Alcohol, Phenol and Ether MCQ Questions & Answers in Organic Chemistry | Chemistry

\[\underset{\text{Ether}}{\mathop{{{\left( C{{H}_{3}}C{{H}_{2}} \right)}_{2}}}}\,O+\underset{\text{Acid anhydride}}{\mathop{{{\left( C{{H}_{3}}CO \right)}_{2}}O}}\,\xrightarrow{anhy.\,AlC{{l}_{3}}}\underset{\text{Ester}}{\mathop{C{{H}_{3}}COOC{{H}_{2}}C{{H}_{3}}}}\,\]

Phenol is less acidic than $$o$$ - nitrophenol as electron withdrawing $$\left( { - N{O_2}} \right)$$  group increases the acidity of phenols while electron donating groups $$\left( { - C{H_3}, - OC{H_3}} \right)$$    decrease the acidity of phenols. Phenols are more acidic than alcohols.

\[C{{H}_{3}}-C{{H}_{2}}-OH\xrightarrow[KMn{{O}_{4}}]{\left[ O \right]}\]       \[C{{H}_{3}}-CHO\left( \text{Oxidation} \right)\]

Alcohols have higher boiling points as compared to other organic compounds of similar molecular masses such as ethers. This is due to the presence of intermolecular hydrogen bonding in alcohols which is absent in ethers. Because of hydrogen bonding in alcohols, these exist as associated molecules rather than discrete molecules. Consequently, a large amount of energy is required to break these bonds and therefore, their boiling points are high.

Electron withdrawing group stabilises the benzene ring due to delocalisation of charge.
$$ - C{H_3}$$  and $$ - C{H_2}OH$$   are electron donating group and hence decrease the stability of benzene ring $$ - OC{H_3}$$  is weaker electron withdrawing group than $$ - COC{H_3}.$$   Hence $$ - COC{H_3}$$   group more stabilize the phenoxide ion at $$p$$ - position.

Electron withdrawing substituents like $$ - N{O_2},\,C{\text{l}}$$   increase the acidity of phenol while electron releasing substituents like $$ - C{H_3}, - OC{H_3}$$    decreases acidity.
hence the correct order of acidity will be

Further $$\left( { - I} \right)N{O_2} > \left( { - I} \right)Cl\,\,{\text{and}}\,\left( { + I} \right)C{H_3} > \left( { + I} \right)OC{H_3}$$

NOTE: This is Riemer - Tiemann reaction and the electrophile is dichlorocarbene.

\[{{C}_{6}}{{H}_{5}}C{{H}_{3}}+C{{l}_{2}}\left( exc. \right)\xrightarrow{\text{light,}\,\text{heat}}\]       \[{{C}_{6}}{{H}_{5}}CC{{l}_{3}}\xrightarrow{aq.\,NaOH}{{C}_{6}}{{H}_{5}}C{{\left( OH \right)}_{3}}\]       \[\xrightarrow{-{{H}_{2}}O}{{C}_{6}}{{H}_{5}}COOH\]