Chap04 - C H 2 CH 2 H OH C H 2 CH 2 dry hydrophilic Acid...

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Reaction Types C Br KOH C OH + KBr + S UBSTITUTION REACTION C H 2 CH 2 Br H C H 2 CH 2 + HBr ELIMINATION REACTION
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C H 2 CH 2 + HBr C H 2 CH 2 Br H ADDITION REACTION
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Mechanism Reactants f Intermediates f Products Typical Intermediates: C H 3 C CH 3 CH 3 + CARBOCATION C H 3 C CH 3 CH 3 C H H RADICAL
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C H 3 C CH 3 CH 3 - CARBANION Reaction Sites Polar Bonds
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Multiple Bonds Functional Groups
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Lewis Acid/Base A Lewis base contains atoms with one or more pairs of eyeballs (electrons) which can seek out positive charges and eyeball- deficient atoms A Lewis acid contains atoms with some positive charge or lacking eyeballs - will seek out eyeballs. N C H 3 C H 3 C H 3 Eyeballs
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Lewis Base (Nucleophile)
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Vacant "p" orbital (missing eyeballs - Help me I'm blind!!) B F F F Lewis Acid (Electrophile) C H 3 C C H 3 O + : : Nucleophilic Site Electrophilic Site Skip Section 4.4 Halogenation of Alkanes
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Elimination Rxns DEHYDROHALOGENATIONS C H 2 CH 2 H Br C H 2 CH 2 Base C H CH Br Br H H C H CH Base C H CH H Br H Br C H CH Base
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DEHYDRATION
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Unformatted text preview: C H 2 CH 2 H OH C H 2 CH 2 dry hydrophilic Acid Reaction establishes equilibrium (can be run in both directions). Excess water (product) drives reaction to left. Dry acid which holds onto water and won't let it react easily with alkene (ie. H 2 SO 4 or H 3 PO 4 ) helps to drive reaction to right. Reaction can only eliminate one molecule of water to form alk e nes. Cannot be used to form alk y nes. ORIENTATION: SAYTZEFF'S RULE Double bond carbons would rather be attached to fellow carbons than to hydrogens. C C CH 2 CH 3 H C H 3 Br H CH 3 ? Base C C CH 2 CH 3 H C H 3 CH 3 C C CH 2 CH 3 C H 3 H CH 3 NO! YES! Mechanism Everything but reactant (first) and product (last) is an intermediate ....
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Chap04 - C H 2 CH 2 H OH C H 2 CH 2 dry hydrophilic Acid...

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