Chapter 6 Discussion Section Problems

Chapter 6 Discussion Section Problems - mechanism for each...

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Chapter 6 Discussion Section Problems 1. Predict the compound in each pair that will undergo the S N 2 reaction faster. 2. Show how each compound might be synthesized by the S N 2 displacement of an alkyl halide. 3. Predict the products of the following S N 2 reactions. 4. CHALLENGE: when (±)-2,3-dibromobutane reacts with potassium hydroxide some of the products are (2S,3R)-3-bromo-2-butanol and its enantiomer trans-2-bromo-2-butene. Give mechanisms to account for these products. 5. CHALLENGE: Protonation converts the hydroxyl group of an alcohol to a god leaving group. Suggest a
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Unformatted text preview: mechanism for each reaction. 6. CHALLENGE: The reaction of an amine with an alkyl halide gives an ammonium salt. The rate of this SN2 reaction is sensitive to the polarity of the solvent. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. Consider the nature of the transition state and explain why this reaction should be sensitive to the polarity of the solvent. Predict whether it would be faster or slower in a more polar solvent....
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