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Chapter 19

chm247 all about Chapter 19.pdf

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Cecilia Kutas

July 1819 2012 CHM247H1Aldehydes and KetonesOCHEMISTRY OF THE CARBONYL GROUPVery important to biochemistry C THE OCCURRENCE OF THE CARBONYL GROUP IN COMPOUNDS IN NATURESugars o All sugars are aldehydes or ketones with hydroxyl OH groups no Remember a molecule with n chirality centres can have up to 2 stereoisomers but it may not necessarily have this many CHOOHHglucose Fischer HHOProjections HCHOHC2OHHHOHHHOOHHHOCHOHOCHOH2Ho Daldohexoses aldose sugarsaldehydecontaining sugars hexose6carbon sugar This stereocenter doesnt change Note that the carbonyl group is at the top of the Fischer projectionby convention the highest priority group is written at the topAll the stereocenters in Fischer projections are eclipsed CHM247H1 Other aldehydes exaromatic natural products from plantso R and Scarvone are only different in stereochemistry at the stereocenter of the compound yet our olfactory receptors interpret the two enantiomers VERY differentlyCO CHEMISTRY IS CENTRAL TO BIOCHEMISTRY discussed in chapters 1923 of McMGeneral principles of reactivity recognize the patterns o Nucleophiles attack electrophiles obonds are more easily broken thanbonds o Good leaving groups leave taking their electrons with them ieheterolytic bond cleavage wherein the leaving group takes the electron pair that previously bonded it to the reaction centreTYPES OF CARBONYL COMPOUNDS Whatever is connected to the CO changes the functional groups reactivity 1 Only H or C attached to a COo Aldehydes and ketones can undergo nucleophilic addition 2 An electronegative atom attached to CO usually a good leaving groupo Acid halides will undergo nucleophilic substitution reactions instead of addition reactionsLOOKING AT ALDEHYDES AND KETONESNomenclature use al or one as suffix if naming as aldehyde or ketoneo Aldehyde is the higher priority as it is always at C1 when a carbonyl CO group is a substituent it is named oxo
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