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.
162.
Which of the following reagents cannot be used to oxidise primary alcohols to aldehydes?
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 :
165.
An organic compound $$A$$ reacts with methyl magnesium iodide to form an addition product which on hydrolysis forms the compound $$B.$$ Compound $$B$$ gives blue colour salt in Victor Meyer’s test. The compounds $$A$$ and $$B$$ are respectively
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.
166.
\[{{\left( C{{H}_{3}} \right)}_{3}}C-C{{H}_{2}}OH\xrightarrow[{{170}^{\circ }}C]{\text{Conc}.\,{{H}_{2}}S{{O}_{4}}}X\]
In the reaction, $$X$$ is
A
$${\left( {C{H_3}} \right)_2}C = CHC{H_3}$$
B
$$C{H_3}C \equiv CH$$
C
$${\left( {C{H_3}} \right)_2}CHC{H_2}C{H_3}$$
D
\[C{{H}_{3}}-C{{H}_{2}}\underset{\begin{smallmatrix}
|\,\, \\
\,\,C{{H}_{3}}
\end{smallmatrix}}{\mathop{-C=}}\,C{{H}_{2}}\]
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.
170.
What is $$Z$$ in the following sequence of reactions ?
\[Z\xrightarrow{PC{{l}_{5}}}X\xrightarrow{Alc.\,KOH}Y\] \[\xrightarrow[\left( \text{ii} \right)\,{{H}_{2}}O;\,\text{boil}]{\left( \text{i} \right)\,Conc.\,{{H}_{2}}S{{O}_{4}}}Z\]
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.