Cs/B.

PHARM/Even/Sem-4/PT-414/2018-19

MAULANA ABUL KALAM AZAD UNIVERSITY OF TECHNOLOGY,WEST BENGAL

PAPER CODE: PT- 414
PHARMACEUTICAL CHEMISTRY
(ORGANIC CHEMISTRY)

GROUP-A
(Multiple Choice Questions)
1. Choose the correct alternative for any ten of the following: 1 X 10=10

(i) The heterocycle that undergoes Diel-Alder Reaction Is

(a) Furan (b) Pyrrole

(c) Thiopene (d) Pyridazine

(ii) The reaction in which aniline is treated with glycerol to form Quinoline is known as

(a) Skraup synthesis (b) Bischler-Nepieralski synthesis

(c) Killiani-Fischer Synthesis (d) None of these

(iii) when Thiopene undergoes Friedel-craft Acylation reaction it forms

(a) 2-acetyl thiophene (b) 4-acetyl thiophene

(c) 6-acetyl thiophene (d) all of these

(iv) Optically active molecule which rotate plane polarized light in anticlock direction is

(a) Levorotatory (b) R- configuration

(c) Dextrorotatory (d) S- configurations

(v) Which confirmation has Highest Stability?

(a) Gauche (b) Fully eclipsed

(c) Staggered (d) partially eclipsed

(vi) Which of the following is strong hydride donor?

(a) 𝑁𝑎𝐵𝐻4 (b) 𝐿𝑖𝐴𝑙𝐻4

(c) 𝐵2 𝐻2 (d) None of these

(vii) Vincristine, Vinblastine is an anticancer drug, Which heterocyclic compound is present in it

(a) Purine (b) Pyrimidine

(c) Isoindole (d) Indole

(viii) Racemic mixture can be separated by –

(a) Mechanical Seperation

(b) Biochemical Method

(c) Chemical Method

(d) All of the above

(ix) Dakin reaction is useful for synthesis of

(a) Alcohol (b) Aldehyde

(c) Phenol (d) Carboxylic acid

(x) Choose The order of Electron Donating Group in Birch Reaction in Decreasing form.

(a) −𝑆 > −𝑁𝐶𝐻3 > −𝑂− > −𝑁𝐻2

(b) – 𝑁𝐶𝐻3 > −𝑂− > 𝑁𝐻2 > −𝑆

(C) – 𝑂 − > −𝑁𝐻2 > −𝑆 > −𝑁𝐶𝐻3

(d) −𝑁𝐻2 > −𝑂− > −𝑆 > −𝑁𝐶𝐻3

(xi) Compound A on dry Distillation produces furoic acid which on decarboxylation produces furan.
Identify the coumpound A
(a) Furfural

(b) Furan-2-aldehyde

(c) Mucic Acid

(d) 1,4-diketone compound

(xii) Condensation Between ammonia,aldehyde and β-ketoester is involved in

(a) Paal Knorr Synthesis

(b) Fischer’s Indole Synthesis

(c) Hantzsch Synthesis

(d) Fiest Benary Synthesis

GROUP-B
(Short Answer Type Questions)
Answer any three of the following 5x3=15
2. Discuss Skraup Synthesis Of Quinoline with Mechanism 5

3. Discuss the conformational isomerism in Cyclohexane in short 5

4. Give the Mechanism involved in Claisen-Schmidt Condensation 5

5. Explain why .

(a) Pyridine is more basic than Pyrrole and less basis than aliphatic tertiary amine.

(b) Epoxides are not considered as Heterocyclic compound 3+2

6. Nitration of Furan requires 𝐻𝑁𝑂3 and (𝐶𝐻3 𝐶𝑂)2 𝑂 where as Nitration of Furoic acid requires only
𝐻𝑁𝑂3 . Why?
 GROUP-C
(Long Answer Type Questions)
Answer any three of the following 15x3=45

7. What are heterocyclic compound? Classify different types heterocyclic compound. Discuss the
nomenclature methodologies for fused ring heterocyclic compound. Write down the Electrophillic and
Nucleophillic substitution reaction of Pyridine. In which position of Quinolone ring is electrophilic attack
most stable and why ? 2+2+3+3+3+2

8. Write Briefly about any three of the following 3x5

(a) Paal-Knor Reaction

(b) Fischer-Indole Synthesis

(c) Opennauer oxidation

(d) Bischler-Bapieralski Reaction

(e) Reduction by 𝐿𝑖𝐴𝑙𝐻4

9. (a) Write down the Gomberg reaction of Furan.

(b) Discuss Hantzsch Pyridine Synthesis.

(c) Which is more basic between Pyridine and Quinoline . why?

(d) Write any one synthesis of each:

(i) Purine (ii) Imidazole

(e) Write the Medicinal use of the following

(i) Indole (ii) Isoquinoline (iii) Furan (iv) Thiazole

3+3+2+5+2

10. Write notes on any five of the following 5x3

(a) Optical Isomers

(b) Geometrical Isomers

(c) Enantiomers

(d) Racemization
(e) Walden Inversion

(f) Chirality

(g) Regioselective Reaction

11. (a) Write down any four structure with number.

(i) Furan (ii) acridine (iii) Thiazole (iv) Benzo-[b]-thiazole (v) oxaziridine

(b) Differenciate between Clemmensen reduction and Wolff Kishner reduction.

(c) Complete the following reactions:

(i)

+ 𝑵𝒂+ 𝑵𝑯−
𝟐

(ii)

+ Ether + 𝑪𝑯𝟑 𝑪𝑯𝟐 𝑪𝑯𝟐 𝑪𝑯𝟐 𝑳𝒊

(iii)

+ 𝑪𝑪𝒍𝟐 + 𝒂𝒒 𝑲𝑶𝑯 .

(d) Write two important method for determination of configuration of geometrical isomers.

2+6+3+4