow

understand the concept of a reaction mechanism
(a step-by-step account of how a reaction occurs)

understand the features of a reaction energy diagram
(activation energy, Ea, and heat of reaction, delta H)

understand the concept of a transition state
(the transient molecular structure at the peak of energy, Ea)

understand the structure and reactivity of a carbocation
(trigonal planar, sp2, strong electrophile)

understand why electron-donating groups stabilize a carbocation

recognize that the Markovnikov Rule is based on carbocation stability
(more highly substituted carbocations are favored)

Applications - Level 3

classify organic reactions as to type:
(addition, elimination, substitution, rearrangement)

label the main features of a reaction energy diagram
(Ea, delta H, transition state, the axes)

draw an appropriate reaction energy diagram, given Ea and delta H

follow the electron flow in an given reaction using electron-pushing arrows

identify nucleophiles and electrophiles in a given reaction

use the Markovnikov Rule to predict addition products

write or recognize specific instances of the reactions of alkenes:

addition of HX
addition of water
addition of halogen (anti)
addition of hydrogen (syn)
oxymercuration/reduction (to an alcohol)
hydroboration/oxidation (to an alcohol)
oxidative addition (to a diol)
oxidative cleavage (by ozone)

Analytical Skills - Level 4

write mechanisms for any of the above reactions, specifically illustrating any intermediates, regiochemistry or stereochemistry

propose possible reaction mechanisms for a given reaction

propose a possible transition state structure for a given reaction

create a reaction energy diagram for a given reaction

Synthetic Skills - Level 5

use an appropriate reaction or sequence of reactions to create a target molecule