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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

What products would you expect from oxidation of the following compounds with CrO3 in aqueous acid? With the Dess-Martin periodinane?

  1. 1-Hexanol
  2. 2-Hexanol
  3. Hexanal

What products would you expect to obtain from reaction of 1-methylcyclohexanol with the following reagents?

(a) HBr (b) NaH (c) H2SO4 (d) Na2Cr2O7

A compound of unknown structure gave the following spectroscopic data:

Mass spectrum:M+=88.1

IR: 3600 cm-1

1HNMR: 1.4δ (2H, quartet, J=7Hz); 1.2δ (6H, singlet); 1.0δ (1H, singlet); 0.9δ (3H, triplet, J=7Hz)

13CNMR: 74, 35, 27, 25δ

(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.

(b) How many protons (H) does the compound contain?

(c) What functional group(s) does the compound contain?

(d) How many carbons does the compound contain?

(e) What is the molecular formula of the compound?

(f) What is the structure of the compound?

(g) Assign peaks in the molecule’s NMR spectrum corresponding to specific protons.

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

Question: Give IUPAC names for the following compounds:
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