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Protecting Groups, C-C Coupling, and Metathesis in Organic Chemistry, Exams of Organic Chemistry

Vignan's Foundation for Science, Technology and ResearchOrganic Chemistry

This module bank for students covers key concepts in advanced organic chemistry, including protecting group strategies, c-c coupling reactions, and metathesis reactions. It presents a series of exercises and questions designed to test students' understanding of these topics. The module includes detailed explanations of various protecting groups, their applications, and the mechanisms of different c-c coupling reactions, such as kumada, negishi, stille, suzuki-miyura, sonogashira, mizoroki-heck, and buchwald-hartwig. It also explores the principles of metathesis reactions, including ring-closing metathesis (rcm), ring-opening metathesis polymerization (romp), and acyclic diene metathesis (admet).

Typology: Exams

2023/2024

Uploaded on 10/18/2024

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Module Bank (for students) Advanced Organic Chemistry (22CT801) Module 1
VFSTR Department of Chemistry 1
Advanced Organic Chemistry (22CT801)
Instructor: Dr. Anandarup Goswami
Class: 2nd Year MSc Organic Chemistry
School of Applied Sciences and Humanities
Vignan’s Foundation for Science, Technology and Research (VFSTR)
Vadlamudi, Guntur 522 213, Andhra Pradesh, INDIA
Module Bank - Module 1 - for students
1. a) What are the criteria for selecting a good protecting group? Justify with suitable examples of
your choice. (3M)
b) Your friend Sandhya wants to synthesize the compound B from compound A. Can you help
him to design a scheme of synthesis? (3M)
c) In the syntheses of syn- and anti-1,3-Diol derivatives, DeShong and coworkers (J. Org.
Chem. 2002, 67, 6, 1754.) utilized the following reaction conditions. Can you identify the final
product? Provide suitable justification of formation of the product with detailed mechanism and
comment on its stereochemistry. (4M)
2. a) How do you define the following terms?
i. Orthogonal protection group strategy
ii. Permanent and temporary protection group
Validate with suitable examples of your choice. (3M)
b) Can you identify the products in each case and write the mechanism of formation? (3M)
c) In the syntheses of anaenamides A 24 and B 26, Brumley et al. (Org. Lett. 2020, 22, 4235.)
utilized the following reaction conditions. Can you identify the final product? Provide suitable
justification of formation of the product with detailed mechanism and comment on its
stereochemistry. (4M)
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Advanced Organic Chemistry (22CT801) Instructor: Dr. Anandarup Goswami Class: 2 nd^ Year MSc Organic Chemistry School of Applied Sciences and Humanities Vignan’s Foundation for Science, Technology and Research (VFSTR) Vadlamudi, Guntur 522 213, Andhra Pradesh, INDIA Module Bank - Module 1 - for students

  1. a) What are the criteria for selecting a good protecting group? Justify with suitable examples of your choice. ( 3M ) b) Your friend Sandhya wants to synthesize the compound B from compound A. Can you help him to design a scheme of synthesis? ( 3M ) c) In the syntheses of syn- and anti-1,3-Diol derivatives, DeShong and coworkers ( J. Org. Chem. 2002 , 67 , 6, 1754.) utilized the following reaction conditions. Can you identify the final product? Provide suitable justification of formation of the product with detailed mechanism and comment on its stereochemistry. ( 4M )
  2. a) How do you define the following terms? i. Orthogonal protection group strategy ii. Permanent and temporary protection group Validate with suitable examples of your choice. ( 3M ) b) Can you identify the products in each case and write the mechanism of formation? ( 3M ) c) In the syntheses of anaenamides A 24 and B 26, Brumley et al. ( Org. Lett. 2020 , 22 , 4235.) utilized the following reaction conditions. Can you identify the final product? Provide suitable justification of formation of the product with detailed mechanism and comment on its stereochemistry. ( 4M )
  1. a) Write the full name and the structures of the following acronyms that are routinely used in protection/deprotection chemistry. ( 3M ) Acronym Name Structure Target functional group PMB MOM THP TBDMS CBz Troc Boc Alloc Fmoc b) When your friend Tharun wanted to synthesize the product (written in the box), he used the following starting material A and reagent B. But he did not get the desired product instead he got a cyclic compound. Can you identify what product he might have got and how that is formed? Can you help her to modify the strategy so that he can synthesize the desired product. ( 3M ) c) In order to functionalize oxidized cellulose nanofibers with arginine, Wassgren et al. ( Cellulose 2022 , 29, 7603 .) utilized the following protocol. Can you identify the products after each step? Provide suitable justification of formation of the products with detailed mechanism. ( 4M )

Taxol

  1. a) According to you, why simple alkylation of amine may not lead to a better protection method? As an alternative to the challenges, you suggested, which one will you prefer – amides or carbamates? Justify your reasoning with examples. ( 3M ) b) Can you identify the products with mechanisms? How do you plan to deprotect them? ( 3M ) c) The prostaglandin precursor was prepared by Ellison and co-workers ( Tetrahedron Lett. 1975 , 8 , 499.) according to the similar scheme shown below. Can you identify the products in each step. Justify the logic behind your choice. ( 4M )
  1. a) Fill in the blanks with appropriate substrate, catalysts, co-catalysts (if any) and products. ( 3M ) Sl. No. Name of the coupling reaction Substrate Organometallic partner Catalysts Co- catalysts Products 1 Kumada 2 Negishi 3 Stille 4 Suzuki-Miyura 5 Sonogashira 6 Mizoroki-Heck 7 Buchwald-Hartwig b) If among all the C-C coupling reactions, you studied so far, if you are to choose only one reaction which is different in terms of mechanism, which one will you choose? Justify your choice with suitable mechanism. ( 3M ) c) In the attempt to synthesize (+)-Mycotrienol and (+)-Mycotrienin I, Panek and co-workers ( J. Am. Chem. Soc. 1998 , 120 , 4123.) utilized the following strategy to cyclize the ring. Can you identify the products in each step and provide the rationale for their synthesis. ( 4M )
  2. a) Identify at least one drawback of the following C-C coupling reactions and if possible, please suggest remediation methods as well. ( 3M ) a. Kumada and Negishi coupling b. Stille coupling c. Suzuki coupling d. Sonogashira coupling b) How can you synthesize the following molecule using Coupling chemistry? Comment on its mechanism of formation. ( 3M )

c) In the synthesis of ( S,S )-(+)-Dehydrohomoancepsenolide, Frustner et al. ( Org. Lett. 2000 , 2 , 2463 .) followed the steps written below. Can you identify the products and comment on the nature of reactions as well as their mechanisms. ( 4M )

  1. a) Write the full name following acronyms along with specific examples in each case. ( 3M ) Acronym Full form Example CM RCM ROMP ADMET ACM RCAM ROAMP ADIMET b) What is “Umpolung” in organic synthesis? How is it related to Grignard reagents? Comment with suitable examples. ( 3M ) c) Predict the products in each cse and comment on their mechanism of formation. ( 4M )