AQA Jan 2010 Paper 4 Q7

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areas outside the box will not be scanned for marking organic chemists use a variety of methods to identify unknown compounds when the molecular formula of a compound is known spectroscopic and other analytical techniques are used to distinguish between possible structural isomers use your knowledge of such techniques to identify the compounds described below use the three tables of spectral data on the data sheet where appropriate each part below concerns a different pair of structural isomers draw one possible structure for each of the compounds a to j described below a compounds a and b have the molecular formula c h o a has an absorption at cm in its infrared spectrum and has only one peak in its h n m r spectrum b has absorptions at cm and at cm in its infrared spectrum and does not show e z isomerism a b b compounds c and d have the molecular formula c h in their h n m r spectra c has three peaks and d has only one c d marks marks wmp jan chem areas outside the box will not be scanned for marking c compounds e and f are both esters with the molecular formula c h o in their h n m r spectra e has a quartet at ppm and f has a quartet at ppm e f d compounds g and h have the molecular formula c h o each exists as a pair of optical isomers and each has an absorption at about cm in its infrared spectrum g forms a silver mirror with tollens reagent but h does not g h marks e compounds i and j have the molecular formula c h n and both are secondary amines in their c n m r spectra i has two peaks and j has three i j marks marks turn over wmp jan chem

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