GUJARAT TECHNOLOGICAL UNIVERSITY

Bachelor of Pharmacy
Subject Code: BP401TT
SEMESTER: IV
Subject Name: Pharmaceutical Organic Chemistry III

Scope: This subject imparts knowledge on stereo-chemical aspects of organic compounds and organic
reactions, important named reactions, chemistry of important hetero cyclic compounds. It also
emphasizes on medicinal and other uses of organic compounds.

Objectives: Upon completion of the course the student shall be able to

1. understand the methods of preparation and properties of organic compounds
2. explain the stereo chemical aspects of organic compounds and stereo chemical reactions
3. know the medicinal uses and other applications of organic compounds

Teaching scheme and examination scheme:

Teaching Scheme Evaluation Scheme

Theory Tutorial Practical Total Theory Practical
External Internal External Internal
3 1 0 4 80 20 0 0

Sr No Topics %
weightage
1. Stereo isomerism 10
Optical isomerism –
Optical activity, enantiomerism, diastereoisomerism, meso compounds
Elements of symmetry, chiral and achiral molecules
DL system of nomenclature of optical isomers, sequence rules, RS system of
nomenclature of optical isomers
Reactions of chiral molecules
Racemic modification and resolution of racemic mixture.
Asymmetric synthesis: partial and absolute
2. Geometrical isomerism 10
Nomenclature of geometrical isomers (Cis Trans, EZ, Syn Anti systems)
Methods of determination of configuration of geometrical isomers.
Conformational isomerism in Ethane, n-Butane and Cyclohexane.
Stereo isomerism in biphenyl compounds (Atropisomerism) and conditions for
optical activity.
Stereospecific and stereoselective reactions
3. Heterocyclic compounds: 10
Nomenclature and classification
Synthesis, reactions and medicinal uses of following compounds/derivatives
Pyrrole, Furan, and Thiophene
Relative aromaticity and reactivity of Pyrrole, Furan and Thiophene
Synthesis, reactions and medicinal uses of following compounds/derivatives 8
4. Pyrazole, Imidazole, Oxazole and Thiazole.
Pyridine, Quinoline, Isoquinoline, Acridine and Indole. Basicity of pyridine
Synthesis and medicinal uses of Pyrimidine, Purine, azepines and their
derivatives
5. Reactions of synthetic importance 7
Metal hydride reduction (NaBH4 and LiAlH4), Clemmensen reduction, Birch
reduction, Wolff Kishner reduction.
Oppenauer-oxidation and Dakin reaction.
Beckmanns rearrangement and Schmidt rearrangement.

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 GUJARAT TECHNOLOGICAL UNIVERSITY
Bachelor of Pharmacy
Subject Code: BP401TT
Claisen-Schmidt condensation

Recommended Books (Latest Editions)

1. Organic chemistry by I.L. Finar, Volume-I & II.

2. A text book of organic chemistry – Arun Bahl, B.S. Bahl
3. Heterocyclic Chemistry by Raj K. Bansal
4. Organic Chemistry byMorrison and Boyd
5. Heterocyclic Chemistry by T.L. Gilchrist

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Seat No.: _____ Enrolment No. _____________

GUJARAT TECHNOLOGICAL UNIVERSITY

B. PHARM. SEMESTER– IV • EXAMINATION – WINTER -2023

Subject Code: BP401TT Date: 23/01/2024

Subject Name: PHARMACEUTICAL ORGANIC CHEMISTRY III
Time: 2:30 PM TO 5:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.
Q.1 (a) Give the Preparation, Properties and Chemical reaction of Pyrrole. 06
(b) Discuss the Sequence rule to assign configuration with example. 05
(c) Comment on the following 05
1. Pyridine is more basic than Pyrrole.
2. Pyridine is less basic than aliphatic amines
Q.2 (a) Write the Structure, Reaction, and Medicinal use of Imidazole, Oxazole. 06
(b) State and explain Recemic mixure and write note on different methods of 05
resolution.
(c) Give brief note on reaction involve in LiAlH4 and NaBH4 05
Q.3 (a) Define following terms. 06
1) Enantiomers 2) Atropisomers 3) Conformational isomer 4) Diastereoisomer
5) Heterocyclic compound 6) Chirality
(b) Describe Conformational isomerism of Cyclohexane 05
(c) Explain Clemmensen reduction in detail 05
Q.4 (a) Give Brief note with mechanism on 06
a) Dakin Reaction b) Schmidt rearrangement
(b) Explain Hantzsch Synthesis in detail with structural 05
(c) Discuss basicity of pyridine 05
Q.5 (a) Explain any two synthesis and medicinal uses of Pyridine 06
(b) What are Stereospecific and Stereoselective reactions? Explain in detail 05
(c) Write in detail about Stereochemistry of Biphenyl compounds 05
Q. 6 (a) Draw the structures of azepines and acridine and discuss any two reactions of 06
them.
(b) Comment on following statements 05
i) Furan has high boiling point than Pyrrole.
ii) Furan is aromatic in nature although it containing two lone pair electron.
iii) Thiophene is more aromatic than pyrrole.
iv) Electrophilic substitution on pyridine favour at C3 position.
v) Pyrrole is more basic than aliphatic amine

(c) Discuss nomenclature and classification of thiophene and furan 05

Q.7 (a) Give the structure of: 06
(1) Indole (2) Pyridine (3) Isoquinoline (4) Imidazole
(5)Acridine (6) Thiophene
(b) Define plane polarized light and discuss optical activity in detail 05
(c) Draw the structures of quinoline and isoquinoline and discuss any one synthesis 05
of both.

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.Ph. -SEMESTER– IV • EXAMINATION –WINTER -2022

Subject Code: BP401TT Date: 22/12/2022

Subject Name: Pharmaceutical Organic Chemistry-III
Time: 02:30pm to 05:30pm Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) What do you mean by Racemic modification? Write down different methods of 06
resolution of racemic mixture.
(b) Explain how Pyrrole is both acidic as well as basic. 05
(c) Give the biological and medicinal significance of Furan derivatives. 05
Q.2 (a) Give two methods of synthesis of these followings: 06
i) Imidazole ii) Thiophene iii) Furan.
(b) Write down the various reactions of chiral molecules. 05
(c) Write the chemical preparation and reactions of Pyridine. 05
Q.3 (a) Write a short note on Birch Reduction with its mechanism. 06
(b) Enlist the different methods to determine the configuration of geometrical 05
isomers.
(c) Write a short note on Relative Configuration. Give an example of it. 05
Q.4 (a) Discuss the following: 06
i. Fischer Indole synthesis
ii. Paal-Knorr synthesis of Pyrrole.
(b) Give detail stereoisomerism of compounds which do not have chiral center. 05
(c) What do you mean by conformation? Write in detail conformation of butane. 05
Q.5 (a) Draw the structure of the followings: 06
1H- Azepine
Acridine
3-imidazoline
1,3- diazine
1,2- oxazole
Pyrrolo [2,3-b] indole.
(b) Write a short note on Conformation of cyclohexane. 05
(c) Describe the various methods to draw an enantiomers with suitable example. 05
Q. 6 (a) Write short note on these followings: 06
i. Chichibabin reaction
ii. Skraup synthesis
(b) Write down the various rules of CIP system. Give suitable example of it. 05
(c) What do you mean by optical activity? Describe the conditions for optical 05
activity.
Q.7 (a) Write a short note on stereoselective and stereospecific reaction along with 06
example.
(b) Write the chemical Preparation and reactions of Pyrazole. 05
(c) Describe in detail metal hydride reduction with suitable examples. 05

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GUJARAT TECHNOLOGICAL UNIVERSITY

B. Ph. SEM -IV • EXAMINATION – SUMMER - 2022

Subject Code: BP401TT Date: 14/07/2022

Subject Name: Pharmaceutical Organic Chemistry-III
Time: 10:30AM TO 1:30PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Define and explain the following 06

1. Enantiomers 2. Chirality 3. Conformations
(b) Describe sequence rules for the RS system of nomenclature 05
(c) Discuss Geometrical isomerism with examples 05
Q.2 (a) What is racemic mixture? Describe various methods for resolution of racemic 06
mixture
(b) Discuss synthesis, reactions and medicinal uses of oxazole 05
(c) Explain stereo selective reaction by giving examples 05
Q.3 (a) Explain Dakin reaction and Schmidt rearrangement with mechanism 06
(b) Describe conformational isomers of n-Butane 05
(c) Write structure of the following 05
1. 2-Methyl thiophene 4. 4-Chloro Pyrazole
2. Cis 2-Butene 5. 3-Nitro Pyridine
3. Furfural
Q.4 (a) Comment on the following 06
1. Thiophene is more aromatic than furan and pyrrole
2. Pyridine is stronger base than pyrrole
3. Pyridine undergoes electrophilic substitution at C3 Position
(b) Write in detail about conformations of cyclohexane 05
(c) Discuss the various methods of synthesis for quinoline 05
Q.5 (a) Write synthesis and medicinal uses of pyrimidines 06
(b) Discuss the atropisomerism in details 05
(c) Write the possible stereoisomers of the 2,3- Dichloro Butane with R and S 05
configuration
Q. 6 (a) Write any three methods of synthesis for pyrrole 06
(b) Write various reactions of pyridines 05
(c) Discuss the methods of synthesis for indole 05
Q.7 (a) Write a note on Clemmensen and Wolff kishner reduction with mechanism 06
(b) Discuss the any three reactions of thiazole 05
(c) Write synthesis, reactions and medicinal uses of acridine 05

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 Seat No.: _____ Enrolment No. _____________

GUJARAT TECHNOLOGICAL UNIVERSITY

B.Ph.- SEMESTER–IV • EXAMINATION – WINTER -2021

Subject Code: BP401TT Date: 23/02/2022

Subject Name: Pharmaceutical Organic Chemistry-III
Time: 02:30 PM to 05:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Discuss various methods for the synthesis of isoquinoline 06

(b) Write a note on Birch Reduction. 05
(c) Write various methods for the synthesis of indole and discuss fischer indole 05
synthesis with mechanism

Q.2 (a) Define following terms: 1. Optical activity 2. Enantiomers 3. Meso compound 06
(b) Discuss various methods for the synthesis of pyrimidine 05
(c) Describe Schmidt Rearrangement 05

Q.3 (a) Comments on the following 06

1. Thiophene is aromatic
2. Electrophilic substitution takes place at 2-position in
Pyrrole
3. Furan undergoes diels alder reaction
(b) Differentiate Stereospecific and Stereoselective reactions 05
(c) Discuss physical and chemical properties of pyrazole 05

Q.4 (a) Write methods for the preparation of thiazole 06

(b) Discuss the comparative basicity of Pyrrole, Pyridine and Aliphatic amines. 05
(c) Write methods for the preparation of thiophene 05

Q.5 (a) Write reactions of furan in detail 06

(b) Explain R and S configuration with example. 05
(c) Discuss any two methods for the synthesis of imidazole 05

Q. 6 (a) Write any two methods for the preparation of Quinoline 06

(b) Discuss atropisomerism for biphenyls 05
(c) Describe any one synthesis of purine and medicinal uses of purine 05

Q. 7 (a) What is resolution? Enlist different methods for resolution of racemic 06

mixture. Explain Conversion to Diastereomers method in detail.

(b) Write structures of the following 05

1) 2-Methyl thiophene 2) Furfural 3) Cis 2-butene
4) Oxazole 5) 2- Bromo Pyridine
(c) Define conformational isomers. Write a note on conformational isomerism of 05
Cyclohexane
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 GUJARAT TECHNOLOGICAL UNIVERSITY
B.Pharm - SEMESTER–4 • EXAMINATION – SUMMER - 2021

Subject Code: BP401TT Date:03/08/2021

Subject Name: PHARMACEUTICAL ORGANIC CHEMISTRY-III
Time: 10:30 AM to 01:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Define following terms. 06

1) Enantiomers 4) Atropisomers
2) Conformational isomer 5) Diastereoisomer
3) Heterocyclic compound 6) Chirality
(b) Write in detail about Resolution of Racemic mixture. 05
(c) What are Stereospecific and Stereoselective reactions? Explain in detail. 05
Q.2 (a) Explain in detail about Geometric isomerism with suitable examples and 06
describe method of determination of configuration of geometrical isomers.
(b) Describe Conformational isomerism of Cyclohexane. 05
(c) Write in detail about Stereochemistry of Biphenyl compounds. 05
Q.3 (a) Write in detail about methods of preparation of Pyrrole. 06
(b) Justify followings 05
1. Thiophene is more aromatic than Pyrrole and Furan.
2. Pyridine is more basic than Pyrimidine.
(c) Draw structure of following heterocyclic rings. 05
1. Piperazine 3. Isoquinoline 5. Piperidine
2. Pyrazine 4. Quinoxaline
Q.4 (a) Give different synthetiic methods of Pyrimidine in detail. 06
(b) Give application of Purine compounds in Pharmacy in detail. 05
(c) Write in detail about reactions of Pyrrole. 05
Q.5 (a) Describe Conformational isomerism of n-Butane 06
(b) Write a detailed note on Asymmetric synthesis. 05
(c) Describe Sequence rule with example for nomenclature of Optical isomers. 05
Q. 6 (a) Explain Clemmensen reduction in detail. 06
(b) Give synthetic methods of Thiazole in detail. 05
(c) Explain Oppenauer-oxidation reaction in detail. 05
Q.7 (a) Describe Fischer indole synthesis and give medicinal importance of Indole. 06
(b) Give different reactions of Chiral molecules. 05
(c) Write in detail about requirements to possess optical activity for a molecule. 05

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.PHARM - SEMESTER– IV EXAMINATION – WINTER -2020

Subject Code: BP401TT Date: 09/02/2021

Subject Name: PHARMACEUTICAL ORGANIC CHEMISTRY III
Time: 02:30PM TO 04:30PM Total Marks: 54
Instructions:
1. Attempt any THREE questions from Q-1 to Q-6.
2. Q.7 is compulsory to attempt.
3. Make suitable assumptions wherever necessary.
4. Figures to the right indicate full marks.

Q.1 (a) State and expalin Recemic mixure and write note on different methods of 06
resolution.
(b) Give the Preparation, Properties and Chemical reaction of Pyrrole. 05
(c) Give Difference between Enantiomers and Diesteriomers. 05
Q.2 (a) Give brief note on Conformation of Cyclohexane. 06
(b) State and Explain 05
a) Enantiomers b) Diesteriomers c) Specific rotation
d) Mesomers e) Geometric Isomer
(c) Write short note on preparation and chemical properties of Thiazole. 05
Q.3 (a) Give Brief note with mechanism on 06
a) Dakin Reaction b) Schmidt rearrangement
(b) Comment on following statements 05

i) Furan has high boiling point than Pyrrole.

ii) Furan is aromatic in nature although it containing two lone pair
electron.
iii) Thiophene is more aromatic than pyrrole.
iv) Electrophilic substitution on pyridine favour at C3 position.
v) Pyrrole is more basic than pyridine and aliphatic amine.
(c) Write a Short Note on Geometric Isomerism. 05
Q.4 (a) Write the Structure, Reaction, and Medicinal use of Imidazole, Oxazole. 06
(b) Give any three preparation of i) Indole ii) Quinoline 05
(c) Give Structure of following ring system 05
i) Pyrimidine ii) Isoquinoline iii) Purine iv) Acridine v) Thiazole
Q.5 (a) Give Brief note with Mechanism on 06
a) Clemmensen Reduction b) Beckmanns rearrangement
(b) Complete the reaction 05
H2SO4/HNO3
N
N
H
N
H2SO4

N
H
N
NaNH2

I2

N
H

(c) Explain Hantzsch Synthesis in detail with structural mechanism 05

Q. 6 (a) State and Explain and give brief note on Atropisomers with suitable examples. 06
(b) Write short note on preparation and chemical properties of Pyridine. 05

(c) State and explain with structural mechanism - Electrophilic substitution 05

reaction favour C2 position in Furan.
Q.7 (a) Give brief note on Claisen-Schmidt Condensation and Wolff Kishner 06
Reduction.
OR
(a) Explain in brief with suitable example - Stereospecific and Stereoselective 06
reactions.
OR
(a) Give brief note on reaction involve in LiAlH4 and NaBH4. 06

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.Ph. SEMESTER–IV • EXAMINATION – SUMMER -2020
Subject Code: BP401TT Date: 26-10-2020
Subject Name: Pharmaceutical Organic Chemistry III
Time: 10:30 AM TO 1:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Draw structure of the following compounds. 06

i) cis-3,4-dimethyl-3-heptene ii) trans-1,3-dichlorocyclobutane
iii) (R)-2-butanol iv) (RS)-2-chloro, 3-pentanol
v) cis- 2-chloro,3-bromo butene vi) (S)-3-chlorohexane
(b) Write note on stereochemistry of Biphenyls. 05
(c) What is resolution? Explain the methods for racemic modification into 05
enantiomers.
Q.2 (a) Define the following terms: 06
(i) Configuration (ii) Geometric isomerism (iii) Enantiomer
(iv) Meso isomer (v) Chiral center (iv) Racemic mixture
(b) Explain the reactions of chiral molecule. 05
(c) Explain Clemmensen reduction with mechanism. 05
Q.3 (a) Explain partial and absolute asymmetric synthesis. 06
(b) Explain diastereomers and their properties with suitable example. 05
(c) Write in brief conformational analysis of n-Butane. 05
Q.4 (a) Discuss the Sequence rule to assign configuration with example. 06
(b) Explain the stereospecific and stereoselective reactions. 05
(c) Give methods of determination of configuration of geometrical isomers. 05
Q.5 (a) Give the structure of: 06
(1) Indole (2) Pyridine (3) Isoquinoline
(4) Imidazole (5) Acridine (6) Thiophene
(b) Explain Beckmann rearrangement reaction with mechanism. 05
(c) Give synthesis and medicinal uses of Pyrimidine. 05
Q. 6 (a) Give THREE reactions of the following: 06
(1) Furan (2) Quinoline
(b) Write about Oppenauer oxidation. 05
(c) Comment on the following 05
1. Pyridine is more basic than Pyrrole.
2. Pyridine is less basic than aliphatic amines.
Q.7 (a) Write a short note on the following. 06
i) Skraup Quinoline synthesis
ii) Knorr pyrrole synthesis
(b) Explain metal hydride reduction by using different reagents. 05
(c) Explain preparation and reactions of Pyridine. 05

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.PHARM - SEMESTER– 4 EXAMINATION – WINTER -2019

Subject Code: BP401TT Date: 16-12-2019

Subject Name: Pharmaceutical Organic Chemistry-III
Time: 02:30 PM TO 05:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.
Seat No.: _____ Enrolment No. _____________

GUJARAT TECHNOLOGICAL UNIVERSITY

B.PHARM - SEMESTER– 4 EXAMINATION – SUMMER -2019

Subject Code: BP401TT Date: 06-05-2019

Subject Name: Pharmaceutical Organic Chemistry III
Time: 10:30 AM TO 01:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Define plane polarized light and discuss optical activity in detail. 06
(b) Differentiate enantiomers and diastereomers, discuss mesomers. 05
(c) Explain nomenclature of optical isomers. 05
Q.2 (a) Differentiate stereoselective and stereospecific reactions. 06
(b) Give short notes on nomenclature of geometrical isomers. 05
(c) Discuss the sequence rule in detail to assign configuration. 05
Q.3 (a) Discuss stability of various conformations of cyclohexane. 06
(b) Discuss stability of various conformations of n-butane. 05
(c) Explain stereoisomerism in biphenyl compounds. 05
Q.4 (a) Discuss basicity of pyridine. 06
(b) Draw the structures of imidazole, pyrazole, oxazole, thiazole and pyrrole. 05
(c) Discuss nomenclature and classification of thiophene and furan. 05
Q.5 (a) Explain any two synthesis and reactions of pyrrole. 06
(b) Discuss medicinal categories of thiophene and furan derivatives. 05
(c) Discuss electrophilic and chichibabin reaction of pyridine. 05
Q. 6 (a) Explain any two synthesis and medicinal uses of imidazole. 06
(b) Draw the structures of azepines and acridine and discuss any two reactions of 05
them.
(c) Discuss clemmensen reduction and birch reduction 05
Q.7 (a) Explain beckmanns rearrangement and Schmidt rearrangement. 06
(b) Discuss wolff kishner reduction and dakin reaction. 05
(c) Draw the structures of quinoline and isoquinoline and discuss any one synthesis 05
of both.

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.PHARM – SEMESTER – 4- EXAMINATION –WINTER - 2018

Subject Code:2240004 Date: 10/12/2018

Subject Name: Pharmaceutical Chemistry - VI (Organic Chemistry - II)
Time:02:30 PM TO 05:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make Suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.
Q.1 (a) Explain the following synthesis with reaction mechanism. 06
1. Fischer’s indole synthesis, 2. Skraup Quinoline synthesis.
(b) Define stereoselective and stereospecific reactions. Explain with suitable 05
examples.
(c) Enumerate different derivatives of carboxylic acids. How are they prepared from 05
carboxylic acids?
Q.2 (a) Comment on following. 06
1. Pyridine is less basic than aliphatic amines.
2. Thiophene is more basic than furan.
3. Trichloroacetic acid is more acidic than acetic acid.
(b) Explain Hell Wolhard Zelinsky reaction with mechanism. 05
(c) Write a note on Riemer Tiemann reaction. 05
Q.3 (a) Explain following terms giving suitable examples. 06
1. Configuration, 2. Chiral centre, 3. Mesomer,
4. Resolution, 5. Optical rotation, 6. Geometric isomers
(b) How is phenol prepared? Give any two methods. 05
(c) Write a note on conformational isomers of cyclohexane. 05
Q.4 (a) Give 1 preparation and 1 reaction of Thiophene, pyrrole, pyridine. 06
(b) Enumerate methods for preparation of carboxylic acid. Explain any two methods 05
from them.
(c) What is diazonium salt? Give their preparation and reactions. 05
Q.5 (a) Give structure of following compounds. 06
1. Pyrazine 2. Furan 3. Isooxazole
4. Pyrimidine 5. Indole 6. Pyridine
(b) Define nucleophilic aromatic substitution reaction. Explain benzyne mechanism. 05
(c) Write about application of nanochemistry in pharmacy. 05
Q. 6 (a) Define green chemistry. Explain the principles of green chemistry with suitable 06
examples.
(b) Write reaction and mechanism of aldol condensation. 05
(c) Give structure of following compounds. 05
1. Phenyl acetic acid, 2. para toluidine, 3. Benzoyl chloride
4. Malonic acid, 5. Phthalic anhydride.
Q.7 (a) Describe the principle of microwave synthesis. Explain applications of 06
microwave synthesis in chemistry.
(b) Define α,β-unsaturated carbonyl compounds. Explain Michael addition reaction 05
in detail.
(c) Explain Hoffmann degradation of amide in detail. 05

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GUJARAT TECHNOLOGICAL UNIVERSITY

B.Ph. - SEMESTER– IV• EXAMINATION – SUMMER 2018

Subject Code: 2240004 Date: 21/05/2018

Subject Name: Pharmaceutical Chemistry-VI (Organic Chemistry-II)
Time: 10:30 AM TO 01:30 PM Total Marks: 80
Instructions:
1. Attempt any five questions.
2. Make suitable assumptions wherever necessary.
3. Figures to the right indicate full marks.

Q.1 (a) Draw structure for the following compounds. 06

1) trans-1-bromo-3-chlorocyclobutane 2) cis-3-chloro-1-butene
3) 2-bromo-4-chloropentane 4) 3-chloro-2-butanol
5) (S)-3-chloro-1-pentanol 6) (2S,3R)-3-methyl-2-pentanol
(b) Write a Short note on stereochemistry of Biphenyls. 05
(c) Define the following terms: 05
i) Specific Rotation
ii) Racemic mixture
iii) Configuration
iv) Enantiomer
v) Geometrical isomerism

Q.2 (a) Explain the following reactions. 06

i) Kolbe reaction of Phenols
ii) Michael addition
(b) Discuss with mechanism Perkin reaction to synthesize α, β-unsaturated carbonyl 05
compounds.
(c) What are Phenols? How phenols are prepared? 05

Q.3 (a) What do you mean by Neucleophilic aromatic substitution reaction? Give 06
mechanism for Elimination –addition reaction for aryl halides.
(b) Explain the Hofmann degradation of amides. 05
(c) Explain the mechanism involved in Aldol condensation. 05

Q.4 (a) What do you mean by conformation? Discuss the stability and potential energy 06
changes of all conformations for n-pentane considering bond between C2 and C3.

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(b) How will convert the following. 05
i) Acetophenone to α-Phenyl ethyl alcohol.
ii) Benzoyl chloride to Ethyl benzoate
iii) Toluene to Benzylamine
iv) Toluene to o-Bromotoluene
v) Nitrobenzene to m-bromophenol
(c) What are Acid derivatives? Discuss the preparation and reactions of Esters. 05

Q.5 (a) Discuss the Neucleophilic addition reactions for carbonyl compounds. 06
(b) What are nano particles? How nano particles are used in Pharmacy. 05
(c) Give the structure of the following compounds: 05
i) 3,5-Dinitrobenzoyl Chloride
ii) p-hydroxyphenylacetic acid
iii) N,N-Dimethylaminocyclohexane
iv) o-Chloroanisole
v) Ethyl isopropyl ketone

Q.6 (a) What are heterocyclic compounds? Give the preparations and reactions of 06
pyridine.
(b) Give the structure of the following. 05
1) Pyrazine 2) Imidazole 3) Isoquinoline 4) Thiazole 5) Indole
(c) Comment on the following. 05
i) Electrophilic substitution in Pyrrole occurs at 2nd position rather than 3rd
position.
ii) Thiophene is more basic than furan.

Q.7 (a) Give preparation and reactions of diazonium salt. 06

(b) Write a note on green chemistry. 05
(c) Give applications of microwave synthesis in chemistry. 05

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