Plants have been used for medicinal purposes throughout human history. In traditional Chinese medicine sweet wormwood leaves were brewed with water and used to treat fever. Bundjalung Aboriginal people from the coast of New South Wales crushed tea tree (Melaleuca alternifolia) leaves and applied the paste to wounds and skin infections. In medieval times, people brewed a tea from Willow bark and used it to ease aches and pains.

In the early 1800s the active ingredient of Willow bark was identified as salicylic acid. It was considered an effective analgesic, however a tendency to cause stomach bleeding seriously limited its usage. Felix Hoffmann, a German chemist, has been credited with the synthesis of aspirin in 1897. Aspirin (acetylsalicylic acid) is a derivative of salicylic acid which maintains analgesic effects whilst being easy on the stomach. Today aspirin is one of the most used drugs in the world.

This program will best suit students who understand basic organic chemistry, in particular functional groups and IUPAC nomenclature.

Students will:

• Consolidate their understanding of functional groups and organic reactions
• Practice identifying key peaks in IR spectra
• Analyse HPLC data using a calibration curve
• Develop their wet laboratory skills and identify common sources of experimental error

Students will:

• Perform an esterification reaction
• Use an infrared spectrometer to identify functional groups in unknown organic compounds
• Prepare an analgesic tablet and run it through a HPLC machine to identify whether the tablet contained aspirin or paracetamol.
• Quantify the amount of aspirin or paracetamol in their tablet using a calibration curve and appropriate formula

Ecolinc Learn Online is a virtual outreach learning management system (LMS) offering interactive online courses for students and teachers. These courses can be undertaken either as a pre-visit, post-visit or stand-alone.

Students are encouraged to do the pre-learning course on Ecolinc Learn Online called Safe Labs prior to coming to Ecolinc. In this course students will cover all the necessary aspects of laboratory safety during their time at Ecolinc. When planning any work in a laboratory the risk of exposure to laboratory hazards is an important consideration. This course is part of Ecolinc’s risk minimisation for student safety.

Area of Study 1: How are organic compounds categorised and synthesised?

Structure, nomenclature and properties of organic compounds

• Characteristics of the carbon atom that contribute to the diversity of organic compounds formed, with reference to valence electron number, relative bond strength, relative stability of carbon bonds with other elements, degree of unsaturation, and the formation of structural isomers
• Molecular, structural and semi-structural (condensed) formulas and skeletal structures of alkanes (including cyclohexane), alkenes, benzene, haloalkanes, primary amines, alcohols (primary, secondary, and tertiary), aldehydes, ketones, carboxylic acids and non-branched esters
• The International Union of Pure and Applied Chemistry (IUPAC) systematic naming of organic compounds up to C8, with no more than two functional groups for a molecule, limited to non-cyclic hydrocarbons, haloalkanes, primary amines, alcohols (primary, secondary, tertiary), aldehydes, ketones, carboxylic acids and non-branched esters.

Reactions of organic compounds

• Organic reactions and pathways, including equations, reactants, products, reaction conditions and catalysts (specific enzymes not required):
  • synthesis of primary haloalkanes and alcohols by substitution
  • addition reactions of alkenes
  • the esterification between and alcohol and carboxylic acid
  • hydrolysis of esters
  • pathways for the synthesis of primary amines and carboxylic acids

Area of Study 2: How are organic compounds analysed and used?

Instrumental analysis of organic compounds

• Identification of bond types by qualitative infrared spectroscopy (IR) data analysis using characteristic absorption bands
• The principles of chromatography, including high performance liquid chromatography (HPLC) and the use of retention times and the construction and use of a calibration curve to determine the concentration of an organic compound in a solution (excluding features of instrumentation and operation)