Question

SN2 Reactions of Alkyl Halides

1.a) Which alkyl bromide reacted fastest with sodium iodide in acetone: 1-bromobutane, 2-bromobutane or 2-bromo-2-methylpropane?

b) Which alkyl bromide reacted slowest? Explain how the structure of the alkyl halide affects the rate of an SN2 reaction.

2. a)Which alkyl bromide reacted faster with sodium iodide in acetone: 1-bromobutane or 1-bromo2,2-dimethylpropane (neopentyl bromide)?

b)Both of these are primary halides. Why was there a difference in reactivity?

3.a)Which halide reacted faster with sodium iodide in acetone: 1-bromobutane or 1-chlorobutane?

b) Explain how the nature of the leaving group affects the rate of an SN2 reaction. Would 1-iodobutane react faster or slower than the other halides?

c) How would we know that the reaction took place? Explain.

4. Write balanced equations for all substitution reactions that took place between the alkyl halides and NaI. Propose intermediates or transition states for each reaction.

Answer 1