How to synthesize 4‐[(4,4‐dimethylpentyl)oxy]‐2,2,8,8‐tetramethylnonane starting with 4,4‐dimethylpent‐1‐ene?
Divide your alkene starting material in two portions - one twice the amount of the other.
Take the larger portion and do an anti-Markovnikov addition of HBr to it using peroxide or light reference to give the terminal bromide (1-Bromo-4,4-dimethylpentane).
Take the smaller portion and ozonolyse it, working up with Dimethyl Sulfide to give the aldehyde (3,3-dimethyl butanal).
Take half the bromide material and form the Grignard with Mg metal. Add the Grignard to the aldehyde. Work up and isolate the resulting secondary alcohol. Dissolve the secondary alcohol in DMF at 0c and form the alkoxide with NaH, add the second portion of the bromide to the alkoxide solution. Work up, isolate and purify to obtain the desired product.