# Parameters by which to distinguish SN1 from E1

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?

• Why eliminate the E2 mechanism in basic medium? – user55119 Aug 6 at 20:14
• @user55119 The way I understood the material, weak nucleophiles and E2 do not go together well. Am I wrong? – Pregunto Aug 7 at 8:53
• [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 – user55119 Aug 7 at 14:19
• @user55119 I should not be called "Ammonium hydroxide" and is not enough to remove weakly basic hydrogens. – Mithoron Aug 8 at 0:25