How can we convert 1-hexene to cis-3-octene using alkynes as intermediates?

[whatlifeforme]

Organic: Alkene to Alkyne

I am trying to do a synthesis of 2-Octyne from 1-heptene. Conversion of the triple bond to a double bond is pretty easy, but i also have to add an alkyl group, and the double bond must remain on the original triple bond location.

Thus, so far thoughts:
1. remove hydrogens from double bond

2. add ch3 to terminal carbon to replace hydrogen.
CH3-BR ?

Question 2: Propose a synthesis of cis-3-octene starting from 1-hexene.

 

[chemisttree]

You need to review the http://courses.chem.indiana.edu/c341/documents/C341S2010CH7Alkynes.pdf"