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

The electron withdrawing group $$\left( { - N{O_2}} \right)$$   increases the acidity of phenols and the electron donating group $$\left( { - OC{H_3}} \right)$$   decreases the acidity of phenols. The effect at $$p$$ - position is greater than at $$m$$ - position.

$$KMn{O_4}$$  will oxidise initially formed aldehydes to carboxylic acids.

Reimer-Tiemann reaction When phenol is treated with chloroform and $$NaOH,$$  salicylaldehyde is obtained.

Phenols are much more acidic than alcohols, due to the stabilisation of phenoxide ion by resonance

Phenoxide ion is stabilised due to following resonating structures :

Compound $$B$$ is a Sec. alcohol since it gives blue colour in Victor-Meyer test and Sec alcohol are obtained by the action of $$C{H_3}MgI$$  on an aldehyde other than formaldehyde.
So $$A$$ is Acetaldehyde and $$B$$ is Isopropyl Alcohol.

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\[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}OH\xrightarrow[\Delta ]{{{H}^{+}}}\]       \[\underset{\text{But-l-ene}}{\mathop{C{{H}_{3}}C{{H}_{2}}CH=C{{H}_{2}}}}\,\]

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Thinking Process This problem is based on the resonance stabilisation.
In anisol, methyl phenyl oxonium ion is formed by protonation of ether. The bond between $$O - C{H_3}$$  is weaker than the bond between $$O - {C_6}{H_5},$$   because the carbon of phenyl group is $$s{p^2}$$ - hybridised and there is a partial double bond character. Thus, the reaction yields phenol and alkyl halide.

Reagents used in the various steps indicate that the compound $$Z$$  has an alcoholic group. This set of reactions is possible only when $$Z$$  is $$C{H_3}CHOHC{H_3}.$$

In options A and C, $$Y$$  cannot be converted back into D by the given series of reactions.