Title: Synthesis of t- Pentyl Chloride by unimolecular nucleophilic substitution

Objective: To convert t-pentyl alcohol to tert-pentyl chloride using Sn1 reaction with HCl.

Materials required: Conical bottom flasks, Erlenmeyer flasks, Condenser, receiver distilling
still, hot plate, Pasteur pipette , graduated cylinder, separatory funnel, and stirring rod.

Chemicals required: t-pentyl alcohol, concentrated hydrochloric acid, sodium chloride solution,
5% sodium carbonate solution, silver Nitrate solution.

Procedure:

1. Place 3 mL t-pentyl alcohol into a conical flask, which will be flask 1.

2. Slowly add 7.5 mL of concentrated hydrochloric acid by stirring the mixture.

3. Transfer the mixture to a separatory funnel to get two layers.

4. Dispose the lower layer and add 3 mL deionized water to wash t-pentyl chloride.

5. Add 2 mL sodium chloride, and then add 2 mL of 5% NaHCO₃ to t-pentyl chloride.

6. Again, dispose lower layer and filter the upper layer using a Pasteur pipette.

7. Distill the filtrate.

8. Test the distillate with AgNO₃, if it gives a white precipitate, then the solution is pure.

Results and Data:

After adding concentrated hydrochloric acid Two layers formed, which was then separated.

After distillation and addition of AgNO₃ After distillation a clear solution, and after
adding silver nitrate, a white precipitate
formed.

Discussion:

Alkyl halides can be prepared by acid catalyzed substitution reactions of alcohols, and SN1, SN2
are pathways that compounds follow. Secondary alcohols react with hydrogen halides by SN1
and SN2 mechanism; primary alcohols follow SN2 and tertiary alcohol follow SN1 mechanism.
In SN1 mechanism, the rate determining step is where the alcohol gets protonated, by water loss,
and the second step would be attach of the nucleophile on the carbocation. In this experiment we
converted tert-pentyl alcohol to tert- pentyl chloride using a SN1 reaction with HCl. Depending
on the reagents alcohols are paired with, they can function as an acid, base, nucleophile or
electrophile, in this experiment when a halloacid such as HCl is used, the reaction would favor a
substitution role. When the alcohol is protonated by HCl the chloride ion forms a conjugate base,
and it is performed as a SN1 reaction because of a tertiary alcohol, which will form a oxonium
ion. The oxonium ion, reacts to form a stable tertiary carbocation, then the chloride ion from HCl
reacts with the carbocation to give tertiary chloride. Sodium carbonate and water were used to
remove unreacted HCl, and was done quickly to prevent hydrolysis of the product back to
alcohol.

Reaction mechanism:

Conclusion:

In conclusion, upon testing my distillate with silver nitrate, a white precipitate had formed from a
clear solution, indicating that the distillate was pure t-pentyl chloride.
The silver nitrate test is sensitive to detect small concentrations of halide ions, and various
precipitates may form from the reaction between silver and halide ions, i.e a white precipitate
indicates a chloride ion.