Determine the products of all stages in the following reaction

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Discussion Overview

The discussion revolves around a multi-step organic reaction involving the treatment of a compound with lithium and copper iodide, followed by a reaction with chlorocyclopentane. Participants explore the synthetic pathway and the expected products at each stage, focusing on the Corey-House synthesis method.

Discussion Character

  • Homework-related
  • Exploratory
  • Technical explanation

Main Points Raised

  • One participant expresses uncertainty about how to start the problem, noting it does not align with their previous learning on substitution, addition, or elimination reactions.
  • Another participant suggests that the Corey-House synthesis is a reasonable approach and asks for the expected products from that route.
  • A participant proposes that reacting with lithium would yield LiCl and a lithium alkyl compound, although they express uncertainty about the notation for cyclic molecules.
  • There is a suggestion that after the lithium reaction, the next step involves reacting with copper iodide, though the details are not fully confirmed.
  • A later reply encourages the participant to use alternative notation for cyclic structures and reassures them that they are on the right track, while also advising caution and suggesting consulting resources for confirmation.
  • One participant acknowledges their lack of expertise in organic chemistry, indicating that there is a possibility of error in their contributions.

Areas of Agreement / Disagreement

Participants generally agree on the use of the Corey-House synthesis as a potential pathway, but there is no consensus on the specific products or the notation for cyclic molecules. Uncertainty remains regarding the details of the reactions and the expected outcomes.

Contextual Notes

Participants express limitations in their understanding of notation for cyclic compounds and the specifics of the reactions involved. There is also a mention of potential errors in reasoning due to varying levels of expertise among participants.

Who May Find This Useful

Students studying organic chemistry, particularly those interested in synthetic methods and reaction mechanisms, may find this discussion relevant.

MarcL
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Homework Statement


upload_2014-12-16_12-16-33.png

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 ?
 
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MarcL said:
Corey-House synthesis

Sounds reasonable. What do you get when you follow that route?
 
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
 
And then I react it with 2CuI if I remember correctly to finally react it with another alide, correct my if I am wrong.
 
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.

MarcL said:
if I remember correctly

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

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