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Each Question Carries 5 Marks. 1. Explain Oxidations & Reductions. Section-A: Each question carries 5 marks. 1. Explain the mechanism involved in Swern Oxidation by using suitable examples. 2. Write the structures of the products of the following reactions by giving suitable mechanism. a) Cis-2-butene + OsO4 (cat), NMO, acetone-----? b) Cis-1,2-dialkyl ethane + I2/CH3COOAg(dry) + saponification -----? 3. Write about Oppenauer Oxidation with mechanism. 4. Write about BH3 Reductions & write the mechanism. 5. Give the product & mechanism of their formation for the following reaction: 6. Give the products & mechanism of their formation of the following reactions. 7. How is Manganese IV oxide prepared? Describe its use for the oxidation of alcohols to carbonyl compounds. 8. How is DIBAL prepared? Describe its uses in reductions. 9. Write short notes on Swern oxidation. 10. Write short notes on oxidation with CAN reagent. 11. Write a note on hydroboration and the regiochemistry involved in it. 12. Write the structure of the product & explain its formation. 13. Write the structure of the products in the following reaction & explain their formation. 14. Explain briefly the use of homogenous catalytic reductions with two suitable examples. 15. Which products are formed in the following reactions? How are they formed? i) Ph-CH2-CH3 + DDQ ii) Ar-NH2 + NaNO2/HCl + Bu3SnH 16. Discuss the mechanism of Birch Reduction of anisole & benzaldehyde. 17. What are the synthetic applications of tri-n-butyl tin hydride? 18. Explain the mechanism of hydrogenation with Wilkinson’s catalyst. 19. Write a note on Oppenauer oxidation. 20. Write a note on Ag2CO3 as oxidizing agent. 21. Write a note on Chromium (VI) as oxidizing agent. 22. Write about Oxidative cleavage of 1,2-diols by periodic acid. 23. Write the mechanism for the following reaction. 24. Predict the product and the mechanism for the following reaction. 25. Write the structure or chemical composition of the following reagents: a. Jones Reagent b. Collins Reagent c. PDC d. PCC e. Fetizon’s Reagent 26. Write the mechanism for the following reaction and also predict the product. 27. Write a note on DMP & IBX reagents. 28. Write the structures of the following reagents and explain one application. a. TEMPO b. TPAP 29. Write a note on the modifications of Lithium aluminium hydride. 30. Write a note on the modifications of Sodium boro hydride. 31. Write a note on Hydrogenolysis 32. Write the differences between Homogenous & Heterogenous Reduction 33. Write a note on Diimide Reduction with mechanism & example. 34. Predict the product for the following reaction with mechanism. 35. Predict the product for the following reaction with mechanism. 36. Write a note on Clemmensons reduction. 37. Write about LiAlH4 Reduction. 38. Complete the following reaction with mechanism by predicting the product. 39. Predict the products for the following reactions. 40. Write the reduction properties of BH3 by giving examples 41. Write the reduction properties of AlH3 by giving examples Section-B: each question carries 10 marks. 1. a. Explain the various steps involved in the oxidation of allylic & benzylic C-H bonds by using NBS & DDQ. b.What is Birch reduction? Give examples of the reactions. 2. a. Explain Clemmenson reduction by giving an example. b. Sketch the mechanism involved in Prevost oxidation. 3. a. Write about Swern oxidation with suitable reactions & mechanism. b. Write about NaBH4 reduction with suitable mechanism. 4. a. Write about Wolff-Kishner reduction with mechanism. b. Write about SeO2 with detailed mechanism & examples. 5.a. Predict the products in the following reactions & give the suitable mechanism. b.What happens when the following reactant is treated with LTA in C6H6 at 30oC & give the mechanism for the product formation. 6.a. Describe the use of the following reagents in organic synthesis. i. LTA ii. DMP b. Give the mechanism along with synthetic importance of the following reductions. i. Birch reduction ii. Wilkinson reduction. 7. a. Write short notes on the following: i. Swern oxidation ii. Oxidation with CAN b. Give the mechanism along with synthetic importance of the following reductions. i. Di-imide ii. DIBAL-H 8.a. Explain the conversion of ketones into esters using periodic acid. b. Mention briefly the applications of Baeyer Villiger oxidation. 9.a. Explain in detail how metals & liquid ammonia are useful in the reduction of organic substrates. b. Give mechanism of reduction of carbonyl compounds using LiAlH4 & NaBH4 10.a. Predict the products & mechanism involved in the following reactions. o i. Ph-CH=CH-CH3 + SeO2 + AcOH / 140 C----- ? ii. D (+) Glucose + HIO4 -------? b. Predict the products & mechanism involved in the following reactions. 11.a. Explain birch reduction with an example. b. Ph-CH=CH-CHO + LiAlH4-------? Write the structure of the product in the above reaction & explain its formation. 12. a. 3R2CHOH + 2H2CrO4 -------? What are the products in the above reaction? How are they formed? b. Explain diimide reduction. 13.a. Explain the heterogenous catalytic reductions with suitable examples. b. Predict the products of the following reactions & write the mechanism involved. 14.a. Compare Prevost & Woodward Oxidations. b. Explain the mechanism of benzylic oxidation with NBS. 15. a. Discuss the mechanism of Swern oxidation of a primary allylic alcohol. b. With suitable examples , explain the regioselectivity & syn addition with boron hydrides. Discuss the mechanism of hydroboration- oxidation. 16. a. Discuss the mechanism of Swern oxidation of a primary allylic alcohol. b. With suitable examples, explain the regioselectivity & syn addition with boron hydrides.Discuss the mechanism of hydroboration. 17.a. Write the mechanism of the oxidation of tetralin with DDQ. b. What are the products in the periodic oxidation of methyl-D- glucopyranoside. Give the mechanism. 18.a. Predict major & minor products formed in the following reactions. Give reasons & explain the mechanism involved. b. Write a note on the following reagents: i. IBX ii. TEMPO 19.a. Using saw-horse formulae write the products formed when cis & trans – 2 butenes are subjected to homogenous catalytic hydrogenation separately. b. Write short notes on the following reagents: i. TPAP ii. CAN 20.a. Give an account of oxidations with periodic acid. b. Write the reduction properties of DIBAL. 21.a. Discuss with suitable examples the mechanism & stereochemistry of products formed in a homogenous hydrogenation using Wilkinson’s catalyst. b. Write a note on Chromium salts as oxidizing agents. 22.a. Give an account of reduction reactions of LAH. b. Explain the reduction properties of Ketone with AlH3 23.a. Explain the reduction of acetone by boron hydride. b. Describe the stereochemistry involved in the Prevost hydroxylation. 24.a. Discuss the applications of the following reagents. Provide the mechanism. i. Dissolving metal reductions. Ii. Openauer oxidation 25. Predict the products formed in the following reactions. Give mechanism. 26. a. Discuss the use of the following reagents with mechanism. i. LTA ii. Homogenous catalytic reduction b. Predict the products formed in the following reactions. Give mechanism. 27. a. Explain the mechanism of addition of diimide to cis-2-butene. b.Write the products of following reaction with suitable mechanism. 28.a. Explain the following with suitable mechanism. b. Write notes on metal-hydride reductions. 29.a. Write a note on the synthetic utility of the following: i. LTA ii. SeO2 b. Predict the product with stereochemistry & write suitable mechanism. 30.a. Differentiate the reactivity of LAH & AlH3 in the reduction of carbonyl compounds. b. Describe the utility of periodic acid in the oxidative cleavage of diols. 31.a. Discuss the following with proper mechanism. i. Reduction of epoxides by LiAlH4 & BH3 ii. Cis-hydroxylation of olefins. b. Predict the products formed in the following reactions with mechanism. 32.a. Discuss the following with suitable mechanism. +6 i. Oxidation of alcohols by Cr ii. Reduction by Na-Liq NH3 b. Predict the products formed in the following reactions. Provide the mechanism. 33.a. Suggest suitable mechanism for the following reaction. b. Discuss the mechanism of heterogenous catalytic reduction. 34. a. Write a note on diimide reduction. b. Sketch the mechanism of homogenous catalytic hydrogenation. 35.a. Suggest the reagents with suitable mechanism in the following conversions. b. Write anote on Diimide reduction. 36. a. Differentiate the reactivity of LiAlH4 & AlH3 in the reduction of carbonyl compounds. b. Describe the utility of HIO4 in the oxidative cleavage of diols. 37.a. Write about reduction of epoxides by LAH & BH3 b. Explain cis-hydroxylation of olefins. 38.a. Explain the use of SeO2 in organic synthesis. b. Write a note on use of tri-n-butyl tin hydride. 39. a. What are the synthetic applications of DDQ & NBS. b. Illustrate the synthetic utility of the following methods with examples. i. Oppenauer oxidation ii. Prevost oxidation. 40. a. Predict the product with stereochemistry & give suitable mechanism. b. Write a note on Woodward Oxidation. 41.a.Write about MnO2 Oxidation with example of reaction with mechanism b. Write about the following reagents with mechanism & examples. i. Ag2CO3 ii. DMP reagent 42.a. Write short notes on tri-n-butyl tin hydride. b.Write about Red-Aluminium reductions. 43.a.Write about DIBAL Reductions b. Write about NaCNBH3, Selectride & Superhydride with examples. PROTECTING GROUPS SECTION A Each question carries 5 marks 1. Write the structures of benzyloxy carbonyl, t-butyloxy carbonyl, fmoc and triphenyl methyl groups. 2. How carboxylic acid groups of peptides are protected and activated? 3. How alcohols are protected by ethers and silyl ethers. Explain with examples? 4. How alcohols are protected by TBDMS and THP. Explain with two examples? 5. How carbonyls are protected by acetal and ketal formation? Explain with examples? 6. Write a short notes on coupling with DCC 7. How the carboxylic acid groups are protected by ester formation? Explain with 2 applications 8.
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