0112-Ch16 - Chapter 16 Aldehydes and Ketones Ch-16 The...

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Unformatted text preview: Chapter 16 Aldehydes and Ketones Ch-16 The Carbonyl Group Classes of compounds containing the carbonyl group , C=O. • aldehydes and ketones (Chapter 16) 1 Ch-16 C O R" R' C O R H (H) The Carbonyl Group Classes of compounds containing the carbonyl group , C=O (contd.). • Carboxylic acids (Chapter 17) 2 Ch-16 R C O OH RCOOH, RCO 2 H C C O C C O R C O Cl RCOCl (RCO) 2 O R C O C R O O R'COOR" R' C O OR" • Enolate anions (Chapter 19) • Acid halides, acid anhydrides, esters, amides (Chapter 18) The Carbonyl Group The carbonyl group (>C=O) as in aldehydes and ketones consists of • one σ (sigma) bond formed by the overlap of sp 2 hybrid orbitals and, in addition, • one π (pi) bond formed by the overlap of parallel 2 p orbitals between carbon and oxygen (see Chapter 1.7, Fig. 1.21). 3 Ch-16 The Carbonyl Group 4 Ch-16 Methanal (Formaldehyde): π bonding MO π * antibonding MO Energy Structure • The functional group of an aldehyde is a carbonyl group bonded to an H atom and a C atom: –CH=O (or –CHO). In methanal ( formaldehyde ) the carbonyl group is bonded to two H atoms: H 2 C=O. • The functional group of a ketone is a carbonyl group bonded to two carbon atoms. 5 Ch-16 Nomenclature: Aldehydes • The parent chain is the longest chain that contains the carbonyl group. • For an aldehyde , change the alkan e suffix from -e to -al . • For an unsaturated aldehyde , change the alk an e infix from - an- to -en- ; the location of the suffix determines the numbering pattern. 6 Ch-16 IUPAC names: Nomenclature: Aldehydes • For a cyclic molecule , in which –CH=O (–CHO) is bonded to the ring, add the suffix -carbaldehyde . 7 Ch-16 • The IUPAC naming retains some common names: formaldehyde (H 2 CO), acetaldehyde (CH 3 CHO), benzaldehyde (PhCHO), and cinnamaldehyde . IUPAC names (contd.): Nomenclature: Ketones • The parent alkane is the longest chain that contains the carbonyl group. • Indicate the ketone by changing the suffix -e of the alkane to -one . • Number the chain to give C=O the smaller number. • The IUPAC retains the common names acetone , acetophenone , and benzophenone . 8 Ch-16 IUPAC names: Order of Precedence For compounds that contain more than one functional group indicated by a suffix. 9 Ch-16 Functional Group SufFx if Higher Priority PreFx if Lower Priority Example (when the functional group has lower priority) Carboxyl-oic acid – O CO 2 H 2-ethyl-5- oxo pentan oic acid Aldehyde-al oxo- Ketone-one oxo- O O 4- oxo hexan al Alcohol-ol hydroxy- 4- hydroxy hexan al O OH Amine-amine amino- 3- amino propan-1- ol H 2 N OH Sulfhydryl-thiol mercapto- 3- mercapto propan-1- ol HS OH Increasing Precedence Common Names • For an aldehyde , the common name is derived from the common name of the corresponding carboxylic acid....
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This note was uploaded on 02/15/2012 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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0112-Ch16 - Chapter 16 Aldehydes and Ketones Ch-16 The...

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