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l14 - O H H H3C O H H3C O CH3 A B C Which alkene is the...

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A B C Which alkene is the most stable? Why? Alkenes are electron deficient Alkyl groups are electron donor groups. O O O A B C H H H H 3 C CH 3 H 3 C Which carbonyl is the most stable? Why? Carbonyl carbons are electron deficient Alkyl groups are electron donor groups. H H H + H H H H H H H H H R R H 2 O R R R R O H H R R O H H 2 O O Do the same reaction with a ketone R R Do the same reaction with a ketone. What is the product? O O H H O R O R R R R O O H H H A B C D E F R R R R O H R O O O O H H R R O H H H H + H H H H H H H H H R R H 2 O R R R R O H H R R O H H 2 O O H + O H O H O H R R R R R R O H H R R O H H 2 O H 2 O Hydrate or di l O H gem -diol R R O O O A B C H H H H 3 C CH 3 H 3 C Which carbonyl would form the most stable hydrate? O H Which has largest K eq ? H H O H 2 O + H H O H K eq = 2000 H O H 2 O + H 3 C H O H K eq = 1.3 O O H H 3 C O H K 0 002 H 3 C CH 3 H 2 O + H 3 C CH 3 O H eq = 0.002 O O H Cl 3 C H H 2 O + Cl 3 C H O H Will K be higher (A) or lower (B) eq than for acetaldehyde? H O H 2 O + H 3 C H O H K eq = 1.3 O O H K 0 002 H 3 C O H H 3 C CH 3 H 2 O + H 3 C CH 3 O H eq = 0.002
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O O H K = 2000 Chloral hydrate Cl 3 C H H 2 O + Cl 3 C H O H eq O H F 3 C CF 3 O H 2 O + F 3 C CF 3 O H K eq = 1,200,000 Electron Withdrawing Groups destabilize carbonyl
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