CHEMISTRY 214

Organic Chemistry II

Organic Chemistry II continues the systematic examination of the reactions of common functional groups that were featured in Chem 213. Aromatic compounds including phenols, carbonyl condensation reactions, carboxylic acids and their derivatives are studied. Biological topics include amino acids, peptides, proteins, phospholipids, terpenes, steroids, nucleic acids and the Krebs Cycle. Spectroscopy is studied and the importance of spectroscopic techniques in the analysis of organic compounds is emphasized. These techniques will be used in the laboratory component of the course. With Chem 213, this course satisfies organic chemistry requirements for students pursuing careers in chemistry, biology, biochemistry, home economics, forestry, premedicine and pharmaceutical science.

Chemistry 213

Course content varies by instructor. An example of course content might be:

Aromatic Compounds:

• Electrophilic substitution (nitration, alkylation, halogenation, sulphonation), mechanism and effect of substituents on rate and position of substitution.
• Side chain derivatives.

• Structure and nomenclature,
• Physical properties (H-bonding, acidity - contrast with alcohols and acids),
• Preparations and reactions (ring substitution, ether formation, effect of ring substitution on acidity).

Spectroscopy:

• Mass spectrometry - interpretation of spectra for alkanes and alkyl fragments, and the behaviour of common functional groups.
• Infra-red - bond stretching and bending, identification of major functional groups by stretching and bending modes (C-H, C-O, C-C, O-H, COOH, N-H, N-O.
• PMR - basic concepts, shielding, chemical shift, spin-spin coupling, application to spectra. Determination of unknown structures by ir and pmr spectroscopy.
• General application to lab work.

• Review of nomenclature.
• Preparation (oxidation, Grignard reagents, hydrolysis of nitriles).
• Structures of acids and acid derivatives.
• Acidity.
• Nucleophilic acyl substitutions to acids and their derivatives using reaction mechanisms. Use of acids and derivatives in multi-step syntheses.
• Reactions (conversion to esters, amides, anhydrides, acid chlorides). *fats, oils, soap and detergents.

• Carbonyl condensation reactions, Condensation - aldol, crossed, aldol, Claisen,
• Use of crossed aldol reactions in multi-step syntheses,
• Malonic acid and acetoacetic ester syntheses.

• Nomenclature, preparation (reduction of nitro compounds, alkylation, reductive amination, reduction of nitriles, Gabriel method.
• Basicity and effect of ring substitution of electron donating and electron withdrawing groups on the basicity of aromatic amines.
• Reactions of amines with alkyl halides, benzene sulphonyl chloride, and nitrous acid.
• Use of diazonium compounds in multi-step syntheses and in coupling reactions.
• Sulphanilamide and sulpha drugs: synthesis and function.

• Structures and nomenclature of amino acids,
• Isoelectric point, cationic, anionic, and zwitterionic forms,
• Synthesis of amino acids by ammonolysis, amination, (Strecker synthesis), modified Gabriel and Gabriel/Malonic ester methods. Peptide and protein structures,
• Dipeptide and polypeptide syntheses, use of protecting group, coupling,
• Merrifield automated protein synthesis,
• Analysis by Edman or Sanger degradation, partial hydrolysis, sequencing.

Phospholipids, Terpenes and Steroids:

• Mainly structural details.

Nucleic acids:

• Structure of nucleotides, A/T/G/C, phosphate esters, pka of phosphate, base-pairing in DNA and RNA.

• Study of glycolysis and Krebs Cycle to demonstrate biochemical efficiency,
• Study of Krebs Cycle to illustrate previously discussed reactions:a) aldol condensation, (b) dehydration, (c) hydration, (d) oxidation, and (e) decarboxylation.

1. Synthesis and Separation of Ortho- and Para-Nitrophenols (two week);
2. Infra-red Spectroscopy: Liquid and solid Samples;
3. Synthesis of a Carbonyl Compound (vacuum distillation): Synthesis of Sulcatol;
4. Qualitative Organic Analysis: Sodium Fusion and Functional Group Tests;
5. Carboxylic Acids and their Derivatives (amide and anilide);
6. Syntheses of Amines (tribromoaniline, p-bromoacetanilide, p-bromoaniline) (two week) Aromaticity, Huckel's rule, common aromatic heterocyclic compounds;
7. Reactions of Amines: Characterization by Derivative Formation and Identification;