A suitable protecting group for the hydroxyl group in the synthesis of a compound that also has an amine functional group is the tert-butyldimethylsilyl TBS group. The TBS group can be introduced using tert-butyldimethylsilyl chloride TBSCl and a base such as imidazole in the presence of an organic solvent like dichloromethane DCM .To remove the TBS protecting group under mild conditions, you can use a fluoride source such as tetra-n-butylammonium fluoride TBAF in an organic solvent like THF tetrahydrofuran . This reaction selectively cleaves the TBS group without affecting the amine functional group.To verify the presence of the hydroxyl group in the final product, you can use various analytical techniques such as:1. Infrared IR spectroscopy: The presence of the hydroxyl group can be confirmed by the appearance of a broad absorption band in the range of 3200-3600 cm-1, which is characteristic of O-H stretching vibrations.2. Nuclear Magnetic Resonance NMR spectroscopy: In 1H NMR, the hydroxyl proton typically appears as a broad singlet in the range of 1-5 ppm, depending on the chemical environment. In 13C NMR, the carbon atom directly attached to the hydroxyl group usually appears in the range of 60-90 ppm.3. Mass spectrometry MS : The presence of the hydroxyl group can be confirmed by the molecular ion peak and fragmentation pattern in the mass spectrum.4. Elemental analysis: The presence of the hydroxyl group can be confirmed by comparing the experimental and theoretical percentages of carbon, hydrogen, and other elements present in the compound.By using a combination of these analytical techniques, you can confirm the presence of the hydroxyl group in the final product.