Synthesis of Alkanes via FGI

Alkanes can be prepared via FGI starting with a variety of functional groups, including alkenes, alkynes, alkyl halides, alcohols, ketones, and aldehydes. In each case, the functional group is being replaced by simple C-H bonds, so these transformations will aU be described as reduction reactions. 

Introduction to Strategies for Organic Synthesis, First Edition. Laurie S. Starkey. 2012 John Wiley Sons, Inc. Published 2012 by John Wiley Sons, Inc. 

Alkane Synthesis from Alkyl Halides (Hydride/Grignard) 

Catalytic hydrogenation (H2, Pd) of an alkene or alkyne affords an alkane product. Aldehyde and ketone carbonyls can be completely reduced to a methylene group (CH2) by a variety of methods, including the acidic Clem-menson reduction (Zn/Hg, HCl) and the basic Wolff-Kishner reduction (NH2NH2, KOH). An alternate strategy is to convert the carbonyl to a thioac-etal that can then be reduced to an alkane with Raney nickel (Ni-H2). 

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