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CHMB42H3 (16)
Chapter 17

CHMB42 Chapter 17

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University of Toronto Scarborough
Wanda/ Lana

Chapter 17 Carbonyl Compounds IINomenclature of Aldehydes and KetonesThe systematic name of an aldehyde is obtained by replacing the final e on the name of the parent hydrocarbon with al ethanal 2bromopropanal or methanalTerminal e is removed only to avoid two successive vowels hexanedial e isnt removedIf a compound has two functional groups the one with the lower priority is indicated by a prefix and the one with the higher priority by a suffixThe systematic name of a ketone is obtained by replacing the final e on the end of the name of the parent hydrocarbon with oneThe chain is numbered in the direction that gives the carbonyl carbon the smallest number 3hexanone 6methyl2heptanone or acetoneIf the ketone has a second functional group of higher naming priority the ketone oxygen is indicated by the prefix oxoIncreasing Priority Alkyl HalideEtherAlkaneAlkyneAlkeneAmineAlcoholKetoneAldehydeNitrileAmideEsterCarboxilic AcidRelative Reactivities of Carbonyl CompoundsSince a hydrogen is electron withdrawing compared to an alkyl group an aldehyde is more reactive than a ketone toward nucleophilic attack formaldehydealdehydeketoneSteric factors also contribute to the greater reactivity of an aldehyde making the carbonyl carbon of an aldehyde more accessible to the nucleophile than is the carbonyl carbonRelative Reactivities of Carbonyl Compounds Acyl HalideAcid AnhydrideAldehydeKetoneEsterCarboxylic AcidAmideCarboxylate IonAldehydes and ketones are not as reactive as carbonyl compounds in which Y is a very weak base but more reactive in which Y is a relatively strong baseHow Aldehydes and Ketones ReactAldehydes and ketones do not undergo acyl substitution reactionsNucleophilic Addition Reaction irreversible reaction when a nucleophile adds to the carbonyl group of an aldehyde or a ketone and nothing is expelled due to nucleophile being a strong baseIf the nucleophile is a relatively weak base the product of the reaction will again be the tetrahedral compound but reversibleNucleophilic AdditionElimination Reaction if the attacking atom of the nucleophile has a lone pair and there is sufficient acid to protonate the OH group of the tetrahedral compound water can be eliminated from the addition product reversibleReactions of Carbonyl Compounds with Grignard ReagentsAddition of a Grignard reagent to carbonyl compounds leads to the formation of a new CC bond with the Grignard reagent acting as a nucleophile thats a strong baseAldehydes and ketones undergo nucleophilic addition reactions with Grignard reagentsWhen a Grignard reagent RMgX reacts with formaldehyde the addition product is a primary alcoholWhen a Grignard reagent RMgX reacts with an aldehyde other than formaldehyde the addition product is a secondary alcohol
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