Neuman stability and chiral question

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Discussion Overview

The discussion revolves around two questions related to organic chemistry: one concerning the stability of certain molecular structures and the other regarding chirality. Participants are examining their reasoning and the answers provided in an ACS organic review book, seeking clarification on their thought processes and the underlying concepts.

Discussion Character

  • Homework-related
  • Debate/contested
  • Conceptual clarification

Main Points Raised

  • One participant expresses confusion over the stability question, believing that the strain from two OH groups should be greater than that from an OH group with a CH3 group, and seeks clarification on their reasoning.
  • Another participant questions the chirality of the given structures, noting that they guessed D due to the sp3 hybridization of nitrogen in one structure, while also arguing that the CH3 group in another structure does not create chirality due to identical hydrogen atoms.
  • A later reply suggests considering the exchange of a methyl group and a proton to determine superimposability, which leads to a discussion about optical activity and chirality centers.
  • One participant corrects their earlier statement about the stability question, indicating that the answer is actually D, not C, and expresses uncertainty about why the answer is not A instead.

Areas of Agreement / Disagreement

Participants do not appear to reach a consensus on the correct answers to the stability and chirality questions. There are multiple competing views and ongoing confusion regarding the reasoning behind the answers.

Contextual Notes

Participants express uncertainty about the definitions of chirality and stability, and there are indications of missing assumptions in their reasoning processes. The discussion reflects a reliance on the specific context of the ACS organic review book without resolving the underlying concepts.

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Homework Statement



I have two questions. I have attached two pictures, 1 for each.

1. For the question about stability, the answer is C, but I thought it should be B. I would imagine the strain of two OH groups would be greater than an OH group with a CH3 group. Can someone explain what is wrong in my thinking?

2. For the question about chirality, the answer is C. I don't see how any of them can be chiral, but I guessed D because the N in II is at least sp3 because of a lone pair of electrons. I don't see any sp3 carbons in III except in the CH3 group, but that is not chiral because the three H's are the same.

These questions are from my ACS organic review book.

Thank you for your help!

Homework Equations





The Attempt at a Solution

 

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Puchinita5 said:

Homework Statement



I have two questions. I have attached two pictures, 1 for each.

1. For the question about stability, the answer is C, but I thought it should be B. I would imagine the strain of two OH groups would be greater than an OH group with a CH3 group. Can someone explain what is wrong in my thinking?

2. For the question about chirality, the answer is C. I don't see how any of them can be chiral, but I guessed D because the N in II is at least sp3 because of a lone pair of electrons. I don't see any sp3 carbons in III except in the CH3 group, but that is not chiral because the three H's are the same.

These questions are from my ACS organic review book.

Thank you for your help!

Homework Equations





The Attempt at a Solution


For 2, what happens if you exchange the methyl group and the proton attached to the same carbon. Can you superimpose this on your original?
 
I'm sorry I'm not sure what you mean ? :-/
 
OK, how do you know that cis and trans but-2-ene are different compounds?
 
Because they have different physical properties? lol I feel I am missing something.
 
Hmmm okay so I see now what you mean by exchanging the methyl and proton. And you wouldn't be able to superimpose these. Is that what makes them optically active? So it doesn't matter that there are no "chirality centers? "
 
Oops I just realized, i mistyped. The answer to the stability question is D, not C. And I think the answer should be A. Why is the answer not A? (When I originally posted I had said I thought the answer should be B but this was because I ordered my choices backwards. I really meant A) But I still don't understand why for the same reason. But just in case anyone was really confused. :)
 

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