Chem E2a-Lecture 6-Annotated-2013 - Chem E 2a Lecture 6 Chapters 7 21 While Youre Wai:ng for Lecture to Start Determine the major organic product for

Chem E2a-Lecture 6-Annotated-2013 - Chem E 2a Lecture 6...

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Chem E-­‐2a Lecture 6 Chapters 7 & 21
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While You re Wai:ng for Lecture to Start Determine the major organic product for each of the following reactions: Br + CN Br + OH Br + H 2 O + OH Br + CH 3 OH Br + H 2 SO 4 OH 1
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Making Alcohols Leave: Part 1 -­‐ Using Acid Explain why the following reaction is not effective: We can convert an alcohol into a good leaving group by protonating the alcohol in strong hydrohalic acids. Let s see how this works: Reading : Section 7.4f OH NaBr Br does NOT work conc. HBr OH Br conc. HI OH I 2
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Strong acids are not always useful for converting alcohols into good leaving groups. What is the problem with each of the following reactions? Making Alcohols Leave: Part 2 – Problems with Acid conc. HBr OH Br does NOT work OH conc. HCl Cl does NOT work 3
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A better way to convert an alcohol to a good leaving group is to convert it into a sulfonate ester ; a specific example is a p -toluenesulfonate, usually just called a tosylate : Making Alcohols Leave: Part 3 -­‐ Using Sulfonates A tosylate is an excellent leaving group! Another example is a trifluoromethanesulfonate, usually just called a triflate : OH OTs TsCl = S CH 3 Cl O O pyridine = N Reading : Section 7.4f 4
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