Chem 230L Laboratory Report Reactivity of Some Alkyl Halides

Experiment # 21 Reactivity of Some Alkyl Halides

I. Introduction:
To understand the reactivity of alkyl halides in nucleophilic substitution reactions (under
both S
N
1 and S
N
2 and conceptualize the fact that the reactivity depends on reaction conditions
and substrate structures.
In the first part of this lab we will explore the reactivity of alkyl halides in nucleophilic
substituitoin reactions through sodium iodide or potassium iodide in acetone. We will see that a
reagent composed of sodium iodide or potassium iodide dissolved in acetone is useful in
classifying alkyl halides according to their reactivity in an S
N
2 reaction. The iodide ion is an
excellent nucleophile, while acetone is a nonpolar solvent. The tendency to form a precipitate
increases the completeness of the reaction. Sodium iodide and potassium iodide are soluble in
acetone but the corresponding bromides and chlorides are not soluble. This means that as the
chloride and bromide ions are produced, the ions are precipitated from the solution. This drives
the equilibrium of the reaction to the right due to Le Chateliers Principle.
In the second part of this lab we will see how a reagent composed of silver nitrate
dissolved in ethanol is useful in classifying alkyl halides according to their reactivity in S
N
1
reactions. This process is very similar to the process above as the precipitate causes the reaction
to be enhanced. In this reaction, the nitrate ion is a poor nucleophile while the 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. This precipitate allows the reaction to go to completion.

II. Procedure:
Part A:
-Label a series of ten clean and dry test tubes from 1 to 10 (10X75 test tubes may be used)
-Place 2 mL of a 15% NaI-in-acetone solution into each test tube.
-Add 4 drops of one of the following halides to the appropriate test tube:
- (1) 2-chlorobutane
- (2) 2-bromobutane
- (3) 1-chlorobutane
- (4) 1-bromobutane
- (5) 2-chloro-2-methylpropane (t-butyl chloride)
- (6) crotyl chloride
- (7) benzyl chloride
- (8) bromobenzene
- (9) bromocyclohexane
- (10) bromocyclopentane
-Avoid cross contamination of these compounds by ensuring the fact that you place the dropper
in the appropriate container after using it.
-After adding the halide, shake the tube adequately so that the alkyl halide and the solvent mix
well.
-Then record the times needed for any precipitate or cloudiness to form.
-After about 5 minutes, place any test tubes that do not contain a precipitate in a 50 degree
Celsius water bath. Do not allow the temperature of the water bath to exceed 50 degree Celsius
because the acetone will evaporate or boil out of the test tube.
-After about 1 minute of heating, cool the test tubes to room temperature and note whether a
reaction has occurred. (Generally, reactive halides give a precipitate within 3 minutes at room
temperature)
-Record all your results in your notebook.
Part B:
-Label a series of ten clean and dry test tubes from 1 to 10.
-Add 2mL of a 1% ethanolic silver nitrate solution to each tube tube.
-Add 4 drops of the appropriate halide to each test tube, using the same numbering method as the
sodium iodide test.
-Make sure to avoid cross-contamination.
-After adding the halide, shake the test tube well to ensure adequate mixing of the alkyl halide
and the solvent.
-After mixing the samples, record the times needed for any precipitate or cloudiness to form.
-Record your results
-After about 5 minutes, place any test tubes that do not contain a precipitate or cloudiness in a
hot water bath at about 100 degrees Celsius.
-After about 1 minute of heating, cool the test tubes to room temperature and note/record
whether a reaction has occurred. (Generally, reactive halides give a precipitate within 3 minutes
at room temperature.
-Record all results in notebook.

III. Observations







(1) 2-chlorobutane


(2) 2-bromobutane


(3) 1-chlorobutane


(4) 1-bromobutane


(5) 2-chloro-2-
methylpropane (t-
butyl chloride)


(6) crotyl chloride


(7) benzyl chloride


(8) bromobenzene


(9)
bromocyclohexane


(10)
bromocyclopentane






IV. Conclusions