Textbook Notes (363,264)
Canada (158,281)
Chemistry (251)
CHMB42H3 (16)
Chapter 17

CHAPTER 17 - Textbook Notes.docx

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University of Toronto Scarborough
Lana Mikhaylichenko

CHAPTER 17 CARBONYL CAOMPOUNDS I REACTIONS OF CARBOXYLIC ACIDS AND CARBOXYLIC ACID DERIVATIVES Carbonyl Groupa carbon double bonded to an oxygen Carbonyl Compounda compound that contains a carbonyl group An acyl group consists of carbonyl group attached to an alkyl group R or to an aryl group Ar The group or atom attached to the acyl group strongly affects the reactivity of the carbonyl compound Class I carbonyl compounds are those in which the acyl group is attached to a group or atom that can be replaced by another group Carboxylic acids acyl halides acid anhydrides esters and amides belong to this class All these compounds contain a group OH Cl OR NH NHR NR that can be replaced by a nucleophile22Acyl halides acid anhydrides esters and amines are called carboxylic acid derivatives because they differ from a carboxylic acid only in the nature of the group or atom that has replaced the OH group of the carboxylic acid Class II carbonyl compounds are those in which the acyl group is attached to a group that cannot be readily replaced by another group Aldehydes and ketones belong to this class The H bonded to the acyl group of an aldehydes and the R group bonded to the acyl group of a ketone cannot be readily replaced by a nucleophile Weak bases are good leaving groups and strong bases are poor leaving groups because weak bases do not share their electrons as well as strong bases do The lower the pK the stronger the acid and the weaker its conjugate basea 171 The Nomenclature of Carboxylic Acids and Carboxylic Acid DerivativesNaming Carboxylic Acids The functional group of a carboxylic acid is called a carboxyl group In systematic IUPAC nomenclature a carboxylic acid is named by replacing the terminal e of the alkane name with oic acid For example the onecarbon alkane is methane so the onecarbon carboxylic acid is methanoic acid In systematic nomenclature the position of a substituent is designated by a number The carbonyl carbon is always the C1 carbon The carbon adjacent to the carbonyl carbon is the carbon the carbon adjacent to the carbon is the carbon and so on
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