Effect of Solvent Measure 2 mL of a 0.1 M solution of silver nitrate in ethanol

Question

Effect of Solvent

Measure 2 mL of a 0.1 M solution of silver nitrate in ethanol in a clean, dry test tube and 2 mL of a 0.1 M solution of silver nitrate in 5% ethanol/95% acetone in another clean, dry test tube. At the same time, add 1 drops of 2-chloro-2-methylpropane to the each test tube. Record the times required for a precipitate to form.

Order the reactivity of the compounds evaluated in the "Effect of Solvent"

experiment? Were these results consistent with the expected results? Discuss

why your results were or were not in agreement with the expected results.

0.1 M solution of silver nitrate in ethanol         4.5 seconds until precipitate formed

0.1 M solution of silver nitrate in 5% ethanol/95% acetone    4.5 seconds until precipitate formed.
  

Explanation / Answer

Alkyl Halide Classification Tests

Qualitative tests for alkyl halides are useful in deciding whether the compound in question is a primary, secondary, or tertiary halide. In general it is quite difficult to prepare solid derivatives of alkyl halides, so we limit this discussion to the two qualitative tests.

(A) the reaction with alcoholic silver nitrate solution and

(B) the reaction with sodium iodide in acetone.

You are to run tests A & B on the following compounds:

1-Bromobutane,

2-Bromobutane,

2-Bromo-2-methylbutane,

1-Chlorobutane

2-Chlorobutane

2-Chloro-2-methylbutane

A. Alcoholic Silver Nitrate If a compound is known to contain a halogen (bromine, chlorine, or iodine), information concerning its environment may be obtained from observation of its reaction with alcoholic silver nitrate. The overall reaction is shown in the following equation:

  Ethanol

RX + AgNO3 ---------------> AgX + RONO2

Such a reaction will be of the SN1 type.

EXPERIMENTAL

Test

                                        acetone

                     RCl + NaI ------------> RI + NaCl

                                        acetone

                     RBr + NaI ------------> RI + NaBr   

EXPERIMENTAL

Test B

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