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Rank the following species in order of increasing basicity. Explain your reasons for ordering them as you do.

Short Answer

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A single structural formula sometimes cannot explain all the properties of a compound that is given. In such cases, the compound may be represented by two or more structural formulae which differ from each other only in the arrangement of electrons. None of this structural formula alone can explain all the observed properties of the compound. The compound is then said to show resonance. The various structures are known as resonating structures. The true structure of the molecule is not represented by any of the resonating structures but is considered to be a resonance hybrid of the various resonating structures.

Step by step solution

01

Resonance structures

A single structural formula sometimes cannot explain all the properties of a compound that is given. In such cases, the compound may be represented by two or more structural formulae which differ from each other only in the arrangement of electrons. None of this structural formula alone can explain all the observed properties of the compound. The compound is then said to show resonance. The various structures are known as resonating structures. The true structure of the molecule is not represented by any of the resonating structures but is considered to be a resonance hybrid of the various resonating structures.

02

Resonance effects on basicity

The basicity of common organic compounds is affected by resonance stabilization. Resonance delocalization of charges on a base helps in making the base more stabilized, and hence making it a weaker base and conjugate acid is strengthened.

03

Species in order of increasing basicity

Basicity mostly depends on electronegativity and delocalization of the negative charge of the base (anion). In anion (negatively charged ion) of sulfuric acid, the negative charge is delocalized on four highly electronegative oxygen atoms. So, will be the least basic. However, in amide the negative charge is not delocalized and it is present on the less electronegative nitrogen atom. So, is the most basic.

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Most popular questions from this chapter

N-Methylpyrrolidine has a boiling point of81οC, and piperidine has a boiling point of106οC.

  1. Explain the large difference (25οC) in boiling point for these two isomers.
  2. Tetrahydropyran has a boiling point of 88οC, and cyclopentanol has a boiling point of 141οC. These two isomers have a boiling point difference of 53οC.Explain why the two oxygen-containing isomers have a much larger boiling point difference than two amine isomers.
  3. N,N-Dimethylformamide has a boiling point of 150οC, and N-methylacetamide has a boiling point of 206οC, for a difference of 56οC.Explain why these two nitrogen-containing isomers have a much larger boiling point difference than the two amine isomers. Also explain why these two amides have higher boiling points than any of the other four compounds shown (two amines, an ether, and an alcohol).

The following compounds can all react as acids.

  1. For each compound, show its conjugate base. Show any resonance forms if applicable.
  2. Rank the conjugate bases in the order you would predict, from most stable to least stable.
  3. Rank the original compounds in order from strongest acid to weakest acid.

TheKa of phenylacetic acid is5.2 × 10-5, and thepKaof propionic acid is4.87.

(a)Calculate thepKaof phenylacetic acid and theKaof propionic acid.

(b) Which one of these is the stronger acid? Calculate how much stronger an acid it is.

(c) Predict whether the following equilibrium will favor the reactants or the products.

Compare the relative acidity of 1-molar aqueous solutions of the following acids.

Predict which member of each pair is more soluble in water. Explain your prediction.

(a)

(b)

(c)

(d)

(e)

(f)

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