Discuss the Sn1 mechanism and then summarize how the different conditions impacted the rate. Look at leaving group, solvent, and substitution. What trends did you observe? Did any of the results turn out differently than you had expected? Do you think this is because of the mechanism or because of practical issues? Suggest possible ways to improve on the rate study for future trials.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Discuss the Sn1 mechanism and then summarize how the different conditions impacted the rate. Look at leaving group, solvent, and substitution. What trends did you observe? Did any of the results turn out differently than you had expected? Do you think this is because of the mechanism or because of practical issues? Suggest possible ways to improve on the rate study for future trials.

Leaving Group Effect:
Prepare two 20 mL portions of 50% isopropyl alcohol in water in 50 mL Erlenmeyer flasks. To
each flask, add 3 drops of phenolphthalein solution (prepared in ethanol) and EXACTLY 3 drops
of 0.5 M NAOH. Swirl each flask.
Add EXACTLY 2 drops of 2-bromo-2-methylpropane to one flask, recording the time of
addition. Swirl constantly until the color changes from pink to colorless. Record the time when
the color changes. If the color does not change in 5 minutes, allow the flask to sit on the
benchtop, swirling occasionally.
Add EXACTLY 2 drops of 2-chloro-2-methylpropane to the other flask, recording the time of
addition. Swirl constantly until the color changes from pink to colorless. Record the time when
the color changes. If the color does not change in 5 minutes, allow the flask to sit on the
benchtop, swirling occasionally.
Alkyl Group Effect:
Prepare one 20 mL portion of 50% isopropyl alcohol in water in a 50 mL Erlenmeyer flask. Add
3 drops of phenolphthalein solution to the flask and then add EXACTLY 3 drops of 0.5 M
NaOH. Swirl the flask.
Add EXACTLY 2 drops of 2-bromopropane to the flask, recording the time of addition. Swirl
constantly until the color changes from pink to colorless. Record the time when the color
changes. If the color does not change in 5 minutes, allow the flask to sit on the benchtop,
swirling occasionally.
Compare the time it takes for this reaction to the time it takes for the reaction of 2-bromo-2-
methylpropane from above (part 1).
Solvent Polarity Effect:
Prepare one 20 mL portion of 40% isopropyl alcohol in water in a 50 mL Erlenmeyer flask. Add
3 drops of phenolphthalein solution to the flask and then add EXACTLY 3 drops of 0.5 M
NaOH. Swirl the flask.
Add EXACTLY 2 drops of 2-bromo-2-methylpropane to the flask, recording the time of
addition. Swirl constantly until the color changes from pink to colorless. Record the time when
Transcribed Image Text:Leaving Group Effect: Prepare two 20 mL portions of 50% isopropyl alcohol in water in 50 mL Erlenmeyer flasks. To each flask, add 3 drops of phenolphthalein solution (prepared in ethanol) and EXACTLY 3 drops of 0.5 M NAOH. Swirl each flask. Add EXACTLY 2 drops of 2-bromo-2-methylpropane to one flask, recording the time of addition. Swirl constantly until the color changes from pink to colorless. Record the time when the color changes. If the color does not change in 5 minutes, allow the flask to sit on the benchtop, swirling occasionally. Add EXACTLY 2 drops of 2-chloro-2-methylpropane to the other flask, recording the time of addition. Swirl constantly until the color changes from pink to colorless. Record the time when the color changes. If the color does not change in 5 minutes, allow the flask to sit on the benchtop, swirling occasionally. Alkyl Group Effect: Prepare one 20 mL portion of 50% isopropyl alcohol in water in a 50 mL Erlenmeyer flask. Add 3 drops of phenolphthalein solution to the flask and then add EXACTLY 3 drops of 0.5 M NaOH. Swirl the flask. Add EXACTLY 2 drops of 2-bromopropane to the flask, recording the time of addition. Swirl constantly until the color changes from pink to colorless. Record the time when the color changes. If the color does not change in 5 minutes, allow the flask to sit on the benchtop, swirling occasionally. Compare the time it takes for this reaction to the time it takes for the reaction of 2-bromo-2- methylpropane from above (part 1). Solvent Polarity Effect: Prepare one 20 mL portion of 40% isopropyl alcohol in water in a 50 mL Erlenmeyer flask. Add 3 drops of phenolphthalein solution to the flask and then add EXACTLY 3 drops of 0.5 M NaOH. Swirl the flask. Add EXACTLY 2 drops of 2-bromo-2-methylpropane to the flask, recording the time of addition. Swirl constantly until the color changes from pink to colorless. Record the time when
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