CHEM 145; Fundementals of Organic Chemistry

  • Introduction (Bonding, Structural Formulas, and Molecular Shapes); (2Lect.)

Organic Chemistry (definition), The Uniqueness of Carbon, Atomic Structure, Chemical Bonds (ionic, Covalent), Acid-Base concept. Atomic and Molecular orbital, Hybridization, Bond Energy (definition) and Bond Length, Hybridization, Polarity and Inductive effect, Functional groups; Hydrocarbon Compounds (Aliphatic (saturated & unsaturated) and Aromatic).
 

  • Alkanes, Cycloalkanes; (3Lect.)

Alkanes;
Structure, Structural Isomerism, Classes of Carbons and Hydrogen (1°, 2° & 3°), Alkyl groups, IUPAC nomenclature, Physical properties (physical state, solubility, boiling point & melting point), Sources, Preparation [Wurtz reaction. Reduction of alkyl halides using lithium dialkyl cuprate], Notations for Bond Breaking and Bond Making (free radical, carbocation, carbanion), Reactions (Combustion, Halogenations), Mechanism of Halogenation of Alkanes,
Cycloalkanes;
Nomenclature, ring strain effect of three- and four-membered ring, reactions of cyclopropane and cyclobutane (hydrogenation and halogenation).
 

  • Alkenes; (2Lect.)

IUPAC nomenclature, Physical properties, Geometrical isomerism of alkenes (cis, trans), Synthesis [Dehydration of alcohols; (Saytzeff’s Rule, Classes of Carbocations and Ease of Dehydration of Alcohols), Dehydrohalogenation of Alkyl Halides & dehalogenation of vicinal dihalide using Zn and acetic acid], Reactions [Addition reactions of Alkenes (Hydrogenation, Halogenations), Electrophilic Addition to Alkenes– Markovnikov’s rule (Addition of Hydrogen Halide, Hydration, Halohydrin formation), Oxidation of Alkenes (KMnO4 and Ozonolysis). Applications (recommended)
 

  • Alkynes; (2Lect.)

IUPAC nomenclature, Physical properties, Acidity of terminal alkynes, Synthesis (Dehydrohalogenation, from vicinal dihalides, and Reaction of Sodium Acetylide with Primary Alkyl bromide). Reaction (Hydrogenation, Halogenation, Addition of Hydrogen Halide, Hydration).
 

  • Aromatic Compound; (3Lect.)

Structure of Benzene, Stability of Benzene (Resonance Energy), Aromaic character, Hukel rule, Nomenlature (Mono-, Di- and Tri-substituted Benzenes), Electrophilic aromatic substitution reactions (Alkylation, Acylation, Halogenation, Sulphonation, Nitration), The Role of Catalysts, Side chain Reactions (halogenations and oxidation of an Alkyl Side Chain). Reactivity and Orientation in monsubstituted benzenes derivatives.
 

  • Week 7: 1st Midterm Exam

 

  • Alkyl halides; (2Lect.)

IUPAC nomenclature, classification (Alkyl halides, Vinylic halides. Allylic halides, Benzylic halides, Aryl halides), Physical properties (Solubility, Density, Boiling points), Synthesis [Direct halogenation of hydrocarbons, alcohols (with HCl, PCl3,PCl5,SOCl2)], Reactions of Halogen Compounds Nucleophilic substitution (CN-, HO-, NH3,…….), Elimination Reactions, Formation Uses of Organometallic Compounds (Grignard reagents).
 

  • Alcohols and Phenols; (3Lect.)

IUPAC nomenclature, classification, Physical properties (Alcohols, hydrogen bonding, Diols and Triols, Acidity). Preparation (Hydration of Alkenes & Reduction of aldehydes, ketones, acids, and esters & addition of Grignard compound to aldehydes and ketones. Reactions Involving Carbon-Hydroxyl Bond Breaking (Formation of esters, Replacement of the OH Group by Halide, Dehydration of Alcohols. Reactions involving breaking of O-H bond.
Preparation of Phenols (The Alkali Fusion of Sulfonates & hydrolysis of diazonium salt). Reactions (Salt Formation, Oxidation). Reactions on the Aromatic Ring of Phenols
 

  • Ethers and Epoxides: (2Lect.)

Structure of Ethers (symmetrical and unsymmetrical ethers), Nomenclature, Physical properties. Synethsis of ethers (dehydralion of alcohols, Wiliamson Synthesis). Reactions (Reaction with Cold and hot Concentrated Acids: HI), Cyclic Ethers, Uses of ethers.
Epoxides (synethsis from alkene using peracid, Ring opening, Reactions (-NH2, -OH, H3O+ and Grignard reagent).
 

  • Aldehydes and Ketones; (2Lect.)

Structure, Nomenclature, Physical properties. The Carbonyl Group, Physical Properties (boiling points, dipole-dipole attraction, Solubility). Synthesis (Oxidation of Primary and Secondary Alcohols, Ozonolysis of Alkenes, Hydration of Alkynes, Friedel-Crafts Acylation). Reactions: Nucleophilic addition [Addition of Metal Hydrides (LiAlH4 & NaBH4), Addition of Grignard Reagents (Formation of Alcohols), Addition of Hydrogen Cyanide (Formation of Cyanohydrins), Addition of Alcohols (Formation of Hemiacetals and Hemiketals & Acetals and Ketals), Addition of Amines.
 

  • Week 14: 2nd Midterm Exam.

 

  • Carboxylic acids; (2Lect.)

Structure, Nomenclature, Physical properties, Acidity, Synthesis [Preparation of Acids by Oxidation; Oxidation of Primary Alcohols or Aldehydes, Oxidation of Alkylbenzenes), Carbonation of Grignard Reagents, Hydrolysis of Nitriles], Reactions (Salt Formation, Reduction, Esterification, Formation of Amides, Acid halides and Acid anhydrides).
 
Carboxylic Acid Derivatives
Acid halides, Esters, Amides, Acid anhydrides
Nomenclature, Sources and Uses of Esters, Reactions of Esters (Acid-Catalyzed Hydrolysis of Esters, Alkaline Hydrolysis of Esters (Saponification), Reduction of Esters).
 

  • Amines; (1Lect.)

Structure and Classification of Amines, Nomenclature, Physical properties, Basicity of Amines, Synthesis: (Reduction of nitriles, amide and nitro compounds), Alkylation of Ammonia, Reactions of Amines (Salt Formation, Alkylation, Amide and Imine Formation), Formation and conversion of diazonium salts, Azo Compounds.
 

  • Final revision
  • Final Exam.

 

  • Refernces:
  1. Organic chemistry: A short course by I Harold Hart, David J. Hart and Leslie E. Craine, Houghton Mifflin Company, 9th ed. USA.
  2. أسس الكيمياء العضوية - أ.د./ سالم بن سليم الذياب - الناشر: مؤسسة نافثة
Course Materials