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i) Starting from any alkene
You can create this from 2-butene, or an alkene with a double bond on carbon-2. It theoretically doesn’t matter whether it’s cis or trans.
I would do this:
ii) Starting from a grignard reagent
I don’t really see the point of starting from a Grignard reagent since it’s usually a nucleophile… but:
iii) Start from step 2 of part i) and do the same thing from that point on
iv) Starting from any sodium alkanoate
This’ll take a while to do in real life…
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