AAMC Practice Test #1 Chem/Phys Section Question

[agurl1000]

So I just took the AAMC test and was not sure why choice A was true. It talks about a tertiary alcohol, but in the passage, I only see a secondary alcohol. Could someone explain this to me? I might be missing something really obvious but I can't see it. I have the question and the passage attached! Could someone also explain all the other answer choices too?

Thanks in advance!

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[freak7]

So I just took the AAMC test and was not sure why choice A was true.
Thanks in advance!

"does NOT"

 

[agurl1000]

"does NOT"

I understand that it says does NOT, so that has to mean it occurs. So my question is why do tertiary alcohols work? I could be missing something and making a stupid mistake but I cannot see it!

 

[freak7]

I understand that it says does NOT, so that has to mean it occurs. So my question is why do tertiary alcohols work? I could be missing something and making a stupid mistake but I cannot see it!

I think you're confusing yourself. The answer is correct because the reaction does not occur most readily with tertiary alcohols

Edit: sorry I misread

 

[NextStepTutor_3]

Hi there! You are correct that malic acid, shown in the passage, is not a tertiary alcohol. However, choice A says only that "the reaction occurs most readily with tertiary alcohols" - not that there actually was a tertiary alcohol shown in the passage. The reaction mechanism is E1, which occurs via a carbocation intermediate (eliminate C). Such reactions occur most rapidly with tertiary substrates, since tertiary carbocations are more stable than less substituted carbocations and are thus more likely to form (eliminate A).

We're left with choice D, and we see that both fumaric and maleic acid are formed, rather than just a single isomer. This supports D being the answer to this NOT question.

Good luck with your prep!