Chapter 16 (Lecture #11)

Chapter 16 (Lecture #11) - Chapter 16 Aldehydes and Ketones...

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Chapter 16 Aldehydes and Ketones I Nucleophilic Additions to the Carbonyl Group General Features of the Carbonyl Group The general structure of the carbonyl group is C = O R R' : In a molecular orbital description , the carbon and oxygen atoms are hybridized sp 2 . A sigma bond is formed from overlap of sp 2 atomic orbitals, and the ! -bond is formed from overlap of p-orbitals. C O R R' : : The total bond strength for the C=O bond is ~176-179 kcal/mol. ! " "
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The carbonyl is a polar covalent bond because of the difference in electronegativities between C and O: C = O R R' !" ! + μ = 2.3-2.8 D Aldehydes and Ketones The general structures of these two closely related classes of organic compounds are: C O = R H C O R R' aldehydes ketones where the R and R' could also be aryl groups. Note: Aldehydes have at least one H .
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Nomenclature of Aldehydes Common names are derived from the common names of the corresponding carboxylic acids by dropping the "ic acid" and adding "aldehyde." CH 3 COOH CH 3 CH O = acet ic acid acet aldehyde COOH CH O benz oic acid benz aldehyde IUPAC or systematic names are based on the following rules where the aldehyde function is named as a suffix and has priority. (1) Select the longest continuous chain containing the -CHO as the parent . (2) Replace "e" in the alkane name with "al." (3) Number from the end where the carbonyl group is located and follow all the other rules for locating substituent groups. CH 3 CH 2 C CHO CH 3 CH 3 2,2-dimethylbutan al CH 3 CHCH 2 CH 2 CHO C 6 H 5 4-phenylpentan al
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Nomenclature of Ketones Common names are widely used for many of the simpler ketones. Acetone is the three carbon ketone: CH 3 CCH 3 O = The common names of other aliphatic ketones are based on the alkyl group names for R and R' followed by "ketone." CH 3 CH 2 CCH 3 O ethyl methyl ketone CH 3 CH 2 CH 2 CCH 3 O methyl propyl ketone
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Chapter 16 (Lecture #11) - Chapter 16 Aldehydes and Ketones...

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