Alcohol Phenol And Ethers

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Payal Gupta

Contributor-Level 10

This is a short answer type question as classified in NCERT Exemplar

The electron withdrawing group (-NO2), withdraws electrons and disperses the negative charge. Therefore, -NO2 group stabilizes the phenoxide ion. Hence p-nitrophenol is more acidic than phenol.

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Payal Gupta

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The occurrence of intermolecular hydrogen bonds due to the H- bonds in alcohol compounds play a major role . With the increasing number of alkyl groups the molecular mass increases due to which the polar nature of these compounds get suppressed . Hence, the solubility factor of alcohols is indirectly proportional to the molecular mass.

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Payal Gupta

Contributor-Level 10

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The bond angle C—O—H in alcohols is less than tetrahedral angle because of the repulsion between the lone pairs present on the oxygen atom, which pushes the bond C—O—H closer. Therefore,   C—O—H bond angle in alcohols is slightly less than the tetrahedral angle.

In  ethers, the lone pairs on oxygen atoms are also present but the two bulky alkyl groups also have repulsive force which increases the C—O—C bond angle. Therefore,   the C—O—C bond angle in ether is slightly greater than tetrahedral angle .

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Payal Gupta

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Ethers are prepared by Williamson synthesis by the reaction of alkyl halide with the stadium alkoxide. But this is not possible in case of di-tert-butyl ether. In case of preparation of di-tert-butyl ether, tert-butyl halide must react with sodium tert-butoxide. Alkoxides are nucleophiles but they are strong bases as well, due to which elimination is favoured instead of substitution and leads to the formation of 2-methylprop-1-ene.

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Payal Gupta

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In phenol, the electron pairs on oxygen atom of -OH group are in conjugation (or resonance) with phenyl ring which decreases the polarity of the C-OH bond whereas in methanol the polarity of C-OH bond is more due to electron releasing group of -CH3.

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Payal Gupta

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Phenoxide ion is more reactive than phenol to electrophilic aromatic substitution reaction  due to the more in electron density of  phenoxide ion and hence, phenoxide ion easily undergoes the electrophilic substitution reaction than phenol by the weak CO2 electrophile.

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Payal Gupta

Contributor-Level 10

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The nitration of aromatic compounds occurs by using HSO4 and HNO3 which leads to the formation of  NO2+ (nitronium ion) electrophile.

Due to the formation of  NO2+ electrophile, we can say that nitration is an example of aromatic electrophilic substitution. The electron releasing group on the benzene ring increases the rate of nitration and vice-versa.

Phenol is more easily nitrated than benzene as the hydroxyl (-OH) group on the benzene ring is an electron releasing group which increases the electron density at the ortho and para position due to +R effect of -

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Payal Gupta

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Step 1: Addition of NaOH to obtain sodium phenoxide

Step 2: Sodium Phenoxide undergoes Kolbe's  reaction at high temperature and pressure in presence of carbon dioxide (CO2) gas.  The product is  further  hydrolysed  to obtain salicylic acid. 

Step 3: Acetylation of salicylic acid occur when it is treated with acetic anhydride

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Payal Gupta

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The reaction of alcohol with the conc. HCl and ZnCl2 (Lucas reagent) leads to the formation of a carbocation through SN1  mechanism. The more stable the carbocation, the faster the reaction will be.

Tertiary carbocation is the most stable due to hyperconjugation and inductive effect then is the secondary alcohol and the primary alcohol is the least stable.

Stability of carbocation:

Tertiary carbocation > Secondary carbocation  > Primary carbocation 

According to stability of carbocation, the reactivity order of the alcohol is:

Tertiary alcohol > Secondary alc

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Payal Gupta

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In  O? C? O, the dipole moment is zero, hence non-polar while in R—O—R the dipole moment is non-zero due to which it is polar.

The CO2 is a linear molecule and the dipole moment is equal and in the opposite direction due to which the dipole moment is zero. While in R—O—R, has bent structure and lone pair of electrons due to which the net dipole moment is nonzero and hence, it is a polar molecule.

The CO2 is a linear molecule and the dipole moment is equal and in the opposite direction due to which the dipole moment is zero. While in R—O—R, has bent

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