Oxygen Containing Functional Groups

Teacher

Dr Anupam Sahoo

Category

Core Courses

Course Attendees

Still no participant

Course Reviews

Still no reviews

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.

Learning Outcomes

  • This course will build up a solid foundation for students which will definitely give road maps in basic organic chemistry.
  • It will really help students for higher study especially for research where one can apply this fundamental chemistry in making new drug molecules against various diseases.
  • Thus, it will enhance the chances for students to get into the pharmaceutical industry.

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

Recent Comments

     

    Our Main Teachers

    Dr Anupam Sahoo

    Assistant Professor
    VIEW PROFILE

    Organic Chemistry, Nanocomposites