Organic Chem - Synthesis of alcohols

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Discussion Overview

The discussion revolves around the synthesis of alcohols with the formula C5H11OH, specifically exploring methods of formation and potential uses. Participants examine various chemical reactions that could lead to the formation of these alcohols, including hydration of alkenes, hydroboration, oxymercuration, and Grignard reactions.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant questions the applicability of hydration of alkenes for synthesizing 2,2-dimethyl 1-propanol, suggesting it may be an exception.
  • Another participant asserts that alcohols cannot be synthesized from alkenes in this context and prompts for alternative methods.
  • A participant mentions discovering hydroboration, oxymercuration, and Grignard reactions as potential synthesis methods, indicating these are not covered in their textbook.
  • Another participant suggests that reducing esters or aldehydes can produce primary alcohols and notes that Grignard reactions may not yield primary alcohols. They also mention the possibility of displacing a primary halogenated hydrocarbon to form an alcohol.

Areas of Agreement / Disagreement

Participants express differing views on the applicability of certain reactions for synthesizing alcohols, with no consensus reached on the best methods or the relevance of textbook content.

Contextual Notes

Participants highlight limitations in their textbook coverage of synthesis methods, indicating that their exploration may extend beyond the intended scope of the assignment.

purpledonkey
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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?
 
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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?
 
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!
 
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.
 

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