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Chapter 2: 37P (page 139)

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

Draw a Lewis structure, and classify each of the following compounds. The possible classification are as follows:

alcohol, ketone, carboxylic acid, ether, aldehyde and alkene.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

Classify the following hydrocarbons, and draw a lewis structure for each one. A compound may fit into more than one of the following classifications:

Alkane, alkene, alkyne, cycloalkane, cycloalkene, cycloalkyne, aromatic hydrocarbon.

  1. (CH3CH2)2CHCH(CH3)2
  2. CH3CHCHCH2CH3
  3. CH3CCCH2CH2CH3

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).

Draw the hydrogen bonding that takes place between

(a) two molecules of ethanol.

(b) two molecules of propylamine.

(c) a molecule of dimethyl ether and two molecules of water.

(d) two molecules of trimethylamine and a molecule of water.

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
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