Question

1. Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of 2-bromobutane in 2 mL of 1% AgNO, in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 ml of 1% AgNO, in ethanol. a. list the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. b. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor Sylor Sw2 mechanisms. 2. Two separate reactions are conducted as outlined below. Reaction 1: 4 drops of benzyl chloride in 2 mL of 1% AgNO, in ethanol. Reaction 2: 4 drops of 2-chlorobutane in 2 mL of 1% AgNO, in ethanol. a List the expected rate of each of the reactions. List the slowest reaction first and fastest reaction last. b. Explain your reasoning based on substrate structure, the nature of the leaving group (if applicable), and whether the conditions favor S1 or 5x2 mechanisms. (NOTE: carefully consider the available resonance structures for each of the substrates, le, which forms the more stable carbocation?).

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Answer 1

(a) rate of sin = k [2-chlorobutane (slower) rate of ren = k [2-bromobutaine (fastest) (6) The reaction conditions favoro snt mechanism. Be is better leaving group compared to ce. So rate of 2 brondbutine is faster than 2-chlorobutane. state of Rxn = k [2-chlosobutane slower) rate ofron = k [benzylchloride (fastest) 6. The reaction conditions farors sud mechanism. leaving group (ce] is same in both substates. & Aged relatively stable carbocation) due to resonance + N + Ayet 120 Carbocastion) stability, oreler