Test answers 7 9 a the following reaction produces a

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Test – ANSWERS 7 9. a. The following reaction produces a major and a minor product. Give a mechanism to explain the formation of each product. (3 points) b. Identify the major product. (1 point) c. Justify your choice. (1 point) O H + OH Ph O H O H O H OH Ph OH Ph O Ph O H :B (eg: conjugate base of the acid) O Ph O H :B (eg: conjugate base of the acid) O Ph O O Ph O Major: the carbocation is resonance-stabilized No resonance- stabilization of the carbocation Minor pathway Major Minor 1 (the resonance structure must be shown) Mechanism: - Perfectly drawn: 3/3 - Correct idea but errors made: 2/3 - A reasonable step is drawn but the basic idea is missing: 1/3 - Incorrect/missing mechanism: 0/3 1
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Test – ANSWERS 8 BONUS! Give a complete mechanism for the following transformation. (2 points) OH Me Me H 2 SO 4 O S OH O O H OH 2 Me Me Me Me H H O S OH O O Me Marking: 2/2: perfect 1/2: main idea but with 1-2 minor errors 0/2: incorrect or >2 minor errors
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