Chemical Energetics, Equilibria & Functional Organic Chemistry

Paper Code: 
24CCHY201
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

This course will enable the students to -

be acquainted with the laws of thermodynamics, chemical and ionic equilibria.

develop a perspective towards the mechanistic aspects of aromatic hydrocarbons, different alkyl halides and oxygen containing functional groups.

Course Outcomes (COs):

Course

Learning Outcome

(at course level)

Learning and Teaching Strategies

Assessment Strategies

Course Code

Course

Title

 

24CCHY 201

 

Chemical Energetics, Equilibria & Functional Organic Chemistry

(Theory)

 

CO13: Describe the laws of thermodynamics and apply them to calculate thermodynamic properties.

CO14:  Discuss the concept of chemical and ionic equilibria including Le Chatelier’s principle, equilibrium constants, ionization of an electrolyte and their applications.

CO15: Describe the mechanism of electrophilic and nucleophilic substitution reactions of aromatic substrates.

CO16: Explain the synthesis and reactivity of primary, secondary and tertiary monohydric alcohols, phenols, ethers and epoxides.

CO17: Predict the relative reactivities of different carbonyl compounds (aliphatic and aromatic aldehyde and ketones) and explain   their reactions.

CO18: Contribute effectively in course-specific interaction.

Approach in teaching:

Interactive lectures, tutorials, group discussions, e-learning.

 

 

 

Learning activities for the students:

Peer learning, e- learning, problem solving through tutorials and group discussions.

 

Written examinations, assignments and quiz. .

 

 

 

12.00
Unit I: 
Chemical Energetics

Review of thermodynamics and the first law of thermodynamics.

Joule-Thomson effect, Joule-Thomson coefficient for an ideal gas & real gas, inversion temperature. Important principles and definitions of thermochemistry. Concept of standard state and standard enthalpies of formations, integral and differential enthalpies of solution and dilution.

Calculation of bond energy, bond dissociation energy and resonance energy from thermochemical data. Variation of enthalpy of a reaction with temperature – Kirchhoff’s equation. Second and third law of thermodynamics, concept of entropy- entropy as a state function, entropy as a function of V & T, entropy as a function of P & T, entropy change in physical processes and calculation of absolute entropies of substances.

 

12.00
Unit II: 
Chemical and Ionic Equilibrium

Chemical Equilibrium: Free energy change in a chemical reaction, thermodynamic derivation of the law of chemical equilibrium. Distinction between ΔG and ΔGo, Le Chatelier’s principle. Relationships between Kp, Kc and Kx for reactions involving ideal gases.

Ionic Equilibria: Strong, moderate and weak electrolytes, degree of ionization, factors affecting degree of ionization, ionization constant and ionic product of water. Ionization of weak acids and bases, pH scale, common ion effect. Salt hydrolysis-calculation of hydrolysis constant, degree of hydrolysis and pH for different salts, buffer solutions. Solubility and solubility product of sparingly soluble salts – applications of solubility product principle.

 

12.00
Unit III: 
Aromatic hydrocarbons, Alkyl and Aryl Halides

Aromatic hydrocarbons: Aromaticity- Benzenoids and Hückel’s rule. Preparation (Benzene): from phenol, by decarboxylation, from acetylene, from benzene sulphonic acid.
Reactions (Benzene)- Electrophilic substitution, nitration, halogenation and sulphonation. Friedel-Craft’s reaction (alkylation and acylation) (upto 4 carbons on benzene). Side chain oxidation of alkyl benzenes (upto 4 carbons on benzene).

Alkyl Halides (Upto 5 Carbons): Types of nucleophilic substitution (SN1, SN2 and SNi) reactions and elimination reactions (E1, E2 and E1cB). Elimination vs  substitution. Preparation of alkenes from alcohols.
Reactions of alkyl halides- hydrolysis, nitrite & nitro formation, nitrile & isonitrile formation. Williamson’s ether synthesis.

Aryl Halides: Preparation from Phenol, Sandmeyer & Gattermann reactions.
Reactions (Chlorobenzene): Aromatic nucleophilic substitution (replacement by –OH group) and effect of nitro substituent. Benzyne Mechanism: KNH2/NH3 (or NaNH2/NH3). Reactivity and relative strength of C-Halogen bond in alkyl, allyl, benzyl, vinyl and aryl halides.

12.00
Unit IV: 
Alcohols, Phenols and Ethers (Upto 5 Carbons)

Alcohols: Preparation of 1о, 2о and 3о alcohols using Grignard reagent, ester hydrolysis, reduction of aldehydes, ketones, carboxylic acid and esters.

Reactions with sodium, HX (Lucas test), esterification, oxidation (with PCC, alk. KMnO4, acidic dichromate, conc. HNO3). Oppeneauer oxidation diols, oxidation of diols. Pinacol-Pinacolone rearrangement.

Phenols (Phenol only): Preparation- Cumene hydroperoxide method, from diazonium salts.

Reactions: Electrophilic substitution- Nitration, halogenation and sulphonation. Reimer-Tiemann Reaction, Gattermann-Koch Reaction, Houben–Hoesch Condensation, Schotten – Baumann Reaction.

Ethers (aliphatic and aromatic): Cleavage of ethers with HI.

 

12.00
Unit V: 
Aldehydes and ketones (aliphatic and aromatic)

Aldehydes and ketones (aliphatic and aromatic): (Formaldehye, acetaldehyde, acetone and benzaldehyde)                                                                                        Reactions – Comaparative reactivity of formaldehye, acetaldehyde, acetone and benzaldehyde, acid and base catalyzed mechanism of nucleophilic addition reaction, reaction with HCN, ROH, NaHSO3, NH2-G derivatives. Iodoform test. Aldol Condensation, Cannizzaro’s reaction, Wittig reaction, Benzoin condensation. Clemmensen reduction, Wolff Kishner reduction and Meerwein-Pondorff Verley reduction.

 

 

 

Essential Readings: 
  1. Principles of Physical Chemistry, Forty Eighth Edition; B. R. Puri, L. R. Sharma, M. S. Pathania; Vishal Publishing Co., Jalandhar, 2020. (Unit I)
  2. An Introduction to Chemical Thermodynamics, Sixth Revised Edition; R.P. Rastogi and R.R. Misra; Vikas Publishing House, 2015. (Unit II)
  3. Organic Chemistry; Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.

 

References: 
  1. Atkin’s Physical Chemistry, Eighth Edition; P.W. Atkins, J. Paula; Oxford University Press, International Student Edition, 2017.
  2. Thermodynamics for Chemist, S. Glasstone; East West Press, Private Limited, 2015.
  3. A Textbook of Physical Chemistry, Thermodynamics and Chemical Equilibrium, Vol. II, Sixth Edition; K. L. Kapoor; McGraw Hill Education Private Limited, 2019.
  4. Organic Chemistry, Second edition; J. Clayden, N. Greeves, S. Warren; Oxford University Press, United Kingdom, 2014.
  5. Organic Chemistry, Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  6. Organic Chemistry, Twelth Edition (Global Edition); T. W. Graham Solomons, C. B. Fryhle, S. A. Snyder; Wiley Publishers, United Kingdom, 2017.

 

e-Resources:

  1. https://nptel.ac.in/courses/112105123 (Unit I) https://www.uou.ac.in/sites/default/files/slm/BSCCH-103.pdf (see Block 4 for Unit-I)
  2. https://uou.ac.in/sites/default/files/slm/BSCCH-203.pdf (see Block 1 for Unit I & II)
  3. https://archive.nptel.ac.in/courses/103/103/103103144/ (Unit I & II)
  4. https://nptel.ac.in/courses/104103071 (Unit III, IV,V)
  5. https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro1.htm (Unit III, IV,V)
  6. https://ocw.mit.edu/courses/chemistry/5-12-organic-chemistry-i-spring-2003/lecture-handouts/ (Unit III, IV,V)

 

Academic Year: