I am new to organic chemistry and am struggling with the following very basic question:

Given is the following reaction:

$$\ce{(CH3)3CCl + NH3(aq) →}$$

I am supposed to analyse the end-product (the temperature is not given). However, how do I determine whether this is $\mathrm{S_N1}$ or $\mathrm{E1}?$ I understand $\ce{NH3}$ is a weak nucleophile and that the carbon atom is tertiary, which together eliminate $\mathrm{S_N2}$ and $\mathrm{E2},$ but I was not given any other parameters with which to carry out the evaluation.

Obviously, the end-product will depend on whether the reaction is $\mathrm{S_N1}$ or $\mathrm{E1},$ so how do I establish which one of the two it will be?

  • $\begingroup$ Why eliminate the E2 mechanism in basic medium? $\endgroup$ – user55119 Aug 6 '19 at 20:14
  • 1
    $\begingroup$ @user55119 The way I understood the material, weak nucleophiles and E2 do not go together well. Am I wrong? $\endgroup$ – Pregunto Aug 7 '19 at 8:53
  • $\begingroup$ [tert-Butylamine is not prepared from the chloride][1]. Ammonium hydroxide is basic and will lead to isobutylene via E2 elimination. In a neutral medium such as water there will be an equilibrium mixture of alcohol (SN1) and alkene (E1). [1]: en.wikipedia.org/wiki/Tert-Butylamine $\endgroup$ – user55119 Aug 7 '19 at 14:19
  • $\begingroup$ @user55119 I should not be called "Ammonium hydroxide" and is not enough to remove weakly basic hydrogens. $\endgroup$ – Mithoron Aug 8 '19 at 0:25

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