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11 Dec 2019

A. Arrange the organic halides below in order of decreasing experimental reactivity toward iodide ion (NaI in acetone).

B. Are there significant differences in the bromides and chlorides?

C. What structural change correlates with reactivity in this mechanism (it should be SN2, right?)?

Please explain answers! Thank you!

halide reagents:

1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane, benzyl chloride, 2-bromo-2-methylpropane, chlorobenzene, bromobenzene, 2-chloro-2-methylpropane

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13 Dec 2019

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In organic chem lab Reactivities of alkyl halides, write the structure and identify the structural type (primary, secondary, tertiary, aryl and benzyl) for each of the known halides you are using in part A & B of this experiment. The unknown halides are listed in the experimental procedures section below.

1-chlorobutane

1-bromobutane

2-chlorobutane

2-bromobutane

2-chloro-2-methylpropane

2-bromo-2-methylpropane

chlorobenzene

bromobenzene

benzyl chloride

benzyl bromide

Describe in detail how you will know when a reaction occurs in both Part A & B of this experiment? Describe how a positive result in Part A is different from a positive result in Part B?

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) Ã-Bromostyrene (11) 2-iodobutane

.
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? (âSlowerâ or âfasterâ is not specific enough.)

Questions:

1) In the tests with sodium iodide in acetone and silver nitrate in ethanol, why should 2-bromobutane react faster than 2-chlorobutane?

2) Why is benzyl chloride reactive in both tests, whereas bromobenzene is unreactive?

3) When benzyl chloride is treated with sodium iodide in acetone, it reacts much faster than 1-chlorobutane, even though both compounds are primary alkyl chlorides. Explain this rate difference.

4) 2-Chlorobutane reacts much more slowly than 2-chloro-2-methylpropane in the silver nitrate test. Explain this difference in reactivity.

5) Bromocyclopentane is more reactive than bromocyclohexane when heated with sodium iodide in acetone. Explain this difference in reactivity.

CHEM 211 Biological Chemistry Lab #8-Factors effecting the reactions of alkylhalides A. Experimental objectives Examine the effects of leaving group, alkyl group structure and solvent polarity on the reaction of alkyl halides Examine the effects of solvent polarity on the reaction of a tertiary alkyl halide with sodium hydroxide To examine SN1 and SN2 reaction conditions To learn the most two important factors that effects the reactivities of alkyl halides in nucleophilic substitution reaction B. Introduction The reactivities of alkyl halides in nucleophilic substitution reactions depend on two important factors: reaction conditions and substrate structure. The reactivities of the several substrate types will be examined under both SN1 and SN2 reaction conditions in this experiment A reagent composed of sodium iodide or potassium iodide dissolved in acetone is useful in classifying alkyl halides according to their reactivity in an SN2 reaction. Iodide is an excellent nucleophile, and acetone is a nonpolar solvent. Thetendency to form a precipitate increases the completeness of the reaction. Sodiumiodide and potassium iodide are soluble in acetone, but the corresponding bromidesand chlorides are not soluble. Consequently, as bromide ion or chloride ion is produced, the ion is precipitated from the solution. According to LeChatelier' s Principle, the precipitation of a product from the reaction solution drives the equilibrium toward the right such is the case in the reaction described here R-Cl Na RI NaCl (s) R-Br Na RI-NaBr (s) A reagent composed of silver nitrate dissolved in ethanol is useful in classifying alkyl halides according to their reactivity in an SN1 reaction. Nitrate ion is a poor nucleophile and ethanol is a moderately powerful ionizing solvent. The silver ion, because of its ability to coordinate the leaving halide ion to form a silver halide precipitate ,greatly assists the ionization of the alkyl halide. Again a precipitate as one of the reaction products also enhances the reaction C2H5OH R OC2H5 CI Ag AgCl (s) Page 1 of 5

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