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See Poster TH 7 th floor hallway!. Help Needed! at ACS Family Science Night at Oak Grove Middle School, Concord Wednesday, Oct.22, 6 - 9 pm. What would you do? Help set up experiments Help middle school students (and their parents) do the experiments. What would you get?
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See Poster TH 7th floor hallway! Help Needed!atACSFamily Science Night at Oak Grove Middle School, Concord Wednesday, Oct.22, 6 - 9 pm • What would you do? • Help set up experiments • Help middle school students (and their parents) do the experiments • What would you get? • experience in working with youngsters and showing them the fun of science (chemistry!) • a nice entry on your resume • a good impression with your instructor! Please email msequin@sfsu.edu if you can help! It’s fun!
Today: • Diels-Alder (cont.) • Esterification (Exp.5) a first introduction D.-A. adduct
Diels – Alder Reactions (Exp.4) Diels-Alder reactions are another example of syntheses that introduce additional C – C bonds to a reactant. Which structural feature is always formed as the result of Diels-Alder reactions? Diels-Alder reactions are what type of reactions? A cyclohexene ring. A stereospecific reaction, s-cis addition
Diels – Alder Reactions The Diels-Alder reaction requires a 1,3-diene and a dienophile. 1,3-diene in s-cis conformation Dienophile: alkene, most reactive if EWG is attached
Diels – Alder Reactions The Diels-Alder reaction requires a 1,3-diene (in s-cis) and a dienophile (alkene, best with EWG attached). Reaction equations for our experiment: Retro Diels Alder:Cracking of dimer Diels Alder: Reaction of 1,3-cyclopentadiene with maleic anhydride Hydrolysis of Diels-Alder product Dimer D.-A. adduct Cis endo • Compare: • Polarity of I versus II • Mp. of I versus II
Diels – Alder Reactions Which of the following dienes would be most reactive? why? 1,3-cyclopentadiene, 1,3-butadiene (see problems on Report Form) Which of the following dienophiles would be more reactive? Ethene or maleic anhydride
Diels – Alder Reactions Synthesis of Natural Products D C A B Steroids
CH3 CH3 D C CH3 CH3 A B HO Cholesterol
Diels Alder The H-NMR of the dimer of 1,3-cyclopentadiene is quite complex, with many signals. In contrast, the proton NMR of our Diels-Alder product is simple, with few signals; the same is true for its hydrolysis product. How can you explain this?
Methyl Benzoate Synthesis You will heat your reaction under reflux for 1 hour! Do Practice Problems, calculations … • In order to increase the yield of the ester, which of the following would help? • use an excess of methanol • use an excess of conc. sulfuric acid • Calculations …! Why sulfuric acid and not HCl?
Esters and Esterifications • General properties of esters? • Compare the boiling points of carboxylic acids and esters of similar molecular weight and explain. • Examples of esters in biological systems? • Fats and Oils • Waxes • Ripening process in fruits • phosphate esters in DNA
Salicin and Aspirin Salicin in willow bark (Salix)
Next time: Conclusion of “Esterification” (Exp. 5) Grignard reactions (Exp. 6)