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Chapter 2: Q4TP (page 82)

Which of the reactions in Problem 3 favour formation of the reactants, and which favour formation of the products?

(a) CH3N+H3+H2O

(b) HBr+CH3OH

(c) CH3NH3+HO-

(d) CH3NH2+CH3OH

(The pKavalues can be found in Sections 2.3 and 2.6.)

Short Answer

Expert verified

The following reactions are:

a. CH3NH3++H2翱鈬婥贬3NH2 + H3O+=reactants

b. HBr +CH3翱贬鈬婥贬3OH2+ + Br-=products

c. CH3NH3++ OH-鈬婥贬3NH2+ H2O=products

d.CH3NH2+ CH3翱贬鈬婥贬3NH3+ + CH3O-=reactants

Step by step solution

01

Factors affecting acidity

a. As we go down the group, the electron cloud becomes larger, and there is less attraction on the protons. A proton can be easily removed, so that the acid is stronger.

b. Hybridization = In (stronger acid hybridization follows the order sp>sp2>sp3)

c. values are as follows: protonated alcohols, protonated carboxylic acids, and protonated water < 0; carboxylic acids ~5; protonated amines ~10; alcohols and water ~15.

d.The strength of an acid is determined by the stability of its conjugate base.

e.When atoms are of similar size, the strong acid is one which has its hydrogen attached to the more electronegative element.

f. Electronegativity = sp>sp2>sp3

g.When atoms are of different size, the strong acid is one which has hydrogen attached to the largest atom.

02

(a) Explanation and final answer

As protonated amine has more pkavalue, the hydronium ion reaction will proceed towards reactants.

03

(b) Explanation and final answer

HBr is more acidic so the reaction will proceed towards the products.

04

(c) Explanation final answer

Protonated amine has less pka value than water so the reaction will proceed towards the products.

05

(d) Explanation final answer

Protonated amine has less pka value than alcohol so the reaction will proceed towards the reactants.

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Most popular questions from this chapter

a. For each of the acid-base reactions in section 2.3, compare the pKa values of the acids on either side of the equilibrium arrows to prove that the equilibrium lies in the direction indicated. (The pKa values you need are found in section 2.3 or in problem 13)

b. Do the same for the acid-base reaction in section 2.1

Which is the stronger acid?

a. CH3CH3 or HC 鈮H

b. H2C= CH2or HC鈮� CH

c. H2C =CH2 or CH3CH3

Butyric acid, the compound responsible for the unpleasant odor and taste of sour milk, has a pKa value of 4.82. What is its Ka value? Is it a stronger acid or a weaker acid than vitamin C?

Ethyne (HC鈮�CH) has a pKa value of 25, water has a pKa value of 15.7, and ammonia (NH3) has a pKa value of 36. Draw the equation, showing equilibrium arrows that indicate whether reactants or products are favored, for the acid-base reaction of ethyne with

a.OH-

b.NH2-

c. Which would be a better base to use if you wanted to remove a proton from ethyne, OH-or NH2-?

Draw the products of the following acid鈥揵ase reactions:

a. CH3NH3++H2O

b. HBr +CH3OH

c. CH3NH3++ OH-

d.CH3NH2+ CH3OH
See all solutions

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