CHE (Organic) P-502 : Advanced organic synthesis (Semester 3 )

CHE(O) 502  

Advanced organic synthesis

-M.SC Syllabus  Gujarat University 2021-22

Unit-I- PCR and Conformational analysis

• Introduction & classification, 
• Electrocyclic reactions - introduction,
• definition and classification,
• Woodward-Hoffmann rules for electrocyclic reactions,
• Stereochemical aspects and modes of electrocyclic reactions,
• Cycloaddition reactions,
• Woodward- Hoffmann rules for cycloaddition reactions,
• Examples of thermal and photochemical [2p+2p] cycloaddition
• reactions,
• 1,3-Dipolar cycloaddition reactions,
• higher order cycloaddition reactions,
• Sigmatropic rearrangements - examples,
• Claisen and Cope rearrangements,
• Conformation and Configuration,
• Barriers to rotation,
• Conformation of ethane,propane, butane,Ring strain,
• Ring inversion of cyclohexane,
• Substituted cyclohexane,
• Decalins 

Unit-II- Protecting groups

• Role of protecting group in organic synthesis,
• principle of protection of hydroxyl (alcohol and phenol), amino [amine – (primary, secondary) and amide], carbonyl (ketone and aldehyde),
• carboxylic acid with different (minimum 5) reagents and their deprotection, 
• synthetic equivalent groups (application of protection & deprotection approach with proper organic reaction). 

Unit-III Retrosynthesis

• Introduction and terminology,
• guidelines for disconnections,  
• functional group inter- conversions, 
• The importance of the order of events in organic synthesis,
• Chemo selectivity,
• One group C-X and two group C-X disconnections,
• Natural reactivity’ and ‘umpolung’, (epoxide, Haloketones and esters, 1,3 dithiane, cynide, Nitro, alkynes) 
• C-C disconnection: Introduction, Alcohols, and carbonyl compounds, regioselectivity, alkene synthesis, use of acetylenes and aliphatic nitro compounds in organic synthesis.

Unit IV: Oxidation-Reduction

 Oxidation:

•  Introduction,
•  oxidation of hydrocarbons (alkanes, alkenes, aromatic ring),
•  phenol,
•  alcohols and diols,
•  ketones (aldehydes, carboxylic acids and their derivatives),
•  amines, hydrazine and sulphides.

 Reduction:

•  Introduction,
•  reduction of hydrocarbons (alkenes, alkynes, aromatic ring),
•  ketones (aldehydes,carboxylic acids and their derivatives, esters),
•  anhydrides,
•  nitrile,
•  epoxides,
•  nitro,
•  nitroso,
•  azo and oxime groups 

---

---

Learning objective:

1. To understand the reaction mechanism of a chemical reaction, the path andthe feasibility of a reaction.
2. To suggest synthetic route for complex organic compounds with stereochemistry. 
3. To understand the techniques involved in the determination of mechanism of reacted ions and to propose methods to determine the mechanism of reaction.
4. To make the students understand and appreciate the concept of Stereochemistry and reaction mechanism.

Learning Outcomes:

1. Learner can understand deep aspects of retrosynthesis and oxidationreduction reaction.
2. Learner can understand synthesis of the important organic molecule.
3. Learner can be able to design new molecules of interest.
4. PCR and Conformational analysis can give understanding of how the reactions take place by bond shifting and geometry.
5. Protection groups concept is important to synthesized desired compounds to avoid side reaction/products during organic synthesis.