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Design a strategy to protect the alcohol functional group in a molecule containing both a primary amine and a carboxylic acid group, to prevent unwanted reactions during organic synthesis.

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To protect the alcohol functional group in a molecule containing both a primary amine and a carboxylic acid group, we can use a selective protecting group that will only react with the alcohol and not interfere with the other functional groups. A suitable protecting group for this purpose is the tert-butyldimethylsilyl  TBS  group. The TBS group can be introduced using tert-butyldimethylsilyl chloride  TBSCl  and a suitable base, such as imidazole.Here's the step-by-step strategy:1. Protection of the alcohol group:React the starting molecule with TBSCl and imidazole in an anhydrous solvent, such as dichloromethane  DCM , at room temperature. The reaction will selectively protect the alcohol group as the tert-butyldimethylsilyl ether, leaving the primary amine and carboxylic acid groups untouched.2. Perform the desired organic synthesis:With the alcohol group protected, you can now carry out the desired organic synthesis reactions without worrying about the alcohol group participating in any unwanted reactions.3. Deprotection of the alcohol group:Once the desired organic synthesis is complete, the TBS protecting group can be removed to regenerate the alcohol group. This can be achieved by treating the molecule with a mild acid, such as tetrabutylammonium fluoride  TBAF  in THF, or a buffered solution of hydrofluoric acid  HF  in pyridine.In summary, the use of a TBS protecting group allows for the selective protection of the alcohol functional group in the presence of primary amine and carboxylic acid groups, enabling the desired organic synthesis to proceed without interference from the alcohol group.

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