Organic Chemistry II
	Professor Carl C. Wamser
Chem 335 - Winter Term	Chapter 12 Skills

Aromatic Substitution

Knowledge - Level 1

Terminology:

activating, deactivating
substituent effects
directing effects
Friedel-Crafts reaction
partial rate factor
benzyne

Concepts - Level 2

know the general reaction mechanisms for electrophilic and nucleophilic aromatic substitution

recognize the effect of substituents in stabilizing or destabilizing an intermediate carbocation or carbanion (activating or deactivating effects)

recognize the directing effects of substituents as a special case of stabilizing or destabilizing an intermediate (ortho, para- or meta-directors)

understand the differences in structure and reactivity between alkyl halides and aryl halides

Applications - Level 3

identify the various strong electrophiles (and how they are generated) for different electrophilic aromatic substitution reactions:

bromination (Br+ from Br2 + FeBr3)
chlorination (Cl+ from Cl2 + FeCl3)
nitration (NO2+ from HNO3 + H2SO4)
sulfonation (SO3H+ from SO3 + H2SO4)
alkylation (R+ from RCl + AlCl3)
acylation (RCO+ from RCOCl + AlCl3)

be able to generate the resonance forms of an intermediate benzenium ion
(including in the presence of an existing substituent on the ring)

identify expected products from electrophilic or nucleophilic aromatic substitution

Analytical Skills - Level 4

classify substituents based on their electron donating or withdrawing characteristics

explain why a given substituent acts as activating or deactivating

explain why a given substituent acts as an ortho, para- director or a meta-director

Synthesis Skills - Level 5

design a synthetic sequence for a given target compound, typically starting from benzene