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Chap05 - Alkene/Alkyne Reactions ADDITION ELIMINATION...

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Alkene/Alkyne  Reactions ADDITION & ELIMINATION Hydration & dehydration examples of addition and elimination reactions involving alkenes in previous chapter. ADDITION REACTIONS Add'n Name Mechanism H"X" hydrohalogenation electrophilic addition "X 2 " halogenation electrophilic addition
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HOH hydration electrophilic addition H 2 hydrogenation addition
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C H 2 CH 2 + HCl(g) organic solvent CH 2 CH 2 H Cl + H-H transition metal + H-OH acid solvent + Br-Br organic CH 2 CH 2 Br Br CH 2 CH 2 H OH CH 2 CH 2 H H
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Some Electrophilic Addition  Mechanisms C H 2 CH 2 + H Cl CH 2 CH 2 H + + .. :Cl: .. - C H 2 CH 2 Cl H
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C H 2 CH 2 + H O + H H C H 2 CH 2 H + + OH 2 .. .. C H 2 CH 2 H O + H H C H 2 CH 2 H OH
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C H 2 CH 2 Br Br + C H 2 Br CH 2 + + Br    C H 2 CH 2 Br Br Bromonium ion Bridging ion occurs with chlorine too. Bromonium or chloronium ion hogs all of the space on one side of both carbons. Forces bromide anion to approach from opposite side of double bond. What difference does this make? Often cannot tell from product that bromonium ion intermediate was formed. Sometimes you can tell, however. Example cyclohexane reacting with bromine (next page).
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C H 2 C H 2 CH 2 CH CH CH 2 + Br Br C H 2 C H 2 CH 2 CH CH CH 2 Br + Br - Br H Br H Trans addition to double bond makes trans product (diequatorial). +
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What about addition reactions which don't form bridged cations? When a carbocation is formed as an intermediate, which of the two double-bond carbons gets the stick and which is stuck with the charge (carbocation)? C H 3 CH 2 CH CH 2 HBr HBr C H 3 CH 2 CH CH 2 H + C H 3 CH 2 CH CH 2 H + ????? POSSIBLE PRODUCTS: C H 3 CH 2 CH CH 2 H Br C H 3 CH 2 CH CH 2 H Br This product is major product.
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