HW19Key - A good explanation should require no more than 2...

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CH 310M/318M Spring 2007 Last Name: First Name: Dr. Bocknack UTEID: Score: Please circle the section in which you are registered. POINTS MAY BE DEDUCTED IF YOU DON’T! MWF 9:00 TTh 8:00 Graded Homework Problem #19 Deadline : 3:00 p.m., Monday, 4/30/07 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part of this question, two reactions ( A and B ) are listed. Assume that both reactions occur by the same reaction mechanism . First, decide which of the four reaction mechanisms from Chapter 9 is most likely responsible for the observed reactions. Circle your choice. Then, indicate which reaction ( A or B ) is likely to be faster by circling the appropriate letter. Explain your answers in the space provided
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Unformatted text preview: . A good explanation should require no more than 2 or 3 sentences! (a) A : B : I C N Na CH 3 OH solvent N I C N Na DMF solvent N Explanation: (b) A : B : Br CH 3 H 2 O (solvent) CH 3 Cl CH 3 H 2 O (solvent) CH 3 Explanation: S N 1 S N 2 E1 E2 A B S N 1 S N 2 E1 E2 A B Substitution on 1° substrate must occur via S N 2. S N 2 is favored in polar aprotic solvents (like DMF, which cannot form hydrogen bonds to anions) and disfavored in protic solvents (like CH 3 OH, which can form hydrogen bonds to anions), so B should be faster. Elimination on 3° substrate with weak base consistent with E1. A should be faster because Br – is a better leaving group (weaker base) than Cl – ....
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