Oxygen Containing Functional Groups

Teacher

Dr. Susanta Kumar Biswal

Category

Core Courses

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Course Name : Oxygen Containing Functional Groups

Code(Credit) : CUTM1474(3-2-1)

Course Objectives

  • The aim of this course to introduce basic practical skills to synthesize organic molecules containing functional groups like alcohols, acids, acid derivatives, carbonyl compounds, ethers, etc.
  • In addition to that, the course will also help students to understand the reaction mechanism subjects in the later stages of their study.

Course Outcomes

COs Course outcomes Mapping COs with POs (High-3, Medium-2, Low-1)
CO1 Students will have a firm foundation in understanding the fundamentals of organic chemistry and application of organic transformations. PO1 (3)
CO2 This helps students to gain experience to predict the functional group transformations, simple reaction mechanisms, and the synthesis of organic molecules by multi-step synthesis strategies PO2(3)
CO3 They will be able to design and carry out scientific experiments as well as accurately record and analyse the results of such experiments. PO3(2), PO4 (1)
CO4 Students will be able to explore new areas of research in both chemistry and allied fields of science and technology. PO3(2), PO5 (1), PO7(1)

Course Syllabus

Module-1

Chemistry of Alkyl Halides

Theory (4h)

  • Alkyl halides: Methods of preparation of Alkyl halides
  • Nucleophilic substitution Unimolecular (SN1) reaction
  • Nucleophilic substitution Bimolecular (SN2)reaction and SNi mechanism
  • Stereochemical aspects of SN1, SN2 and SNi reactions

Practice (2h)

  • Functional group test for Alkyl halides

Assignment (2h)

  • Nucleophilic substitution vs. Elimination.
  • Effect of solvent on SN1, SN2 reaction mechanism

Module-2

Aryl Halides and Organometallic compounds

Theory (4h)

  • Preparation of Aryl halides including preparation from diazonium salts
  • Nucleophilic aromatic substitution (SNAr) of aryl halides
  • Benzyne mechanism
  • Organometallic compounds of Mg and Li and use in the synthesis of organic compounds

Practice (4h)

  • Preparation of benzene diazonium chloride.
  • Synthesis of chlorobenzene from aniline

Assignment (2h)

  • Relative reactivity of alkyl, allyl /benzyl, vinyl and aryl halides towards nucleophilic substitution reactions.
  • Synthesis of organic compounds using organometallic compounds of Mg/Li.

Module-3

Alcohols

Theory (4h)

  • Preparation of Alcohols
  • Properties and relative reactivity of 1°, 2°, 3° alcohols, Bouvaelt-Blanc Reduction
  • Preparation and properties of glycols
  • Oxidation by periodic acid and lead tetraacetate

Practice (4h)

  • Functional group test for alcohol
  • Distinction between primary and secondary alcohols with tertiary alcohols

Assignment (1h)

  • Effect of  substituents on Pinacol-Pinacolone rearrangement

Module-4

Phenols, ethers and epoxides

Theory (4h)

  • Preparation and properties, Acidity and factors affecting the acidic character of Phenol
  • Ring substitution reactions, Reimer- Tiemann, Kolbe’s-Schmidt Reactions, Fries and Claisen rearrangements with mechanism
  • Preparation of Ethers and reactions with acids
  • Preparation of Epoxides

Practice (4h)

  • Functional group test for Phenol
  • Separating components of a mixture by extraction using Ether

Assignment (1h)

  • Reactions of epoxides with alcohol, ammonia derivatives, and LiAlH4.

Module-5

Carbonyl Compounds-1

Theory (4h)

  • Structure, reactivity, and preparation of carbonyl compounds, Nucleophilic additions
  • Nucleophilic addition-elimination reactions with ammonia derivatives with the mechanism
  • Mechanisms of Aldol and Benzoin condensation, Knoevenagel condensation, Claisen-Schmidt, Perkin, Cannizzaro reaction
  • Wittig reaction, Beckmann and Benzil-Benzilic acid rearrangement

Practice (4h)

  • Functional group test for Carbonyl compounds
  • Silver mirror test for carbonyl compounds

Assignment (1h)

  • Draw the mechanism of all the name reactions in this module

Module-6

Carbonyl Compounds-2

Theory (4h)

  • Haloform reaction and Baeyer Villiger oxidation, alfa- substitution reactions, oxidations and reductions (Clemmensen, Wolff-Kishner, LiAlH4, NaBH4, MPV, PDC )
  • Addition reactions of unsaturated carbonyl compounds: Michael addition, Active methylene compounds: Keto-enol tautomerism.
  • Preparation and synthetic applications of diethyl malonate
  • Preparation and synthetic applications of ethyl acetoacetate.

Practice (2h)

  • Haloform test for carbonyl compounds

Assignment (1h)

  • Reactivity order of Carbonyl compounds

Module-7

Carboxylic Acids and their Derivatives and Sulfer containing compounds

Theory (6h)

  • Preparation, physical properties, and reactions of monocarboxylic acids
  • Typical reactions of dicarboxylic acids, hydroxy acids, and unsaturated acids
  • Succinic/phthalic, lactic, malic, tartaric, citric, maleic and fumaric acids
  • Preparation and reactions of acid chlorides, anhydrides, esters, and amides
  • Preparation and reactions of thiols
  • Preparation and reactions thioethers
  • Preparation and reactions sulphonic acids

Practice (4h)

  • Functional group test for carboxylic acid
  • Hydrolysis of ester

Assignment (4h)

  • Comparative study of nucleophilic substitution at acyl group -Mechanism of acidic and alkaline hydrolysis of esters
  • Draw the mechanism of Claisen condensation, Dieckmann and Reformatsky reactions, Hofmann-bromamide degradation and Curtius rearrangement

Session Plan

Session 1 (Theory 1h)

  • Alkyl halides: Methods of preparation of Alkyl halides

Youtube link: Preparation of Alkyl halides

https://www.slideshare.net/ganeshmote1/alkyl-halide-131723782

Session 3 (Theory 1h)

  • Nucleophilic substitution Bimolecular (SN2)reaction and SNi mechanism

Youtube link: SN2 reactionSNi reaction

https://www.slideshare.net/born2beawinner/sni-substitution-reactions?qid=e0fccc4f-a2e9-4cf5-86d0-91e501e9bbdf&v=&b=&from_search=5

Session 4 (Theory 1h)

  • Stereochemical aspects of SN1, SN2 and SNi reactions

Youtube link: Stereochemistry of SN1 and SN2 mechanism

Session 5 (Practice 2h)

  • Functional group test for alkyl halides

Youtube link: Functional group test for halides

Session 6 (Flip class 1h)

  • Nucleophilic substitution vs. Elimination.

Session 7 (Flip class 1h)

  • Effect of solvent on SN1, SN2 reaction mechanism

Session 8 (Theory 1h)

  • Preparation of Aryl halides including preparation from diazonium salts

Youtube link: https://www.youtube.com/watch?v=GI0-1I92UB8

http://qu.edu.iq/edu/wp-content/uploads/2015/11/Aryl-Halides.pdf

Session 11 (Theory 1h)

  • Organometallic compounds of Mg and Li and use in the synthesis of organic compounds

Youtube link: Organolithium compoundsGrignard reagent

https://www.slideshare.net/UmangJagani1/grignard-reagents-83414779?qid=c0fdef70-938a-4951-b305-5a214d6c0998&v=&b=&from_search=3

Session 12 (Practice 2h)

  • Chlorobenzene from Aniline via the Sandmeyer Reaction

Youtube link: Chlorobenzene from Aniline via the Sandmeyer Reaction

Session 13 (Practice 2h)

  • Preparation of benzene diazonium chloride

Youtube link: Preparation of benzene diazonium chloride

Session 14 (Flip class 1h)

  • Relative reactivity of alkyl, allyl /benzyl, vinyl and aryl halides towards nucleophilic substitution reactions

Session 15 (Flip class 1h)

  • Synthesis of organic compounds using organometallic compounds of Mg/Li.

Session 17 (Theory 1h)

  • Properties and relative reactivity of 1°, 2°, 3° alcohols, Bouvaelt-Blanc Reduction

https://www.slideshare.net/mizakamaruzzaman/chapter-1-alcohols

Reference: https://www.youtube.com/watch?v=LwHCKLTZr3M

Session 19 (Theory 1h)

  • Oxidation by periodic acid and lead tetraacetate

Youtube link: https://www.youtube.com/watch?v=iiylAnpVHu0

https://www.youtube.com/watch?v=1S29grjAoyA

Session 20 (Practice 2h)

  • Functional group test for alcohols

Youtube link: Test for alcohols 

Session 21 (Practice 2h)

  • Distinguish between alcohols; Oxidation Test: primary & secondary from tertiary

Youtube link: Oxidation Test: 1-ary & 2-ary from 3-ary alcohol

Session 23 (Theory 1h)

  • Ring substitution reactions, Reimer- Tiemann, Kolbe’s-Schmidt Reaction, Fries and Claisen rearrangements with mechanism

Youtube link:https://www.youtube.com/watch?v=5VhwkoP3fsE 

https://www.youtube.com/watch?v=LgZcOxps0jQ

https://www.youtube.com/watch?v=NIxEX4F0UY0

https://www.youtube.com/watch?v=6qiBBRBIlN0

Reference: https://www.youtube.com/watch?v=Pmv5HYICotY

https://www.youtube.com/watch?v=Upi8UJgwnPo

Session 26 (Practice 2h)

  • Functional group test for phenols

Youtube link: Test for phenols

Session 27 (Practice 2h)

  • Separating Components of a Mixture by Extraction

Youtube link: https://www.youtube.com/watch?v=N96JaRnE7n0

Session 28  (Flip class 1h)

  • Reactions of epoxides with alcohol, ammonia derivatives, and LiAlH4

Session 30 (Theory 1h)

  • Nucleophilic addition-elimination reactions with ammonia derivatives with mechanism

Youtube link: https://www.youtube.com/watch?v=15A19Ndtg5g

Session 31 (Theory 1h)

  • Mechanisms of Aldol and Benzoin condensation. Knoevenagel condensation, Claisen-Schmidt, Perkin, Cannizzaro reaction

Youtube link:https://www.youtube.com/watch?v=bVcHiDSvrO0

https://www.youtube.com/watch?v=JNkEm-8CN3U

https://www.youtube.com/watch?v=jjLUiw1i4eM

https://www.youtube.com/watch?v=vB_ARt2tJ4o

Reference: https://www.youtube.com/watch?v=OBT3otCRBxg

Session 33 (Practice 2h)

  • Functional group test for Carbonyl compounds

Youtube link: Functional group test for Carbonyl compounds

Session 34 (Practice 2h)

  • Silver mirror test for carbonyl compounds

Youtube link: Silver mirror test for carbonyl compounds

Session 35 (Flip class 1h)

  • Draw the mechanism of all the name reactions in this module

Session 36 (Theory 1h)

  • Haloform reaction and Baeyer Villiger oxidation. alfa- substitution reactions, oxidations and reductions (Clemmensen, Wolff-Kishner, LiAlH4, NaBH4, MPV, PDC)

Youtube link: https://www.youtube.com/watch?v=mTQDrFsTGvQ

https://www.youtube.com/watch?v=Umvw5ZkFdRw

https://www.youtube.com/watch?v=Pp0LeL0SkRg

Session 37 (Theory 1h)

  • Addition reactions of unsaturated carbonyl compounds: Michael addition. Active methylene compounds: Keto-enol tautomerism.

Youtube link: https://www.youtube.com/watch?v=CBLx2vchUiA

https://www.youtube.com/watch?v=Th-YjaG3kcc

Session 38 (Theory 1h)

  • Preparation and synthetic applications of diethyl malonate

Youtube link: https://www.youtube.com/watch?v=7O_kWGVdbe4

Session 39 (Theory 1h)

  • Preparation and synthetic applications of ethyl acetoacetate.

Youtube link: https://www.youtube.com/watch?v=CL5uUUpgYC8

Session 40 (Practice 2h)

  • Haloform(Iodoform) test for carbonyl compounds

Youtube link: Iodoform test

Session 41 (Flip class 1h)

  • Reactivity order of Carbonyl compounds

Session 48 (Practice 2h)

  • Functional group test for carboxylic acid

Youtube link: functional group test for carboxylic acid

Session 49 (Practice 2h)

  • Ester Hydrolysis

Youtube link: Hydrolysis of ester

Session 50 (Flip class 1h)

  • Comparative study of nucleophilic substitution at acyl group 

Session 51 (Flip class 1h)

  • Mechanism of acidic and alkaline hydrolysis of esters

Session 52 (Flip class 2h)

  • Draw the mechanism of Claisen condensation, Dieckmann and Reformatsky reactions, Hofmann-bromamide degradation and Curtius rearrangement

 

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