Code No. : 9391 Sub. Code : HCHM 11
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1 (8 pages) Reg. No. :... Sub. Code : HCHM 11 M.Sc. (CBCS) DEGREE EXAMINATION, APRIL First Semester Chemistry ORGANIC CHEMISTRY I (For those who joined in July 2012 onwards) Time : Three hours Maximum : 75 marks PART A (10 1 = 10 marks) Answer ALL questions. Choose the correct answer : 1. Which of the following is bicyclo [3, 2, 2] nonane?
2 2. Choose the aromatic nitrogen heterocycles. (i) only (ii) only (iii) only (i), (ii) and (iii). 3. The addition of HCl to 2-methyl-1,3-butadiene at 70º C affords 1-chloro-3-methyl-2-butene as the major product. This reaction is an example of Thermodynamic control Kinetic control Huckel s rule Markovnikov s rule. 4. A reaction run under kinetic control will involve what kind of conditions? low temperature high temperature high-speed agitation aqueous solvent. Page 2
3 5. The structure of an optically active isomer of 2-methylcyclopentanol is shown below The absolute configuration of the isomer is 1R, 2R 1S, 2S 1S, 2R 1R, 2S. 6. Among 2-heptanol, 3-heptanol, 4-heptanol, which of them can exhibit optical activity? 4-heptanol only 2-heptanol and 3-heptanol 2-heptanol and 4-heptanol all three. 7. Which reactant is used for the conversion of benzil to benzilic acid? conc. HCl conc. KOH TiCl4 KMnO4. Page 3
4 8. Which of the following happened, carbon to nitrogen migration? Wagner-Meerwein rearrangement Neber rearrangement Bayer Villiger rearrangement Benzilic acid rearrangement. 9. Which compound reacts with (CH3)2CuLi? 10. 1,3-dithiane is used to protect Diol Ketone Diamine Acetal. Page 4 [P.T.O.]
5 PART B (5 5 = 25 marks) Answer ALL questions choosing either or. Each answer should not exceed 250 words. 11. Discuss the aromaticity of fullerenes. Discuss aromatically of the following compounds. (i) (ii) (iii) 12. Describe briefly about the Cross-over experiment. Sketch energy diagram for SN2 reaction and explain with suitable example. 13. Describe the term enatiotopic and diastereotopic hydrogens with suitable examples. Page 5
6 Which of the following isomers differ in constitution and which in configuration? (i) (E)-1-bromopropene and (Z)-1- bromopropene (ii) Lactic acid and 3-hydroxybutanoic acid (iii) ( )-lactic acid and (+)-lactic acid (iv) (v) 1-chloropropene and 2-chloropropene cis-2-chlorocyclohexanol and trans-2- chlorocyclohexanol. 14. Show how the nitrene intermediate formed in Lossen s rearrangement. Discuss briefly about the migrating aptitude and memory affect. 15. Write a structure and applications of LDA in organic synthesis. What are the advantages of PTC over regular catalyst? Page 6
7 PART C (5 8 = 40 marks) Answer ALL questions choosing either or. Each answer should not exceed 600 words. 16. What is Huckel s rule of aromatically? Draw the -molecular orbital energy level diagram of cyclopentadienyl anion. Show the electronic configuration and comment on the aromaticity of the ion. Give proper mechanism for synthesis of following compounds. (i) Azulene (ii) Sydnones. 17. Give any four application of the Hammett equation. Discuss briefly about the physical significance of and. 18. Discuss briefly about the Cram s and Prelog s rule with suitable examples. Page 7
8 Explain clearly and succinctly the following stereo chemical terms. (i) Axial and planar chirality (ii) Prochirality. 19. Discuss briefly on : (i) Wagner-Meerwein rearrangement (ii) Curtius rearrangement. Give the reaction mechanism for the following reactions. (i) Tiffeneau-Demjanov reaction (ii) Arndt-Eistert synthesis. 20. Give any four synthetic uses the following reagent. (i) Vaskas catalyst (ii) LDA. Describe the synthesis and applications of the following reagents. (i) DCC (ii) Aluminium iosopropoxide. Page 8
Code No. : 5628 Sub. Code : HNAM 12
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