Organic Chemistry I

Chem 334 - Fall 2010

Chapter 6 Skills

Professor Carl C. Wamser

Knowledge - Level 1

know the terminology:

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

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


Applications - Level 3

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