Ch 16_1

Ch 16_1 - Nomenclature Compounds with C=O Group IUPAC...

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Unformatted text preview: Nomenclature Compounds with C=O Group IUPAC names: the parent chain is the longest chain that contains the C=O functional group for an aldehyde, change the suffix from -e to -al for an unsaturated aldehyde, change the infix from -an- to -en- ; the location of the suffix determines the numbering pattern for a cyclic molecule in which -CHO is bonded to the ring, add the suffix - carbaldehyde 1 Nomenclature: Aldehydes the common names benzaldehyde and cinnamaldehyde, as well formaldehyde and acetaldehyde are IUPAC-accepted names H O 3-Methylbutanal 2-Propenal (Acrolein) (2 E )-3,7-Dimethyl-2,6-octadienal (Geranial) 1 2 3 4 5 6 7 8 H O H O CHO HO CHO Cyclopentane- carbaldehyde trans-4-Hydroxycyclo- hexanecarbaldehyde 1 4 CHO C 6 H 5 CHO trans-3-Phenyl-2-propenal (Cinnamaldehyde) Benzaldehyde 2 Nomenclature: Ketones IUPAC names the parent alkane is the longest chain that contains the carbonyl group indicate the ketone by changing the suffix -e to - one number the chain to give C=O the smaller number the common names acetone, acetophenone, and benzophenone are IUPAC-accepted names Propanone (Acetone) Benzophenone 1-Phenyl-1-pentanone Acetophenone O O O O 3 Common Names for an aldehyde, the common name is derived from the common name of the corresponding carboxylic acid for a ketone, name the two alkyl or aryl groups bonded to the carbonyl carbon and add the word ketone HCH O HCOH O CH 3 CH O CH 3 COH O Formaldehyde Formic acid Acetaldehyde Acetic acid Ethyl isopropyl ketone Diethyl ketone Dicyclohexyl ketone O O O 4 Order of Precedence For compounds that contain more than one functional group indicated by a suffix H COOH O COOH O COOH HO OH HS COOH NH 2 Functional Group Carboxyl-oic acid Aldehyde-al oxo- Ketone-one oxo- Alcohol-ol hydroxy- Amino-amine amino- 3- Oxo propanoic acid 3- Oxo butanoic a cid 4- Hydroxy butanoic acid 3- Amino butanoic acid Example when the functional group has a lower priority Sulfhydryl-thiol mercapto 2- M ercapto ethanol Suffix if higher priority Prefix if lower priority 5 Physical Properties Oxygen is more electronegative than carbon (3.5 vs 2.5) and, therefore, a C=O group is polar aldehydes and ketones are polar compounds and interact in the pure state by dipole-dipole interaction they have higher boiling points and are more soluble in water than nonpolar compounds of comparable molecular weight 6 Common C=O Reactions 1. Addition of a nucleophile to form a tetrahedral carbonyl addition compound 2. Acidic activation of carbonyl to form resonance-stabilized cation which is even more reactive with nucleophiles + C R R O C Nu O - R R Nu - Tetrahedral carbonyl addition compound B - C O R R H-Nu H-B C O R R H B - C O R R H C Nu O-H R R C O R R H H-B + fast + + + + slow + + + 7 Stereochemistry often the tetrahedral product of addition to a carbonyl is a new chiral center if none of the starting materials is chiral and the...
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Ch 16_1 - Nomenclature Compounds with C=O Group IUPAC...

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