Question

In this lab you will explore the effect structure has on the rate of SN2/ SN1 reactions. The substances to be testedare listed below

1)1-chlorobutane (2) 1-bromobutane
(3) 2-chlorobutane (4)2-bromobutane(5) 2-chloro- 2-methylpropane (6) 2-bromo- 2-methylpropane(7) 1-bromo- 2-methylpropane (8) bromocyclohexane(9) bromobenzene (10) ß-Bromostyrene (11) 2-iodobutane

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General Procedure: In each test, add 5 drops of haloalkane to a test-tube, and then add 1 mL of solution (1M NaI/acetone for the SN2reactions reactions). Mix by swirling vigorously. Record the time it takes to see a precipitate.

3. What was the effect of the halide being directly attached to an aryl/vinyl carbon on the SN2reactivity? Which compounds are they? Did your observations agree with what you learned in class?
(b) What was the effect of the halide being directly attached to an aryl/vinyl carbon on the SN1reactivity? Did your observations agree with what you learned in class?

4. Both 1-bromobutane and 1-bromo- 2-methylpropane are primary bromides. Can you explain thedifference in their SN2 reactivity, if there was any?

5. What would be the specific mathematical effect on the reaction rate if you carried out thesodium iodide-in-acetone reactions on the alkyl halides using an iodide solution half asconcentrated? (“Slower” or “faster” is not specific enough.)