LOYOLA COLLEGE (AUTONOMOUS), CHENNAI – 600 034

B.Sc. DEGREE EXAMINATION – CHEMISTRY

THIRD SEMESTER – APRIL 2011

CH 3502/CH 4500 – ORGANIC FUNCTIONAL GROUPS – I

 

 

 

Date : 12-04-2011              Dept. No.                                                    Max. : 100 Marks

Time : 1:00 – 4:00

 

SECTION-A

ANSWER ALL QUESTIONS                                                                   (10×2=20)

1. What is Saytzeff’s rule? Give an example.
2. What is Sandmeyer reaction?
3. What is Clemmensen reduction?
4. What happens when acetone is treated with I₂ and NaOH?
5. Name the products obtained when anisole is treated with HI.
6. Explain why anisole cannot be prepared by the reaction of phenyl iodide and

sodium methoxide.

7. What is crossed Cannizzaro reaction?
8. How do you convert benzaldehyde  into cinnamaldehyde?
9. What is transesterification?
10. How is succinic acid prepared? Name the product obtained  when it is

heated.

 

SECTION-B

  ANSWER ANY EIGHT QUESTIONS                          (8×5=40)

11. Compare S_N1 and S_N2 reaction mechanisms.
12. Write notes on Wurtz-Fittig reaction.
13. How are alcohols prepared by hydroboration? Give  an example.
14. Why o-nitrophenol has a lower boiling  point  than p-nitrophenol?
15. How do you convert phenol into
16. a) picric acid b) salicylaldehyde

 

16. Discuss the mechanism of cleavage of ethers by HI.
17. Explain Williamson’s synthesis of ethers.
18. Discuss Norrish type-I reaction.
19. Discuss the mechanism of Wittig reaction and its uses in organic synthesis.
20. Explain Wolf-Kishner reduction with its mechanism.
21. Give any two methods of preparation of adipic acid.
22. Discuss the mechanism of acid catalysed hydrolysis of esters.

 

SECTION-C

       ANSWER ANY FOUR QUESTIONS                             (4×10=40)

 

23. Discuss the E1 mechanism for elimination reactions of alkyl halides.
24. a) Why p-nitrophenol is more acidic than phenol whereas p-cresol is less

acidic than phenol?                                                                                     (6)

1. b) What will be the product obtained when  p-cresol is treated with

CH₃COCl  and AlCl₃. Give reason.                                                          (4)

25. a) Explain why epoxides are more reactive than ethers. (4)
26. b) Name the products obtained when ethylene oxide is treated with

i)H₂O/H⁺          ii)C₂H₅OH/H⁺                iii)NH₃                                              (6)

26. Discuss the following reactions.
27. a) Benzoin condensation b) Reformatsky reaction (5+5)
28. How will you bring about the following conversions?
29. i) Salicylic acid into aspirin ii) Malonic acid into carbon suboxide

iii) Phthalic acid into phthalimide    iv) lactic acid into pyruvic acid

(v) acrylic acid into acrylamide.

28. a) Explain Norrish type-II reaction with an example.
29. b) How do maleic and fumaric acids differ in their properties?                     (5+5)

 

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