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

Short Answer

Expert verified

Ka is known as the acid dissociation constant and its value indicates the relative strength of the acid. is defined as the negative logarithm (base ) of . Mathematically, . value of strong acids is usually zero or even negative while the value of weaker acids are greater than .

Step by step solution

01

Ka and pKa

Ka is known as the acid dissociation constant and its value indicates the relative strength of the acid. is defined as the negative logarithm (base ) of . Mathematically, . value of strong acids is usually zero or even negative while the value of weaker acids are greater than .

02

Species in order of increasing acidity

The strength of an acid or base is given by itsvalue. The smallervalue means stronger is the acid while the largervalue means stronger is the base.

pKa  of   HF  =  3.87pKa  of   HCN  =  9.23pKa  of   NH3  =  36pKa  of   H2SO4  =  -2.8pKa  of   HCOOH  =  3.76pKa  of   CH4  =  50pKa  of   H2O  =  15.7

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Most popular questions from this chapter

The pKa of ascorbic acid (vitamin C, page 9) is 4.17 , showing that it is lightly more acidic than acetic acid (CH3COOH,pKa =4.74) .

(a)Show four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.

(b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.

(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH ) group

Question: Circle the functional groups in the following structures. State to which class (or classes) of compounds the structure belongs.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

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).

Ozone has a dipole moment of 0.53 D. Carbon dioxide has a dipole moment of zero, even though C-O bonds are more polar than O-O bonds. Explain this apparent contradiction.

The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at different basic site. Draw the structure of the actual conjugate acid of acetamide, and explain (resonance) why protonation occurs where it does rather than on nitrogen. Calculate the pKa of this conjugate acid.

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