jan_25 - 1/26/2010 Learning Goals for Organic Chemistry...

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Unformatted text preview: 1/26/2010 Learning Goals for Organic Chemistry Knowledge The structural language of organic chemistry. Reaction mechanisms, the curved arrow formalism. Thermodynamics and kinetics. Spectroscopy. The role of chemistry in nature, technology and addressing contemporary societal problems. A course for those planning more studies in chemistry http://www.ic.sunysb.edu/Class/che326ff/ Skills Problem solving The use of the knowledge of organic chemistry to solve specific problems. Learning to work as a member of a team to solve specific problems in chemistry. Give a mechanism for the following reaction (321 final). How did you do on this problem? A. perfect B. minor error C. some credit D. 0 Give a mechanism for the following reaction (321 final). Which atom has the highest probability of protonation? A. oxygen B. carbon C. hydrogen What are the structures of the rearrangement products? O O Why are these particularly cations good choices? O O carbocation rearrangement C C H H O H O O H H O H H O O O C C CC more stable O H H H O H O H 1 1/26/2010 Conjugated Unsaturated Systems. H H C H H H H C C H H H C C H H C H H C C H H C H C H C H H C H Conjugated Unsaturated Systems. H H C H C H H C H H C C H H C H O C H C H H H O C C H H H H H H H H C C C C C C H H H H H H H H C C C H C H H H H C H C C H H H H C H C C H H H H O C H C C H H H C C H H H H C H C C H H H H C H C C H H Predict the major product of the chlorination of propene. C H + Cl Cl C Cl + H Cl C H + Cl Cl C H + Cl Cl Cl C Cl + H Cl What is a chlorination reaction? How many products are possible from this reaction? Cl Cl hν slow H C + Cl fast C + Cl Cl H H C H C C H H H Cl hν Cl Cl C H H C C H H H H C Cl H C C H H H H C H Cl C C H H H H C H H C C H Cl H H C H H C C H H H Cl hν Cl Cl C H H C C H H H H C Cl H C C H H H H C H Cl C C H H H H C H H C C H Cl H A B C D A=1 B=2 C=3 D=4 E=5 F=6 What is the mechanism of this substitution reaction? A SN1 B SN2 C free radical Why are the C-H bonds adjacent to the double bond weak? C H + Cl Cl C H + Cl Cl Cl C Cl + H Cl BDE = 423 kJ/mol Cl Cl hν slow H C + Cl fast C + Cl Cl Cl BDE = ~465 kJ/mol H H B H C C H C C H H Cl hν Cl Cl C H H C C H H H H C Cl H C C H H H H C H Cl C C H H H H C H H C C H Cl H H C H H C BDE = 369 kJ/mol H H Cl H C H H C C H H H C H H C C H H Cl Cl H C H H C C H Cl H A H D H C H What is the mechanism of this substitution reaction? Which is the weakest C-H bond? H H C H C C H H H Cl C H H C C H H H 2 1/26/2010 Give an explanation for these observations. Exchange your clicker and answer with a friend next to you. Cl O Et 1O Cl Et O Et 1O Et Cl HO Et O 1 Et + O Cl Et 2 HO Et O 1 Et + O Et 2 What type of reaction are these? What are the mechanisms for substitution reactions? What is the difference between these reactions? Substitution. SN1 and SN2 the nucleophile Grade your friends paper. (A, B, C, D and F) What are the mechanisms of these substitutions? Cl O Et + Cl 1O Et Cl O Et + Cl 1O Et SN2 HO Et SN2 HO Et Cl + O 1 -H Et SN1 O Cl Et 2 + O 1 -H Et SN1 O Et 2 -H H O Et Et + Cl H O Et Et + Cl H O Et HO Et HO HO What are the mechanisms of these substitutions? Grade your friends paper. (A, B, C, D and F) Cl O Et + Cl 1O Et Cl O Et + Cl 1O Et SN2 HO Et SN2 HO Et Cl + O 1 -H Et SN1 O Cl Et 2 -H + O 1 -H Et SN1 O Et 2 -H H O Et Et H O Et HO Et + Cl H O Et Et H O Et HO Et + Cl HO HO 3 1/26/2010 A = completely correct, B = minor error, C = major error, D = anything correct and F = nothing correct Cl O Et + Cl 1O Et Students whose University ID numbers end with the selected number will turn in their answers for grading Cl O Et + Cl 1O Et SN2 HO Et SN2 HO Et Cl + O 1 -H Et SN1 O Cl Et 2 -H + O 1 -H Et SN1 O Et 2 -H H O Et Et H O Et HO Et + Cl H O Et Et H O Et HO Et + Cl HO HO Which Which hydrogen is the most acidic in the following compound? The most acidic hydrogen will form the most stable anion. H A A + H Working with your neighbors, draw the anions resulting from the ionization of each of these hydrogens. That is, one of you do H-A and H-B and H-C. Compare your answers. O H H H H B H H A C 4 ...
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