326: Organic Chemistry - Study Guide
326: Organic Chemistry - Study Guide 326
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This 2 page Study Guide was uploaded by Andrew Ghobrial on Wednesday October 15, 2014. The Study Guide belongs to 326 at Stony Brook University taught by Prof. Fowler in Fall. Since its upload, it has received 197 views. For similar materials see Organic Chemistry in Chemistry at Stony Brook University.
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Date Created: 10/15/14
CHE 326 Studv Guide 13Diene Svntheses Chapter 13 Solomons and Fryhle discusses conjugation and various reactions of 13dienes The reactions include the very important DielsAlder reaction which features the reaction of a 13diene with an alkene to give a cyclohexene ring 30 E An example of a Diels Alder reaction 0 AK In CHE 321 we discussed various ways to make alkenes but we did not discuss methodology for making dienes Fortunately we can apply some of our standard CHE 321 reactions to this important problem 1 Elimination Reactions to give 13 dienes Here are some simple examples VOK NBS 6 CH3 W In A a vinyl Li reagent is added to a ketone to give an alcohol Acid catalyzed elimination will give the most substituted and thus most stable diene In B Free radical bromination at the allylic positions gives a tertiary bromide Elimination with hydroxide gives the most stable diene Elimination with a hindered base gives the most accessible isomer In special circumstances we can make a diene via a double elimination reaction Br 39Br Br Br This works in the case C of cyclohexene because the alternate alkyne product would be too strained But it will not work in an acyclic case D because the preferred product will be the alkyne not the diene ll 2 Dienolates Here is a special synthesis of a diene involving enolate chemistry 7 0 CSiCH33 o 39 E JVW V We know that a ketone is is equilibrium with its enol form 0 OH ax If we add a trimethylsilyl chloride TMSCI and a base like triethylamine NEt3 we can trap the enolate with the TMS group This TMS protecting group can be removed at some later time in a reaction scheme Later in the course we will add additional methods of 13diene synthesis Don t worry about them now 3 Organometallic Coupling Reactions These reactions are discussed in Special Topic H pages 1016 1017 4 Wittig Reaction This reaction is a very useful method of making alkenes it can also be used to make a diene It is discussed in Chapter 16 pages 711715
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