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
ANSWER ALL QUESTIONS (10×2=20)
- What is Saytzeff’s rule? Give an example.
- What is Sandmeyer reaction?
- What is Clemmensen reduction?
- What happens when acetone is treated with I2 and NaOH?
- Name the products obtained when anisole is treated with HI.
- Explain why anisole cannot be prepared by the reaction of phenyl iodide and
- What is crossed Cannizzaro reaction?
- How do you convert benzaldehyde into cinnamaldehyde?
- What is transesterification?
- How is succinic acid prepared? Name the product obtained when it is
ANSWER ANY EIGHT QUESTIONS (8×5=40)
- Compare SN1 and SN2 reaction mechanisms.
- Write notes on Wurtz-Fittig reaction.
- How are alcohols prepared by hydroboration? Give an example.
- Why o-nitrophenol has a lower boiling point than p-nitrophenol?
- How do you convert phenol into
- a) picric acid b) salicylaldehyde
- Discuss the mechanism of cleavage of ethers by HI.
- Explain Williamson’s synthesis of ethers.
- Discuss Norrish type-I reaction.
- Discuss the mechanism of Wittig reaction and its uses in organic synthesis.
- Explain Wolf-Kishner reduction with its mechanism.
- Give any two methods of preparation of adipic acid.
- Discuss the mechanism of acid catalysed hydrolysis of esters.
ANSWER ANY FOUR QUESTIONS (4×10=40)
- Discuss the E1 mechanism for elimination reactions of alkyl halides.
- a) Why p-nitrophenol is more acidic than phenol whereas p-cresol is less
acidic than phenol? (6)
- b) What will be the product obtained when p-cresol is treated with
CH3COCl and AlCl3. Give reason. (4)
- a) Explain why epoxides are more reactive than ethers. (4)
- b) Name the products obtained when ethylene oxide is treated with
i)H2O/H+ ii)C2H5OH/H+ iii)NH3 (6)
- Discuss the following reactions.
- a) Benzoin condensation b) Reformatsky reaction (5+5)
- How will you bring about the following conversions?
- 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.
- a) Explain Norrish type-II reaction with an example.
- b) How do maleic and fumaric acids differ in their properties? (5+5)
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