Chapter 17 - Chapter 17 Aldehydes and Ketones: Nucleophilic...

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Chem 212 B. R. Kaafarani 1 Chapter 17 Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group C O R Acyl group
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Chem 212 B. R. Kaafarani 2 H O O H O HCCHCH O B a s et h en a m eo n the chain that contains the carbonyl group and replace the -e ending of the hydrocarbon by -al . 17.1. IUPAC Nomenclature of Aldehydes 4,4-dimethylpent an al 5-hex en al 2-phenylprop ane dial (keep the -e ending before -dial )
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Chem 212 B. R. Kaafarani 3 When formyl group named as a substituent on a ring -carbaldehyde The ring name is followed by the suffix C H O IUPAC Nomenclature of Aldehydes O H Cyclopentanecarbaldehyde Make sure to check out formaldehyde, acetaldehyde, benzaldehyde (common names!).
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Chem 212 B. R. Kaafarani 4 CH 3 CH 2 CCH 2 CH 2 CH 3 O CH 3 CHCH 2 CCH 3 O CH 3 H 3 C O Base the name on the chain that contains the carbonyl group and replace -e by -one . Number the chain in the direction that gives the lowest number to the carbonyl carbon. Substitutive IUPAC Nomenclature of Ketones 3- hexan one 4-methyl -2- pentan one 4-methylcyclohexan one The prefix oxo - is used if other functional groups are present and the doubly bonded oxygen is labeled as a substituent on a parent chain.
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Chem 212 B. R. Kaafarani 5 CH 3 CH 2 C CH 2 CH 2 CH 3 O O PhCH 2 C CH 2 CH 3 CH CH 2 O H 2 C CHC List the groups attached to the carbonyl separately in alphabetical order, and add the word ketone . Functional Class IUPAC Nomenclature of Ketones Ethyl propyl ketone Benzyl ethyl ketone Divinyl ketone Check out the common names: acetone, acetophenone, benzophenone.
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Chem 212 B. R. Kaafarani 6 Functional Groups – Hierarchy and Classification Subordinate groups are azides (azido); halides (halo); and nitro (nitro). These groups have no established priority order. Priority high low
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Chem 212 B. R. Kaafarani 7 - Planar - Bond angles: close to 120° - C=O bond distance: 122 pm Structure of Formaldehyde 17.2. Structure and Bonding: The Carbonyl Group O H H
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Chem 212 B. R. Kaafarani 8 1-butene Propanal O dipole moment = 0.3 D dipole moment = 2.5 D very polar double bond The Carbonyl Group
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Chem 212 B. R. Kaafarani 9 C O •• C O + •• Resonance Description of Carbonyl Group Nucleophiles attack carbon. Oxygen attacks electrophiles.
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Chem 212 B. R. Kaafarani 10 2475 kJ/mol 2442 kJ/mol Heat of combustion O O H Carbonyl group of a ketone is more stable than that of an aldehyde Alkyl groups stabilize carbonyl groups the same way they stabilize carbon-carbon double bonds, carbocations, and free radicals.
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Chem 212 B. R. Kaafarani 11 Heats of combustion of C 4 H 8 isomeric alkenes CH 3 CH 2 CH=CH 2 2717 kJ/mol cis -CH 3 CH=CHCH 3 2710 kJ/mol trans -CH 3 CH=CHCH 3 2707 kJ/mol (CH 3 ) 2 C=CH 2 2700 kJ/mol 2475 kJ/mol 2442 kJ/mol O O H Range of stabilization is greater for aldehydes and ketones than for alkenes
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Chem 212 B. R. Kaafarani 12 Half-filled sp 2 orbitals of carbon and oxygen overlap to form a -bond.
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This note was uploaded on 01/06/2012 for the course CHEM 212 taught by Professor Bilalkaafarani during the Fall '10 term at American University of Beirut.

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Chapter 17 - Chapter 17 Aldehydes and Ketones: Nucleophilic...

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