BIOL373L Lecture Notes - Lecture 18: Trigonal Planar Molecular Geometry, Aldehyde, Ketone
12 Mar 2021
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Al pictures reproduced with permission from top hat. They occur widely in nature as intermediates in metabolism and biosynthesis. Aldehydes and ketones are particularly prevalent in carbohydrates and nucleic acids. The carbon of the carbonyl is sp2 hybridized, giving the carbonyl a trigonal planar geometry with bond angles of 120 . When compared to a c=c bond, the c=o bond is stronger, shorter, and polarized. Aldehydes and ketones can react as a nucleophile or electrophile. Ozone (o3) adds to alkenes and cleaves them, resulting in aldehydes and/or ketones, depending on the substitution of the alkene. (textbook 22. 3. 1) You are not responsible for the mechanisms of these reactions. Alcohols can be oxidized to form aldehydes and ketones. Primary alcohols are oxidized to aldehydes using specialized reagents (typically dess-martin periodinane, dmp, or pyridinium chlorochromate, pcc or swern oxidation). Ketones are prepared from secondary alcohols using a variety of oxidizing agents, while tertiary alcohols cannot be oxidized.
