CHM 151 (PS 8 F07)

CHM 151 (PS 8 F07) - 3 4 Consider this reaction CH 3 CH 2...

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CHEMISTRY 151L.001 Fall 2007 Problem Set 7 1. Identify whether each of the following molecules would most likely react as the nucleophile or electrophile in an S N 1 or S N 2 substitution reaction. Identify the nucleophilic or electrophilic ATOM in each. Also, identify any good leaving groups. Cl Br O H OTs KI H 2 O Cl PhSNa Et 2 NH Cl HC CNa 2. Predict the substitution products of the following reactions and pay attention to stereochemistry. a. Cl H EtOH b. Cl H NaSCH 2 CH 3 H 3 C S O CH 3
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CHM 151L.001; Problem Set 7 2 3. Draw energy diagrams for the two substitution reactions shown below. Show clearly the T.S. structure and activation energy of the rate determining step and the Δ G of the reaction. Which reaction would you expect to occur faster? Cl NaI H 3 C O CH 3 I + NaCl Cl NaI H 3 C O CH 3 I + NaCl
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CHM 151L.001; Problem Set 7
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Unformatted text preview: 3 4. Consider this reaction: CH 3 CH 2 CH 3 Br + – OH H 2 O [ ! ] = +22 o H CH 3 CH 2 CH 3 H OH a. What is the expected effect on the rate of the reaction if each of the following changes is made? Possible answers: increases, decreases, remains the same. Change Effect on S N 1 Effect on S N 2 Use 2-methyl-2-bromobutane- instead of 2-bromobutane. Use the alkyl iodide instead of the alkyl bromide Use H 2 O (only) instead of – OH and H 2 O Increase concentration of – OH Change solvent to DMSO b. Which of the characterization techniques that you have learned about so far would best help you to distinguish whether this substitution product was a result of the S N 1 versus S N 2 mechanism? Explain your answer....
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