Organic Chem - Synthesis of alcohols

[purpledonkey]

After drawing the 8 alcohols with the formula C5H11OH, I'm asked to "Describe how they are formed and give two uses for this type of alcohol."

The only example in my text for this is the hydration of an alkene which, at a glance, wouldn't make sense for 2,2-dimethyl 1 propanol. Is this one just the exception or am I just digging too deep intop a topic that is rather lightly covered?

 

[chemisttree]

You obviously can't make an alcohol from an alkene in this system. What other chemistry do you know that could lead to an alcohol?

 

[purpledonkey]

Well my continued searching brought me to the terms hydroboration, oxymercuration and grignand reaction, so considering none of these terms are present in my text, I'd say I'm taking this question further than intended. Thanks though!

 

[chemisttree]

You can reduce an ester or aldehyde to produce a primary alcohol. I don't think that the grignard route will result in a primary alcohol. You can also displace a primary halogenated hydrocarbon to make an alcohol.