Chapter 6 Skills

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

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Concepts - Level 2

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

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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)

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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

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Synthetic Skills - Level 5

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