Appendix Answers to Questions: 1. Why is it necessary to use cold concentrated HCl? Why is it added in excess?

- The cold concentrated HCl is necessary to prevent alkene formation and to make sure that alkyl halide will be synthesized. The excess addition is for the reaction to reach equilibrium towards the products to produce the alkyl halide. 2. Why is solid NaHCO3 used instead of aqueous NaHCO3. - Solid NaHCO3 prevents hydrolysis of the tert-butyl chloride back to alcohol due to the presence of H2O. 3. Why must the crude alkyl halide product be dried carefully with anhydrous CaCl2 before distillation? - As said in the given notes in the experiment, CaCl2 removes traces of water left in the crude product. Ca2+ forms complexes with many oxygen-containing compounds; therefore it can remove not only water but also unreacted alcohol.

4. What is the purpose of boiling chips? - The boiling chips provide surfaces in which bubbles can form and ensure a constant and equal flow of heat to the sample. 5. Discuss the importance of the continuous flow of water in the condenser during distillation. - The water evaporated due to the heating of the system will pass as steam. If water will not be continuously supplied to flow, the condenser will not be able to transfer the suppressed heat thus resulting to the build-up of pressure inside the condenser which could affect the distillation process. 6. Explain why some 2-methylpropene can be formed in the reaction as a byproduct. Give a mechanism for its production. How can it be removed during purification? - According to the SN1 mechanism; when alcohol is treated with a strong acid, the OH- (leaving group) is protonated first. It can be then displaced by the entering halide ion. There are cases where some of the protonated form loses the water, resulting to the formation of the free carbonium ion- this will then be stabalized by forming a double bond (alkene) with the loss of proton at the second carbon.