I ran across a question that says:

In the following reactions, the result is sometimes one product, and sometimes a mixture of products. Design the mixture of products, explain why this is happening and predict what the main product is.

a) (1R,6S)‐1‐methyl‐7‐oxabicyclo[4.1.0]heptane + HBr; b) (2S)‐2‐methyloxirane + HCl; c) 2,2‐dimethyloxirane + HCl

Since all of them are ring opening with acid reactions, I know that the nucleophile attacks the most hindered place. What it means by mixture of products? To draw the attack on the most and least hindered place and explain that the major one is the attack on the most hindered place, or there is a racemic mixture? And if so, why is that?

  • $\begingroup$ Let's see what you think the answers are. Answers are not free ;) $\endgroup$
    – user55119
    Jun 10, 2020 at 19:29
  • $\begingroup$ @user55119 I obviously do know where and why the attack will happen each time, and how the epoxide will open. The part which i don't understand is if they want the racemic mixture or to draw the attack on the most and least hindered place and explain which is the major product. $\endgroup$ Jun 11, 2020 at 17:36
  • $\begingroup$ Structures that appear chiral are assumed to be racemic (a and b) unless indicated otherwise. The issue of mixtures would be regioisomers. You should put your attempts in the original post which will invite comments or answers. $\endgroup$
    – user55119
    Jun 11, 2020 at 17:56


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