TBR Orgo Book 1 Orgo Question

[inycepoo]

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Hey all,

Section 3 Equilibrium, Passage I on 52-Q exam, #4, pp. 228. Picture attached for those without the book.

How come carbon b isn't said to be able to carry a positive charge? Hydrogenation of the double bond between carbons c and b easily gives a stable tertiary carbocation. The question stem says "could," so I don't think the relative possibility of it occurring is taken into account, right?

 

[Synapsis]

Hey all,

Section 3 Equilibrium, Passage I on 52-Q exam, #4, pp. 228. Picture attached for those without the book.

How come carbon b isn't said to be able to carry a positive charge? Hydrogenation of the double bond between carbons c and b easily gives a stable tertiary carbocation. The question stem says "could," so I don't think the relative possibility of it occurring is taken into account, right?

View attachment 24085

Not exactly sure what the question is (I don't have that test), but if you draw the second resonance form for carbon b, you can see that it's an enolate. But that carbon has essentially the same amount of electron density around it as before - it's still on one end of the double bond. No resonance forms indicate it having a positive, or partial positive charge.