Questions Chiral centers,Markonikov's rule

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Discussion Overview

The discussion revolves around questions related to chiral centers and Markonikov's rule, focusing on the identification of chiral centers in various chemical compounds and the correct application of addition reactions in organic chemistry. The scope includes homework-related queries and technical explanations regarding stereochemistry and reaction mechanisms.

Discussion Character

  • Homework-related
  • Technical explanation
  • Debate/contested

Main Points Raised

  • One participant notes that H2S is a product in a reaction, not a reactant.
  • Another participant points out that a chiral center is missing in the elimination products, specifically at the 4-position Carbon, which is not symmetrical.
  • There are claims that the bonus question is incorrect due to the presence of two chiral centers in the compounds discussed, with the amine not being a chiral center.
  • It is mentioned that 3- and 4-vinylcyclohexanethiol each have two chiral centers.
  • One participant argues that the addition of Br2 to double bonds occurs anti, not randomly, suggesting the use of models for better understanding.
  • Participants express frustration over mistakes made in their answers, indicating a struggle with the material.

Areas of Agreement / Disagreement

Participants express disagreement regarding the number of chiral centers in certain compounds, with some asserting there are two chiral centers while others believe there is only one. The discussion remains unresolved as participants correct each other without reaching a consensus.

Contextual Notes

There are limitations regarding the assumptions made about the reactivity of the amine and the conditions under which the addition reactions occur. The discussion also reflects uncertainty in the identification of chiral centers and the application of stereochemical principles.

predentalgirl1
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I put all of my questions/solutions in the attached file...could someone please check over them before 7:00 am to see if I have them correct? Thanks in advance!
 

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Last edited:
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Question 1:
part c) H2S is a product, not a reactant.
part d) You're missing a chiral center. The 4-position Carbon is chiral for the elimination products. It's not quite symmetrical.

bonus looks correct!
 
Bonus is wrong. There are 2 chiral centers and neither is near enough to the amine to cause racemization. The amine is not a chiral center.

3- and 4-vinylcyclohexanethiol each have 2 chiral centers.

e) is wrong since Br2 adds anti to double bonds, not randomly. You need to make models to see it maybe.
 
Last edited:
chemisttree said:
Bonus is wrong. There are 2 chiral centers and neither is near enough to the amine to cause racemization. The amine is not a chiral center.

I hate it when I rush through these questions! I'm wrong, of course. You were correct in your answer that there is only one chiral center. That said, the amine is certainly not a chiral center and is not reactive with the chiral alcohol.

3- and 4-vinylcyclohexanethiol each have 2 chiral centers.

Arrrrgggghhhh! I did it again here! There are 2 chiral centers on the 3-vinyl compounds and only 1 for the 4-vinyl compounds.

e) is wrong since Br2 adds anti to double bonds, not randomly. You need to make models to see it maybe.

Got that one right.
 

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