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Chapter 17: Q17-59E (page 567)

Rank the following substituted phenol in the increasing order of acidity, and explain your answer:

Short Answer

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The answer is

Step by step solution

01

Acidity in phenols

The acidity of alcohols can be defined as the tendency of alcohols to donate the protons and forms a stable oxide anion. The acidity of alcohols depends on the stability of the oxide anion formed.

02

Explanation

The increasing order of acidity is shown below.

Electron-withdrawing groups on phenol can stabilise the anions formed after losing the protons(that is phenoxide ion) and hence become more acidic. The electron-donating groups, in turn, decrease acidity.

-CN group can stabilise the phenoxide ion by mesomeric effect.

-F is an electronegative atom.

-OCH3is an electron donating group that will decrease the acidity of the phenol.

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Most popular questions from this chapter

Propose structures for alcohols that have the following H1 NMR spectra:

(a) C5H12O

(b) C8H10O

Draw structures corresponding to the following IUPAC names:

  1. (Z)-2-Ethyl-2-buten-1-ol
  2. 3-Cyclohexen-1-ol
  3. trans-3-Chlorocycloheptanol
  4. 1,4-Pentanediol
  5. 2,6-Dimethylphenol
  6. o-(2-Hydroxyethyl)phenol

Question: What carbonyl compounds give the following alcohols on reduction with ? Show all possibilities.

(a)

(b)

(c)

(d)CH32CHCH2OH

When the H1NMR spectrum of an alcohol is run in dimethyl sulfoxide (DMSO) solvent rather than in chloroform, exchange of the O-H proton is slow and spin-spin splitting is seen between the O-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols?

  1. 2-Methyl-2-propanol
  2. Cyclohexanol
  3. Ethanol
  4. 2-Propanol
  5. Cholesterol
  6. 1-Methylcyclohexanol

What product (s) would you expect from dehydration of the following alcohols with POCl3in pyridine? Indicate the major product in each case.

(a)

(b)

(C)

(d)

(e)
See all solutions

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