Nucleophilic Substitution

Part 1: Studying S_N1 Reactions

Alkyl Halide Structure:

1. Measure 2 mL of a 0.1 M solution of silver nitrate in absolute ethanol into each of the three test tubes.
2. Add 2 drops of 1-bromobutane into the first test tube. Add 2 drops of 2-bromobutane into the second test tube.
3. Add 2 drops of 2-bromo-2-methylpropane into the final, third test tube.
4. Stopper and shake each test tube.
5. Note the time at which the first signs of cloudiness or precipitate appears.

Leaving Group Effects:

1. Measure 2 mL of a 0.1 M solution of silver nitrate in absolute ethanol into each of the two test tubes.
2. Add 2 drops of 2-bromo-2-methylpropane into the first test tube and 2 drops of 2-chloro-2-methylpropane into the second test tube.
3. Stopper and shake each test tube.
4. Note the time at which the first signs of cloudiness or precipitate appears.

Solvent Polarity Effects:

1. Measure 2 mL of a 0.1 M solution of silver nitrate in absolute ethanol into the first test tube and measure 2 mL of a 0.1 M solution of silver nitrate in 5% ethanol/95% acetone into the second test tube.
2. Add 2 drops of 2-bromo-2-methylpropane into both test tubes.
3. Stopper and shake each test tube.
4. Note the time at which the first signs of cloudiness or precipitate appears.

Determining the S_N1 Rate Law:

1. Measure 0.5 mL of a 0.1 M solution of 2-chloro-2-methylpropane in ethanol into the first test tube.
2. Measure 0.5 mL of a 0.2 M solution of 2-chloro-2-methylpropane in ethanol into the second test tube.
3. Add 1.0 mL of a 0.1 M solution of silver nitrate in absolute ethanol into both test tubes.
4. Carefully measure the time it takes to observe cloudiness or precipitation.
5. Measure 1.0 mL of a 0.1 M solution of silver nitrate in ethanol into the third test tube.
6. Into the fourth test tube, measure 0.5 mL of a 0.1 M solution of silver nitrate in ethanol and add an additional 0.5 mL of ethanol.
7. Into both test tubes, add 1.0 mL of 0.1 M 2-chloro-2-methylpropane in ethanol and carefully measure the time it takes to observe cloudiness or precipitation.

Part 2: Studying S_N2 Reactions

Alkyl Halide Structure:

1. Measure 2 mL of 15% sodium iodide in acetone into each of the three test tubes.
2. Add 2 drops of 1-bromobutane into the first test tube.
3. Add 2 drops of 2-bromobutane into the second test tube.
4. Finally, add 2 drops of 2-bromo-2-methylpropane into the final, third test tube.
5. Stopper and shake each test tube.
6. Note the time at which the first signs of cloudiness or precipitate appears.

Steric Effects:

1. Measure 1 mL of 15% sodium iodide in acetone solution into each of the two test tubes.
2. Add 2 drops of 1-bromobutane into the first test tube and add 2 drops of neopentyl bromide into the second test tube.
3. Stopper and shake each test tube.
4. Note the time at which the first signs of cloudiness or precipitate appears.

Leaving Group Effects:

1. Measure 1 mL of 15% sodium iodide in acetone solution into each of the two test tubes.
2. Add 2 drops of 1-bromobutane into the first test tube and add 2 drops of 1-chlorobutane into the second test tube.
3. Stopper and shake each test tube.
4. Note the time at which the first signs of cloudiness or precipitate appears.

Determining the S_N2 Rate Law:

1. Measure 1.0 mL of 15% sodium iodide in acetone solution into two test tubes.
2. Add 0.1 mL of 1.0 M solution of 1-bromobutane in acetone into the first test tube.
3. Carefully measure the time it takes to observe the first sign of cloudiness.
4. Into the second test tube, add 0.1 mL of a 2.0 M solution of 1-bromobutane in acetone.
5. Carefully measure the time it takes to observe the first sign of cloudiness.
6. Measure 1.0 mL of 1.0 M 1-bromobutane in acetone into the third and fourth test tubes.
7. Add 0.1 mL of a 7.5 % sodium iodide in acetone solution into the third test tube.
8. Carefully measure the time it takes to observe the first sign of cloudiness.
9. Into the fourth test tube, add 0.1 mL of a 15% sodium iodide in acetone solution and carefully measure the time it takes to observe the first sign of cloudiness.