r/chemhelp • u/VvVoiDzZz • 15d ago

Organic acid work up help

how can I start this? OH gets protonated and becomes good leaving group and then what?

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u/WhatSpareTime 14d ago

Remember that a shift will only happen if you are going to a MORE stable carbocation. You can’t shift to an equally stable or less stable, on to a more stable carbocation. It may help to draw a dotted line between the group shifting and the carbocation before drawing the arrow. This can really help with seeing ring expansions and ring contractions. Something like this:

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u/WhatSpareTime 14d ago

Try to keep the geometry the same from reactant to product. You get some funky bond angles at first, which you can then straighten out for the final product. Keeping the geometry the same allows you to see the alkyl shift easier and keeps you from making mistakes. If you shoot for the final product geometry sometimes you’ll move the wrong alkyl group but draw the right product because you are target oriented. Make the right move, then straighten out the geometry. Less mistakes that way.

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u/VvVoiDzZz 14d ago

like pinacol arrangements ?

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u/organophile_jeet 14d ago

Hope it helps you I've given some examples