quiz chpt 11 solutions

quiz chpt 11 solutions - .J I"so J_J 1 CH 383 AY 2007-2008...

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..J I - " so'- J 1"", __ J CH 383 AY 2007-2008 Name --------~ A Hour Date --------- 50 points Quiz Chapter 11 15 Minutes (5) 1. Explain why polar protic solvents slow down SN2 reactions yet are greatly favored in SN 1 reactions. PROTIC SOLVENTS IN S N 2 REACTIONS SOLVATE THE NUCLEOPHILE THUS SLOWING THE REACTION RATE. WHEREAS IN S N 1, THE PROTIC SOLVENTS LOWER THE TRANSITION-STATE ENERGY LEADING TO THE CARBOCATION INTERMEDIATE THUS INCREASING THE RATE. (5) 2. If you triple the concentration of the nucleophile in an SNI reaction what happens to the reaction rate? NOTHING. THE NUCLEOPHILE IS NOT IN THE 1 ST ORDER RATE EQUATION FOR S N 1 REACTIONS. (5) 3. For an E2 reaction, what must be the geometry of the H and X groups (X=leaving group) on the molecule? ANTI PERIPLANAR (5) 4. Circle the most reactive compound in an SN 1 reaction. CI ~ (5) 5. Identify and define the rule that dictates the major product in elimination reactions. ZAITSEV'S RULE: THE MORE HIGHLY SUBSTITUTED ALKENE PRODUCT PREDOMINATES. CH383, AY07-08 Quiz Ch II, A Hour
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-------------- Name: , , CH 383 Quiz 11 A Hour continued (25) 6. Predict the type of reaction that will occur between (S)-3-bromo-2,2-dimethylpentane with 0.10 M Na+-OQCH 3 )J in dilute aqueous ethanol. Support your prediction using the four influencing factors. (Substrate, leaving group, base, solvent) Then draw the mechanism for the reaction to include all lone pair electrons, electron pushing arrows, transition states and intermediates. Name the product(s). Discuss the optical activity of the product(s). ~.l -SUBSTRATE - SECONDARY HALIDE LEAVING GROUP - GOOD BASE - STRONG BASE AND BULKY SOLVENT - PROTIC NAME - TRANS-4,4-DIMETHYL-2-PENTENE NO CHIRAL CENTERS THUS NO OPTICAL ACTIVITY CH383, AY07-08 2 Quiz Ch 11, A Hour
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This note was uploaded on 04/15/2008 for the course CH 383 taught by Professor Comitz during the Fall '08 term at West Point.

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quiz chpt 11 solutions - .J I"so J_J 1 CH 383 AY 2007-2008...

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