Question

Aliphatic Nucleophilic Substitution: Preparation of a Haloalkane from an alcohol

a) draw the mechanism for the reaction of t-butanol and concentrated hydrochloric acid.

b) draw a simplified reaction coordinate profile for this reaction including the structure of any intermediate/ transition states.

c) what is the rate determining step of the reaction? how would you expect the rate of the reaction of t-butyl alcohol with HCl to change if the concentration of the t-butyl chloride were doubled? what if you doubled the concentration of HCl? explain your answer in terms of the mechanism.

d) why do primary and secondary alcohol reacts via a Sn1 reaction mechanisms whereas tertiary alcohol react via a Sn2 mechanism?

e) will reaction between phenol and hydrochloric acid produce chlorobenzene? if not, explain why?

f) what products would you expect from the reaction of t-butyl chloride with each of
   (i) methanol;
   (ii) butanethiol;
   (iii) acetic acid?

g) Using relevant equations, describe a separation process and reasons for washing with sodium bicarbonate, water and saturated sodium chloride. Use a flow chart to explain.

Answer 1