Mixed Method Analysis
Organic Analysis Worksheet
Note: The following questions take data from The Spectral Database for Organic Compounds (SDBS). As such, some of the puzzles are not ‘perfect’ because they are from real world data.
Identify the following compounds based on their test tube reactions and their spectra.
Compound 1
A compound would not react with acidified potassium dichromate, Tollens’ reagent, or sodium carbonate. It has the following spectra. What is the compound?
Structure
Compound 2
A compound reacted with potassium dichromate and reacts with Tollens’ reagent. It does not react with sodium carbonate or bromine water. Please note that the IR spectrum below is prepared using the KBr disc method, which can produce values with a wavenumber a little lower than other methods.
Structure
Compound 3
A compound reacted with sodium carbonate, producing bubbles; and reacted with acidified potassium dichromate. It did not react with Tollens’ reagent. It has the following spectra.
Structure
Compound 4
A compound decolourised bromine water and reacted with sodium carbonate. It did not react with acidified dichromate or Tollens’. It had the following spectra.
Structure
Compound 5
A compound was analysed and found to react with Tollens’ reagent but not acidified dichromate. It also reacted with bromine water, decolourising it. It had the following spectra.
Structure
(Check source for solution image – not provided in snippet)
Compound 6
The following molecule did not react with bromine water. It did not react with Fehlings but did react with LiAlH4. Please note that the source for this molecule was different and therefore there are visual differences between this molecule and the other molecules.
Structure
