Report: Nucleophilic Substitutiorn Results 1. Report the volume of tert-butyl ch
ID: 711564 • Letter: R
Question
Report: Nucleophilic Substitutiorn Results 1. Report the volume of tert-butyl chloride that was collected 2. Report the boiling point of tert-butyl chloride 3. Look up the boiling point of tert-butyl alcohol (online or use the chemistry/physics handbook) 4. If instructed, attach the IR spectrum and label the relevant peak s. Conclusions and questions 1. Based upon the boiling points of tert-butyl chloride and tert-butyl alcohol, do you predict that distillation is an effective was to separate tert-butyl chloride from any un- reacted tert-butyl alcohol:? 2. Calculate the percent yield of your tert-butyl chloride product. (Go back to the procedure to figure out how much starting material you used and the limiting reactant) 3. Review hydride shifts (in your textbook). Propose a mechanism for each of the following reactions HCI 25 CI OH HCl OH 25 CI 4. Answer the following questions for the mechanisms above a. Comment on the relative stability of the carbocation intermediate. b. Identify the acid that you used in the first step c. Identify the nucleophile and electrophile in the last step. d. Is the first reaction SN, or SN2, why?Explanation / Answer
4.
a.
the taken alcohol is tertiery butyl alcohol
so the carbo cation formed here is tertiery butyl carbo cation which is more stable
b.
the acid that was used is hydrochloric acid
c.
the nucleophile in the last step is Cl- (chloride ion)
the electrophile in the last step is H+ (proton)
d.
both are SN1
in first it will form directly carbo cation
in last step first primary will form that will rearrange in to tertiery