Determine the products of all stages in the following reaction

[MarcL]

Homework Statement

is treated first with Li and then with CuI.
The product reacts with chlorocyclopentane

Homework Equations

The Attempt at a Solution

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I don't know where to start exactly... it doesn't seem to be anything I've learned so far (substitution, addition ,elimination).

All I can think of is a Corey-House synthesis, don't know if I'm headed in the right direction ?

 

[Borek]

Corey-House synthesis

Sounds reasonable. What do you get when you follow that route?

 

[MarcL]

I react it with 2Li so I would get LiCl + LiCH₂CH₂CH₂CH₂CH₂CH₂ To be fair, I am sorry for the notation, I've never really been shown how to write the formula of a cyclic molecule

 

[MarcL]

And then I react it with 2CuI if I remember correctly to finally react it with another alide, correct my if I am wrong.

 

[Borek]

You can mark cyclehaxane ring with some other symbol, like RCH₂Li, or CycCH₂Li.

You seem to be on the right track, just don't stop for confirmation after every step.

Disclaimer: I am not an organiker, so there is always a chance I am wrong. But in terms of Corey-House this problem looks rather straightforward.

if I remember correctly

If you are not sure, consult your book or notes. No need to guess.