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Chapter 17: Q.16. (page 641)

Question: Rank the following compounds in the order of increasing acidity.

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01

Conjugate Acid

A conjugate acid-base pair in which the two substances differ only by the presence of a proton is known as acids and bases according to the Lowry-Bronsted concept.

By adding a proton to a base, a conjugate acid is formed, and by the removal of a proton from an acid, a conjugate base is formed.

02

Conjugate acid-base relationship

The strength of an acid or base and the strength of its conjugate base or conjugate acid are interrelated. The relation is that as the acid strength increases, the conjugate base becomes weaker. The acid is weaker, the strength of the conjugate base is strong.

03

Ranking the compound in the increasing order of acidity

The compounds with the most stable conjugate base are the most acidic.

  • For the first one, there is no delocalization due to resonance; so, it has the most unstable base and, hence, least acidic acid.
  • For the second one, there are two resonance structures; so, the acid has an intermediate acidity.
  • For the third one, an aromatic conjugate base that is most stable is present; so, the acid will be most acidic.

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Most popular questions from this chapter

Question: You have a sample of a compound of molecular formula C11H15NO2, which has a benzene ring substituted by two groups, (CH3)2N-and -CO2CH2CH3 , and exhibits the given C13 NMR. What disubstituted benzene isomer corresponds to these C13 data?

Question: What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150–2850 role="math" localid="1648710122642" cm-1and gives the following 1 H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm

Question: Methotrexate, a drug that inhibits the metabolism of folic acid, is used in the treatment of a variety of cancers and autoimmune disorders such as rheumatoid arthritis. (a) Give the hybridization of each N atom in methotrexate. (b) In what type of orbital does the lone pair of each N reside? (c) Explain why the bicyclic ring system that contains four N atoms is aromatic.

Question: Zolpidem (trade name Ambien) promotes the rapid onset of sleep, making it a widely prescribed drug for treating insomnia.

a. In what type of orbital does the lone pair on each N atom in the heterocycle reside?

b. Explain why the bicyclic ring system that contains both N atoms is aromatic.

c. Draw all reasonable resonance structures for the bicyclic ring system.

Question: Which of the diethylbenzene isomers (ortho, meta, or para) corresponds to each set of C13NMR spectral data?

[A] C13NMR signals: 16, 29, 125, 127.5, 128.4, and 144 ppm

[B] C13 NMR signals: 15, 26, 126, 128, and 142 ppm

[C] C13NMR signals: 16, 29, 128, and 141 ppm
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