Problem Set 2 Solution

Be sure to include any reasonable resonance

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Unformatted text preview: above, you have access to cyclohexanol. 20 points for a correct synthesis, - 1 for each incorrect step. - 1 for using wrong reagent - 1 for incorrect product of a reaction - 2 for alchemy or reactions not covered in lectures - 2 for miscounting carbon Name Section Rec TA Side 4 of 6 Ch 1b, Problem Set Two Due Friday, Jan. 24, 2014 at 4 PM PST in the Drop Box 7. (15 POINTS) Decarboxylation, the loss of a CO2 group from a molecule, is efficient for certain chemical structures, including 1. a) Draw a structure for X, the product of a decarboxylation reaction on 1 (before acidic work up; HINT: X has a charge). Include the appropriate curved arrows that take you from 1, through an intermediate, and to the final product. Be sure to include any reasonable resonance structures associated with the final product, X. a. b) Explain why compound 2 does not readily undergo an analogous decarboxylation reaction. c) Predict whether 3 should decarboxylate faster or slower than 1 and briefly explain your choice. 3 points correct product (including resonance), 2 points curved arrows b. For full c...
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This document was uploaded on 03/09/2014 for the course CH 1b at Caltech.

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