CHEM235%20Spr%202004%20Exam%203

CHEM235%20Spr%202004%20Exam%203 - Name: CHEM 235 Organic...

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Name: CHEM 235 – Organic Chemistry Mid-Term Examination 3 This Examination is worth 100 points of your final score of 800. Question 1 (12 points). Explain, with reference to the nature of the reactants and mechanisms of the reactions, the difference in regioselectivity for the products obtained from the following (1 equivalent of the base is used in both reactions) CO 2 Me O 1. NaH/THF/ 0 o C 2. CH 3 I/THF 3. H + /H 2 O, O sole product O 1. LDA/THF, -78 o C 2. CH 3 I O major product O minor product
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Name: Question 2 (12 points). Treatment of methyl hexanoate with a large excess of ethanol and a catalytic amount of sulfuric acid gives ethyl hexanoate. Write the mechanism of this reaction, and describe how you would obtain a higher yield of the ethyl ester.
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Name: Question 3 (8 points) Rank the following compounds in order of increasing acidity: rank the most acidic compound as 1. CH 3 CH 2 OH O H 3 C H 3 C O H 3 C O H O CH 3 H 3 C H 3 C F 3 C O O H O O CH 3 H Question 4 (14 points) Select 4 of the following 6 names or structures.
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CHEM235%20Spr%202004%20Exam%203 - Name: CHEM 235 Organic...

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