l16 - Question 22(c) on CHE 321 Final Exam Fall 07 Most...

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Question 22(c) on CHE 321 Final Exam Fall 07 Most missed it When acetone reacts with methyl lithium two products are formed. One is the expected addition product with e negative charge on the electronegative oxygen atom the negative charge on the electronegative oxygen atom. Give the structure of the second product which also has the negative charge on the electronegative oxygen atom. O O CH 3 C CH 3 CH 3 Li CH 3 C CH 3 CH 3 + ? O O O O O Li A B C D E
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Question 22(c) on CHE 321 Final Exam When acetone reacts with methyl lithium two products are formed. One is the expected addition product with e negative charge on the electronegative oxygen atom the negative charge on the electronegative oxygen atom. Give the structure of the second product which also has the negative charge on the electronegative oxygen atom. O O CH 3 C CH 3 CH 3 Li CH 3 C CH 3 CH 3 + ? C C C O H H H H C O H H nolate H H C C H H H Enolate
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Li Lithium diisopropylamide ( LDA ) N Ka 40 Very strong hindered base N +H + N H pKa = 40 How can you favor the enolate formation? Use a strong base that will not act as a nucleophile. C C C O H H H H C O H H LDA pKa = 19 nolate H H C C H H H Enolate
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K eq = 1.5 x 10 -4 Keto Enol These two compounds C O H H C O H
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l16 - Question 22(c) on CHE 321 Final Exam Fall 07 Most...

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