Question

Are there any good resources for a large amount of SN1 v. E1 v. SN2 v. E2? My professor likes to ask these types of problems on exams and niether book I am using Smith 3rd or Wade 8th has this problem type. I have exhausted the entire first and second page of Google in search of problems and still don't feel quite confident.

Answer 1

I would like to tell you an important trick to solve questions related to substitution and elimination reactions.

Step 1

Check for SN1 or E1

generally, SN1 and E1 reactions are preferred by tertiary and sometimes secondary carbon atoms.

step 2

then see the acid and base used, check whether it is strong or weak.

suppose if 0.001M or mild concentration of NaOH is used in H2O then, in this case, SN₁ will be preferred over E1 but is 0.1 M or highly concentrated NaOH is used in less water, then elimination is favored.

Step 3.

After checking for SN1 and E1,

Now check for SN2 or E2 which are generally preferred by less substituted carbon atoms 1^o or secondary carbon atoms.

After that check for the base,

if the base is substituted then, Elimination is favored otherwise SN2 (generally EtOH/NaOEt favors SN2)

And NaOC(CH3)3/ HOC(CH3)3 favours E2