Example Alkane TM

Synthesize the following TM, using readily available starting materials and reagents. The synthesis must involve the formation of a new C-C bond. 

There are several possible syntheses of this compound. One possible FGI on the branched alkane TM leads to an alkene. This alkene can be prepared in a number of ways, including by dehydration of an alcohol or with a 

Wittig reaction. Another option is to consider disconnecting at the aromatic ring and utilizing a Friedel-Crafts reaction. Since the alkyl group would require an unstable 1° carbocation, synthesis via Friedel-Crafts alkylation is impossible. Instead, an FGI that installs a carbonyl at the benzylic position gives an aromatic ketone that can undergo a Friedel-Crafts acylation disconnection. 

Three possible syntheses are presented for the given TM, each of which forms a new C-C bond as required via Grignard, Wittig, or Friedel-Crafts reactions. The acid chloride required for the Friedel-Crafts acylation can be prepared from the corresponding carboxylic acid (the synthesis of compounds containing these functional groups are discussed in Chapters 3.10 and 3.11)- 

Aldehyde and ketone carbonyls can be created via FGIs, and compounds already containing a carbonyl can be functionalized by reaction with either the electrophilic carbonyl carbon (e.g., acyl substitution reactions) or the nucleophilic alpha carbon. Both strategies can be used to give aldehyde and ketone products. 

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