Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the correct decreasing order of acidic character for the following compounds: CH ₃ C CH , MeOH , Me ₂ CHOH , Me ₃ COH , and H ₂ O .
Options
- AMeOH > Me ₂ CHOH > Me ₃ COH > H ₂ O > CH ₃ C CH
- BMeOH > H ₂ O > Me ₂ CHOH > Me ₃ COH > CH ₃ C CH
- CCH ₃ C CH > Me ₃ COH > Me ₂ CHOH > MeOH > H ₂ O
- DMe ₃ COH > Me ₂ CHOH > MeOH > H ₂ O > CH ₃ C CH
Correct answer
B. MeOH > H ₂ O > Me ₂ CHOH > Me ₃ COH > CH ₃ C CH
Step-by-step solution
The acidic strength depends on the stability of the conjugate base formed after the removal of a proton. The conjugate bases are CH ₃ C C ⁻ , CH ₃ O ⁻ , ( CH ₃)₂ CHO ⁻ , ( CH ₃)₃ CO ⁻ , and OH ⁻ . Oxygen is more electronegative than sp-hybridized carbon, so the negative charge is more stable on the oxygen atom. Therefore, water and alcohols are more acidic than propyne ( CH ₃ C CH ). Among water and alcohols, the electron-donating +I effect of alkyl groups destabilizes the alkoxide ion. The +I effect increases in t