Final - CEMA CC-X - Sem-IV - MSQ21

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Ramakrishna Mission Vivekananda Centenary College, Rahara

B. Sc.Chemistry Hons. Semester IV


Mid Semester Examination, 2021
Paper CC –X (Organic Chemistry)
Time: 1hr. Full Marks: 25
Answer any four questions taking one from each group
Group-A
1. Predict the product(s) of the following reactions and explain with mechanism. 3+3

O LiBr, HMPA, reflux


a) ?

OH

O
b)
H
?
Ph COOEt

2. Predict the product(s) of the following reactions and provide mechanism at the rearrangement
steps. 3+3

a) 1. HCN
O ?
2. LAH
3. H3O
4. NaNO2 / HCl

b) Ph Me
H H
Ph H O OH ?

Group-B
3.a) Convert: 2+2
i) Toluene into m - bromotoluene
ii) Benzene into 4 – bromo – 3 – chloroaniline
b) What would be the action of nitrous acid on each of the following: PhNMe 2, PhNHMe, 2, 5 –
Me2C6H3NH2. Give reason. 3
4. a) What happens when o – phenylenediamine and m – phenylenediamine are separately treated
with nitrous acid? Explain with mechanism. 2+2
1
b) Complete the reaction and write probable mechanism: 3
PhN2HSO4 + CuBr + HBr

Group-C
1
5. Write down the major product and explain stereochemistry using FMO theory. 2 2 × 2 = 5

O
O heat
i. + O ?

Me Me heat
ii. ?
H H

6. a) Generally, [2+2] cycloaddition is photochemically possible but not thermally. Explain using
FMO theory. 3
b) Indentify X and Y. 2
light H3C heat
X Y
CH3

Group-D
7. a) Carry out the following transformations: 2+2
(i) p-Nitrotoluene to methylquinol
(ii) m-Dinitribenzene to o-Bromobenzoic acid
b) What product would you get when benzamide is treated with P 2O5? Write the mechanism of the
reaction. 3
8. a) Comment on the product distribution of nitration of 1-methoxy-2-phenylethane with
(i) N2O5 in CH3CN; (ii) mixed acid. Explain you answer drawing appropriate structures. 5
b) How can you purify alkyl isocyanide contaminated with trace of corresponding alkyl cyanide? 2

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