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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 â¶Ä‰o´Ú â¶Ä‰â¶Ä‰H¹ó â¶Ä‰= â¶Ä‰3.87pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰H°ä±·â€‰â¶Ä‰= â¶Ä‰9.23pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰N±á3 â¶Ä‰= â¶Ä‰36pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰H2SO4 â¶Ä‰= â¶Ä‰-2.8pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰HCOOH  =  3.76pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰C±á4 â¶Ä‰= â¶Ä‰50pKa â¶Ä‰o´Ú â¶Ä‰â¶Ä‰H2°¿â€‰â¶Ä‰= â¶Ä‰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

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

(a)

(b)

(c)

(d)

(e)

(f)

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.

The following compound can become protonated on any of the three nitrogen atoms. One of these nitrogens is much more basic than the others, however.

  1. Draw the important resonance forms of the products of protonation on each of the three nitrogen atoms.
  2. Determine which nitrogen atom is the most basic.

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)

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