How to Approach Challenging Organic Chemistry II Problems?

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SUMMARY

This discussion focuses on strategies for tackling challenging Organic Chemistry II problems, specifically involving retrosynthetic analysis and the reactions of proteins with 2,4-dinitrofluorobenzene. Participants express confusion regarding the instructor's approach of presenting unfamiliar questions, emphasizing the need for hints rather than direct solutions. Key topics include the hydrolysis of protein products with HCl and the transformation of double bonds to diols. Understanding the reagents such as PCC, DMS, and O3 is also highlighted as essential for problem-solving.

PREREQUISITES
  • Understanding of retrosynthetic analysis in organic chemistry
  • Familiarity with protein chemistry and hydrolysis reactions
  • Knowledge of organic reagents like PCC, DMS, and O3
  • Basic concepts of functional groups and their transformations
NEXT STEPS
  • Study retrosynthetic analysis techniques in organic synthesis
  • Research the hydrolysis of proteins and the role of HCl
  • Learn about the conversion of alkenes to diols through various reactions
  • Investigate the mechanisms and applications of reagents such as PCC and O3
USEFUL FOR

Students enrolled in Organic Chemistry II, educators seeking to enhance problem-solving strategies, and anyone looking to deepen their understanding of organic reactions and retrosynthetic analysis.

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Homework Statement


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Homework Equations


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The Attempt at a Solution


I have no idea how to attempt this problem set. The instructor had this insane idea that if he gave us questions that we've never seen/dealt with before that he'd be doing a better job. problem is that nobody knows how to attempt these questions. I'm not trying to get anyone to do my problems for me, but can u guys give me hints on how to attempt each question? I'm really puzzled and lost.

thank you for your help
 

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1) What is the product formed when the protein is reacted with the 2,4-dinitrofluorobenzene? What would happen if that product were hydrolyzed with HCl? What would you see? There is a slight error in the problem. The individual amino acids shown after hydrolysis show the group HN- instead of the correct H2N- funtionality.

2) Approach this problem by doing a retrosynthetic analysis. What do you think the last reaction was to form this product? What were the reactants for that transformation and how were they formed?

3) Again do a retrosynthetic analysis. The product has the same number of carbons as the starting material but no double bond and two hydroxyls. What transformation(s) do you know that convert double bonds to diols? What process(es) will cause the scission of the carbon bond and produce diols?

4) Do you understand the reagents employed? (PCC, DMS, O3, CF3CO3H, etc...)
 

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