Each —OH group of the following compound has a different acidity. What products are formed when the compound is treated with various amounts of NaH and then treated with a methylating agent? Explain.





(i) reaction using 1 eq. of NaH followed by 1 eq of CH₃I with heat
(ii) reaction using 2 eq. of NaH followed by 2 eq of CH₃I with heat
(iii) reaction using 3 eq. of NaH followed by 3 eq of CH₃I with heat

• A. The reactions involve the deprotonation and methylation of the hydroxyl groups. The first NaH equivalent will remove the most acidic proton from the phenolic group, the second NaH equivalent will remove the carboxylic proton, and the third equivalent will remove the proton from the primary alcohol.
  
• B. The reactions involve the deprotonation and methylation of the hydroxyl groups. The first NaH equivalent will remove the most acidic proton from the phenolic group, the second NaH equivalent will remove the primary alcohol proton, and the third equivalent will remove the proton from the carboxylic group.
  
• C. The reactions involve the deprotonation and methylation of the hydroxyl groups. The first NaH equivalent will remove the most acidic proton from the carboxylic group, the second NaH equivalent will remove the phenolic proton, and the third equivalent will remove the proton from the primary alcohol.
  
• D. The reactions involve the deprotonation and methylation of the hydroxyl groups. The first NaH equivalent will remove the most acidic proton from the primary alcohol, the second NaH equivalent will remove the phenolic proton, and the third equivalent will remove the proton from the carboxylic group.
  

Answer: (C)