14D_w10_e02

14D_w10_e02 - Chemistry 14D Winter 2010 1. Exam 2 Page 1...

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Chemistry 14D Winter 2010 Exam 2 Page 1 Page 1 score = 1. (2) Circle the best statement of Markovnikov’s rule. (a) When HX adds to an alkene, the hydrogen of HX becomes bonded to the alkene carbon that bears the least number of hydrogen atoms. (b) When HX adds to an alkene, the hydrogen of HX becomes bonded to the alkene carbon that bears the greatest number of hydrogen atoms. (c) An addition reaction to an alkene always proceeds through the most stable carbocation. (d) Addition of HX to an alkene gives the least sterically hindered product. 2. (2) Which of the following is the correct mechanistic rationale for Markovnikov’s rule? Circle one: Steric effects Resonance Carbocation stability Leaving group Solvent polarity 3. (5) For each reaction, circle “Yes” if the reaction follows Markovnikov’s rule, and “No” if it does not. For the reactions that do obey Markovnikov’s rule, write the major product in the box. (a) 1. BH 3 2. NaOH, HOOH (b) H 2 Pt (c) HC CCH 3 HBr Yes No Yes No Yes No 4. (6) Write the mechanism for the major product of the following reaction. Draw a box around the product. OCH 3 HCl 5. (3) By adding, subtracting, or transmuting no more than three atoms of the nucleophile, rewrite the reaction of question 4 so that it is obviously faster . (Transmute = change an atom of one element into an atom of another element, i.e., lead into gold.) Do not include the reaction mechanism
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14D_w10_e02 - Chemistry 14D Winter 2010 1. Exam 2 Page 1...

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