Organic Chemistry: Course Outcome

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  • Topic: Carbonyl, Ester, Carboxylic acid
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UNIVERSITI TEKNOLOGI MARA COURSE INFORMATION Confidential
Code Course Level Credit Hours Contact Hours : : : : : CHM 556 Organic Chemistry II Degree 4 3 hr (Lecture) 3 hr (Practical) 3 Core CHM 456

Part Course Status Pre-requisite

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Course Outcomes

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Upon completion of this course, students should be able to: 1. Determine functional groups present in organic compounds using Infrared Spectroscopy and interpret Nuclear Magnetic Resonance spectra and relate the information to structural features of organic compounds. State and explain principles governing the physical and chemical properties of aldehydes, ketones, carboxylic acid, carboxylic acid derivatives and amines. Write, explain and solve problems related the reaction mechanisms for nucleophilic addtition of carbonyl compounds and nucleophilic acyl substitution of carboxylic acids and their derivatives. Develop synthetic methods for preparations of various types of aldehydes, ketones, carboxylic acids, carboxylic acid derivatives and amines. Plan, conduct, observe and report experiments in organic chemistry

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Course Description

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This course is a continuation of the study of organic chemistry begun in Organic Chemistry I. This course begins with an introduction to the use of infrared and nuclear magnetic resonance (NMR) spectroscopy in the determination of the structures of organic molecules. The chemistry and physical properties of carbonyl containing compounds such as aldehydes, ketones, carboxylic acids and carboxylic acid derivatives forms the major part of the course. Reactions involving enolate anions as nucleophiles are discussed. The emphasis of this course is on the development of problem solving skills in the context of structure features, synthesis and mechanism of reactions of carbonyl compounds. The chemistry of amines and overview of carbohydrate are also included. Syllabus Contents 1.0 Spectroscopy of Carbon Compounds 1.1 1.2 1.3 2.0 Introduction to Spectrocopy and Structural Identification Infrared Spectroscopy Proton and Carbon-13 Nuclear Magnetic Resonance Spectroscopy

Aldehydes and Ketones I: Oxidation, Reduction and Synthesis 2.1 2.2 Introduction: Nomenclature; Physical properties Reduction 2.2.1 Catalytic Reduction 2.2.2 Hydride Reducing Reagents: NaBH4, LiAlH4 2.2.3 Complete Removal of Carbonyl group; Clemmensen and Wolf-Kishner Reduction Synthesis of Aldehydes and Ketones Through Reduction of Acid Chlorides and Esters 2.3.1 Rosenmund Reduction 2.3.2 DIBAL-H Synthesis of Aldehydes through Oxidation of Alcohols o o 2.4.1 Oxidation of 1 and 2 Alcohols 2.4.2 Jones, Sarret and PCC Reagents 2.4.3 Tollen’s Test

2.3

2.4

3.0

Aldehyde and Ketone II: Nucleophilic Additions to the Carbonyl Group 3.1 3.2 3.3 3.4 3.5 Reactivity of Carbonyl Group; Nucleophilic Addition Cyanohydrin Formation; Synthesis of α-hydroxy acids and hydrolysis of nitriles Addition of Organometallic Reagents; Grignard and alky lithium reagents Addition of Water; Hydrates Addition of Alcohols; Acetals and Hemiacetals 3.5.1 Cyclic Acetals 3.5.2 Protecting Group using Acetals Addition of Amines 3.6.1 Imines from 1o Amines 3.6.2 Enamines from 2o Amines 3.6.3 Enamines for Alkylation of Ketones Wittig Reaction

3.6

3.7

4.0

Carbohydrates 4.1 4.2 4.3 4.4 4.5 4.6 Carbohydrate Structures; Fischer Projections; D and L Notations Cyclization of Monosaccharides; Furanose and pyranose rings Haworth Projections and Chair Forms; Anomers Converting Fischer Projections to Haworth Projections Mutarotation Reactions of Carbohydrates 4.6.1 Reduction and Oxidation 4.6.2 Conversion to Acetal; Formation of glycosides Disaccharides and Polysaccharides

4.7 5.0

Carboxylic Acids 5.1 5.2 Nomenclature; Physical Properties Synthesis of Carboxylic Acids 5.2.1 Oxidation of 1o Alcohols 5.2.2 5.2.3 5.2.4 5.3 Side chain Oxidation of Aromatic Compounds Carbonation of Grignard and Alkyl Lithium Compounds Hydrolysis of Nitriles

5.4 6.0...
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