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UKChO 2020 Q6 help

Can someone please explain question 6 part D on the UKChO 2020 paper? I am especially confused with how anion E is formed. Thanks for any response in advance.

(edited 3 months ago)

Reply 1

TSR Jessica

Sorry you've not had any responses about this. :frown:

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Here's a link to our subject forum which should help get you more responses if you post there. :redface:

Reply 2

ahmed995482

Original post by playfulsheep

Can someone please explain question 6 part D on the UKChO 2020 paper? I am especially confused with how anion E is formed. Thanks for any response in advance.

the t-BuO⁻ anion is very unstable due to all of the alkyl groups on the same carbon pushing electron density onto the oxygen (positive inductive effect). Generally, when a negative charge can be delocalised (spread out over several atoms) the structure becomes more stable and if the charge is localised (here, on the O) it’s unstable. Because it’s unstable, it binds to nearly any proton it can find to stabilise the negative charge, even if it’s from a non polar C-H bond - hence it’s a base as stated. Looking at the way the synthesis is going, the only logical place to take the proton is the bottom carbon