Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution -- Section 15 of Organic Chemistry Notes is 23 pages in length (page 15-1 through page 15-23) and covers ALL you'll need to know on the following lecture/book topics:

SECTION 15 – Electrophilic Aromatic Substitution

15-1 -- The Chemistry of Benzene (C6H6)
15-1 -- General Mechanism of Electrophilic Aromatic Substitution (E.A.S.)
_· Delocalization of Charge
_· An Addition Reaction is Not Observed
15-2 -- Overview of Electrophilic Aromatic Substitution Reactions
_· Nitration (Adding –NO2 to the Benzene Ring)
_· Sulfonation (Adding –SO3H to the Benzene Ring)
_· Halogenation (Adding “-X” to the Benzene Ring)
_· Friedel-Crafts Alkylation (Adding “-R” to the Benzene Ring)
_· Friedel-Crafts Acylation (Adding “-COR” to the Benzene Ring)
15-3 -- The Nitration Reaction
_· Detailed Mechanism
_· Product is Nitrobenzene
15-3 -- The Sulfonation Reaction
_· Product is Benzenesulfonic Acid
_· Detailed Mechanism
_· Use of “Fuming Sulfuric Acid”
_· Le Chatelier’s Principle and Possible Desulfonation
_· Principle of Microscopic Reversibility
15-5 -- Halogenation of Aromatic Rings
_· Product is a Halobenzene
_· Use of the Lewis Acid Catalyst, FeCl3
_· Detailed Mechanism
_· Iodination – Mechanism is a Bit Different (CuCl2 as Catalyst)
15-6 -- Friedel-Crafts Alkylation
_· Doesn’t Proceed on Aromatic Rings with Strongly Deactivating Substituents
_· Detailed Mechanism – Works Well with R-Cl, R-Br, R-I, or R-F
_· Rearrangements of “R” and the Involvement of Free Carbocations
15-8 -- Friedel-Crafts Acylation
_· The “Acyl Group”
_· Detailed Mechanism
_· The “Acylium Ion” – Not Prone to Rearrangement
15-9 -- Use of H+ (D+) as the Electrophile
15-10 -- Directing Effects of Substituents

_· Ortho (o), Meta (m), and Para (p) Directors
_· Activators vs. Deactivators
_· Mechanism of Para Attack by an Electrophile
_· Mechanism of Ortho Attack by an Electrophile
_· Mechanism of Meta Attack by an Electrophile
15-11 -- More on Activating, o,p-Directoring Groups
_· “Electron-Withdrawing” – Induction vs. Resonance
15-13 -- More on Deactivating, m-Directoring Groups
15-13 -- Halogens are o,p-Directors and Weak Activators
15-14 -- Detailed Summary of Substituents’ Directing Effects

_· Activating, o,p-Directors (Both Strong and Weak)
_· Deactivatinig, m-Directors (Both Strong and Weak)
_· Deactivating, o,p-Directors (Weak)
15-14 -- Miscellaneous Notes About E.A.S Reactions
_· Important Side Notes on Friedel-Crafts Reactions
_· Ortho-Para Product Ratio is Sensitive to Steric Effects
_· Important Substituent Transformations (i.e. –NO2 converted to –NH2)
_· What if 2 or More Substituents’ Directing Effects Oppose Each Other?
15-17 -- Organic Synthesis of Benzene Derivatives
_· The Order of Reactions is Critical
15-18 -- Nucleophilic Aromatic Substitution Reactions (N.A.S.)
_· Mechanism #1: Addition-Elimination
_· Meisenheimer Complex
_· Need a Good Leaving Group (l.g.) and an Electron-Withdrawing Group
_· Mechanism #2: Elimination-Addition
_· Occurs via “Benzyne” Mechanism
_· Need a Very Strong Base
15-21 -- Benzyne Can Act as a Dienophile and React with Dienes
15-22 -- Side-Chain Oxidation Reactions (Use of KMnO4)
15-22 -- Benzylic Bromination Reactions

_· Occurs via a Free Radical Chain Mechanism
_· NBS = N-Bromosuccinimide

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Electrophilic Aromatic Substitution

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