By Dorothy Bartlett
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Additional info for Advanced Practical Organic Chemistry
In step-2 the alkene reacts with A to form a π complex, B, which undergoes rearrangement (step-3) of an H to one of the C’s of the double bond, the other C forming a σ bond to the Rh (C). 44 Advanced Practical Organic Chemistry In the last step, a second H is transferred to the other C, and the alkane is lost with simultaneous regeneration of the metal catalyst— The reagents for carrying out the following transformations, indicated : Advanced Practical Organic Chemistry 45 (a) OsO4 (b) OsO4 (c) SeO2 (d) SeO2 (e) SeO2 (f) OsO4 Transformation Regents (1) ( 2 (1) (CH3)2CuLi (Lithium dimethyl cuprate).
The main chain must include the functional group and the numbering is such that the functional group is at the lowest number possible. , 2,2-dimethyl-3-pentanone and not 4,4-dimethyl-3-pentanone): Fig. (a) 3-Methyl-2-butanone; (b) 2,2-dimelhyl-3-pentanone; (c) 4-ethyl-3-methyl-2-hexanone; (d) 3-methylcyclohexanone. 3-Methyl-2-butanone can in fact be simplified to 3-methylbutanone because there is only one possible place for the ketone functional group in this molecule. In case the c a r b o n y l C = O group is at the end of the chain; it would be an aldehyde and not a ketone.
Umpolung : The reversal of polarity of the carbonyl carbon atom is termed umpolung (German : for polarity reversal). , electrophilic and therefore it reacts with nucleophiles. When the aldehyde is converted to a dithiane by reaction with 1,3-propanedithiol and reacted with butyl lithium the same carbon now becomes negatively charged to react with electrophiles. This reversed polarity of the carbonyl carbon is termed umpolung which increases the versatility of the carbonyl group in synthesis. The sulphur atoms stabilize carbanions because sulphur has the capacity to utilize 3d orbitals for bonding and to occur in valence states higher than 2.
Advanced Practical Organic Chemistry by Dorothy Bartlett