Devise the most efficient synthesis for the carboxylic acid below using a starti

Question

Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the sturting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol(4) with conc. HCl(Q then treat the product with KOH in alcohol(h). CH3 Starting materials Br Br HsC Reagents a Mg dry ether e Aqueous H2SO4 at reflux b1.co2 2. acidic workup f Conc. HCI or HCI (gas) j Na2 CrO4aqeous H2SO c NaCN THF or DMF k 1. BHyTHF 2. H20aq. NaOH d NaCN/dil. aqueous H2SO4 h KOH/ akcoho

Explanation / Answer

1 by using reagent a followed by b

2 by using reagent d

3 by using reagent i

4 by using reagent f followed by h

5 by using reagent j

6.by using reagent i

7. by using reagent l

8.by using reagent k followed by i

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