Organic Chemistry: Alkyne Synthesis and Addition Homework Solution

[romantichero7]

Homework Statement

http://i.imgur.com/1tKcV5w.jpg?1

First we start with ____ and immediately add ____ followed by ____ work up to give the new functional group____ . Then treatment with ____ and ____ will give____ (syn / anti) addition to give the ____ (stereochemistry)____ (functional group) . The final product can be formed by adding____ .

Homework Equations

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The Attempt at a Solution

I need to fill in the aragraph. My issue is mostly about how to add carbons in such a way that I can get the OH on that one carbon.. I thought about turning the alkyne into an alkynyl anion and then adding a ketone but that doesn't get the O in the right place. Any advice?

 

[Asim Riaz]

We start with propyne and immediately add sodium amide followed by hydrogenation work up to give the new functional group aldehyde. Then treatment with bromine and methanol will give anti addition to give the (E) stereochemistry (aldehyde). The final product can be formed by adding hydroboration-oxidation.