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Consider the following proposed Bronsted-Lowry acid-base reactions. In each case, draw the products of a transfer of the most acidic proton on the acid to the most basic site on the base. Use Appendix 4 to find the pKa values for the acids and the pKb values for the bases. Then determine which side of the reaction is favored, either reactants of products.

(a)

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Bronsted – Lowry concept of acid and base

According to Bronsted-Lowry, an acid can be defined as any substance (molecule or ion) that has the tendency to donate a proton (H+) to any substance whereas a base can be defined as any substance (molecule or ion) that has the tendency to accept a proton (H+) from any other substance.

02

Conjugate acid-base pair

The remaining part of an acid after losing a proton (H+) will have a tendency to accept a proton (H+). Hence, it will behave as a base. These pairs of substances that differ from one another by a proton (H+) are known as conjugate acid-base pairs. Consider a general example of an acid:

03

Step 3:  Ka and pKa  , Kb and  pKb

Ka is known as the acid dissociation constant and its value indicates the relative strength of the acid. pKa is defined as the negative logarithm (base 10 ) of Ka . Mathematically, pKa =-logKa . pKa value of strong acids is usually zero or even negative while the pKa value of weaker acids are greater than 4.

Kb is known as the base dissociation constant and its value indicates the relative strength of the base. pKb is defined as the negative logarithm (base 10 ) of pKb . Mathematically, pKb =-logKb .

04

Equilibrium positions of acid-base reactions

The formation of weaker acid and weaker base is favored by the acid-base equilibrium. Larger pKa means weaker is the acid while larger pKb means weaker is the base. Both the weaker acid and weaker base exist as either reactants or products and they are always present on the same side of the equation.

05

Prediction of equilibrium

(a)

The weaker acid and weaker base are both present in the reactant side, hence the equilibrium will favor the reactants.

(b)

The weaker acid and weaker base are both present in the product side, hence the equilibrium will favor the products.

(c)

The weaker acid and weaker base are both present in the reactant side, hence the equilibrium will favor the reactants.

(d)

The weaker acid and weaker base are both present in the reactant side, hence the equilibrium will favor the reactants.

(e)

The weaker acid and weaker base are both present in the product side, hence the equilibrium will favor the products.

(f)

The weaker acid and weaker base are both present in the product side, hence the equilibrium will favor the products.

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Most popular questions from this chapter

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

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).

Many naturally occurring compounds contain more than one functional group. Identify the functional groups in the following compounds

  1. Penicillin G is a naturally occurring antibiotic.
  2. Dopamine is the neurotransmitter that is deficient in Parkinson’s disease.
  3. Capsaicin gives the fiery taste to chili peppers.
  4. Thyroxine is the principal thyroid hormone.
  5. Testosterone is a male sex hormone.

Predict which compound in each pair has the higher boiling point. Explain your prediction.

(a)

CH3CH2CH2OCH3 or CH3CH2CH2(OH)CH3

(b)

CH3CH2CH2CH2CH3 or CH3CH2CH2CH2CH2CH3

(c)

CH3CH2CH2CH2CH2CH3 or (CH2)3CHCH2CH2CH3

(d)

CH3CH2CH2CH2CH2CH3 or CH3CH2CH2CH2CH2CH2Cl

(e)

(f)

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