Organic chemistry Assessment

1. Predict the products and mechanisms of the following reactions. When more than one product or mechanism is possible, explain which are most likely.

2. The reaction of an amine with an alkyl halide gives an ammonium salt.

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 will be faster or slower in a more polar solvent.

3. The following below reaction can undergo substitution by both Sand Sy' mechanisms. Since it is a 1" alkyl halide, we expect Ss but not Ss' reactions. Draw a mechanism for the Sy reaction shown below; draw all resonance structure of the intermediate. How can this primary halide undergo Sy reactions? Why is there no competition with E2 or El mechanisms?

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