CHEM 234          2 Credit Hours

Organic Chemistry II

This information is for second semester 2017/2018 academic year

Teacher responsible

Course content

This course introduces the student to some important functional groups in Organic Chemistry. It involves treatment of the structures and naming systems of these functional groups. The course also treats the properties of these compounds, their preparations, reactions including mechanisms and some applications. Simple identification tests for these functional groups are also considered. The similarities and differences between the aldehydes and ketones on one hand and the carboxylic acids and their derivatives on the other are extensively looked at.

Aldehydes and ketones  7 hr

• Nomenclature; structure of the carbonyl group; physical properties; laboratory methods of preparation.
• Nucleophilic addition reactions: hydration, cyanohydrin formation, acetal formation, acetals as protecting groups, thioketals as protecting groups (formation and removal), addition of sodium bisulphite, ammonia and its derivatives – discuss the reversibility of these reactions and their use for purification and identification.
• Some other reactions of aldehydes and ketones: Wolf-Kishner and Clemmensen reductions; formation and addition of Grignard reagents and organolithium compounds; reduction to alcohols; oxidation; designing simple syntheses.
• Carbanions: aldol condensation; iodoform reaction; Cannizzarro reaction.

Carboxylic acids 3 hr

• Nomenclature (dicarboxylic acids included); structure; general properties.
• Preparations: carbonation of Grignard reagents, hydrolysis of nitriles, oxidation of primary alcohols, oxidation of aldehydes and ketones.
• Reactions: acidity of carboxylic acids as compared to alcohols; separation of carboxylic acids; decarboxylation of carboxylic acids; reduction.

Carboxylic acid derivatives 5 hr

• Nomenclature of carboxylic acid derivatives; general properties.
• Carboxylic acid derivatives and nucleophilic substitution as compared to nucleophilic addition in aldehydes and ketones.
• Preparation of acid chlorides, anhydrides, esters and amides from carboxylic acids; interconversion of derivatives; comparison of nucleophilic attack on the derivatives; reduction of derivatives; transesterification.
• Introduction to polymers: Polyesters, synthetic polymers, amino acids and proteins.

Amines 5 hr

• Nomenclature; general properties.
• Preparations: Reduction of nitro compounds, reductive amination, reduction of nitriles; reduction of imines and oximes; reactions of ammonia and amines with alkyl halides; Hofmann degradation (mechanism).
• Reactions: Salt formation; nucleophilicity of amines in alkylation; quaternary ammonium salts; reactions of amines with benzenesulfonyl chloride (Hinsberg test); reactions of primary amines with nitrous acid; Hofmann elimination.

Teaching

The course is taught through lectures, class discussion and weekly tutorials to enhance students’ understanding of topics treated.

Formative coursework

There will be at least one major interim assessment (IA) and a final exam at the end of the semester. Students are expected to undertake presentations which will contribute to their final grades. The IA will be on the materials covered during lectures. Success in this course depends on reading widely on the topics to be treated, and is highly recommended.

Indicative Reading

Solomons, G.T.W., Fryhle, C.B. and Synder, S. C., (2011). Organic Chemistry.  John Wiley and Sons.

Loudon, G. M., (2009). Chemistry of Organic Compounds 3rd Edition. Roberts and Company Publishers.

Schmid, G. H., (1996). Organic Chemistry. Mosby Publishers. St. Louis, Missouri.

Vollhardt, K. P. C., Schore, N. E., (2007). Organic Chemistry, Structure and Function, 5th Edition, W. H. Freeman & Co., New York.

Wade Jr., L.G., (2013). Organic Chemistry, 9th Edition, Pearson, Boston.Glodstein, J.S. (1994).  International Relations.  Harper Collins College Publishers.

Assessment and Grading

• Mid-semester test/continuous interim assessment:   20%
• Presentation:                                                              10%
• Final Examinations:                                                   70%
• Total:                                                                        100%

Grading Scale: