Cochin University of Science and Techology (CUST) 2007-3rd Sem M.Sc Chemistry IN APPLIED CHE 2303 ORGANIC - Question Paper
AC.3/07.3 M.Sc. DEGREE III SEMESTER EXAMINATION IN APPLIED CHEMISTRY, NOVEMBER 2007
CC&CHE 2303 ORGANIC CHEMISTRY III
Time: 3 Hours
Maximum marks : 50
(Answer ALL questions)
(All questions carry EQUAL marks)
Formulate the following:
(1)
(2)
(3)
Benzoic acid Birch Reduction _ij.
('*) Anisole Birch Reduction
->
What is Swern oxidation ?
Predict the product(s) in the following:
(4)
How would you bring about the following transformation ?
, v UCOCs_
(5)
j }4 (J box}
-->
<?-; X.
x
i \
S-
Complete the following reactions:
c ui-codu
Uxsd / tor I
hJ
I
Hi}
Outline the mechanism for the formation of flavone from benzoyloxy acetophenone by Baker-Venkataraman method.
(6)
(7)
How would you account for the formation of a mixture of 21- and 31-phosphates from RNAs
by alkaline hydrolysis.
(8) What is replication of DNAs ?
(9) How would you effect the following transformation ? Cholesterol >5/3 - cholestan - 3/? - 01 .
(10) Outline the sysnthesis of alanine by Streckers method.
PART -B
(All questions carry EQUAL marks)
Formulate the product(s) in the following reactions. Show the stereochemistry wherever applicable:
?
?
(5x1=5)
OR
Explain and compare the following:
(i) Woodward and Prevost hydroxylations
(2'A x 2 =5)
(ii) Hydrazine and Diimide Reduction
(i) Why a - organochromium (111) reagents are better reagents than Grignard reagents ? Explain.
(iii) 9-BBN (9-Borabicyclononane) is a regiospecific reagent when
compared to Borane-Account for this. (2A+2lA=5)
OR
Discuss the following:
(i) Gilman reagent
(ii) Phase transfer catalyst (2'A+2'A=5)
Explain the following:
(i) Synthesis of penicillin
(ii) Nomenclature of three membered ring heterolycles containing one heteroatom. 2'A+2'A~5)
OR
Establish the structure of Cephalosporin.
(Contd.....3)
Compare the electrophilic substitution reactions of Quinoline and isoquinoline with suitable illustration.
OR
V. A B.
VI. A, B.
VII. A. B.
VIII. A. B.
IX. A. B.
How would you differentiate simple 4-phenyl-coumarin from flavone by chemical and physical methods ?
Define Biogenesis and Biosynthesis. Explain the biosynthesis of Shikimic acid.
OR
Outline the synthesis of the following:
(i) Vitamin C (ii) Deoxy sugars
What is isoprene rule ? Write a note on biosynthesis of terpenoids.
OR
Give a brief account on classification and structure of prostaglandins.
How would you confirm the presence and position of two double bonds, carboxylic group, isopropyl group and angular-methyl group in Abietic acid ? Also explain how UV absorption spectrum of abietic acid is helpful in deciding the two double bonds in conjugation.
. OR
Elucidate the structure of atropine.
What is the importance of the discussion on conformational isomers to our consideration of secondary, tertiary and quaternary structures of proteins ?
OR
Discuss the following:
(i) Enantioselective synthesis of amino acids.
(ii) Function of chymotrypsin.
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