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Chapter 2: Q5TP (page 82)

Which is the stronger acid?

a. CH3OH or CH3CH3

b. CH3OH or HF

c. CH3NH2 or HF

d. CH3NH2 or CH3OH

Short Answer

Expert verified

a. CH3OH

b. HF

c. HF

d. CH3OH

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.Strength of acid is determined by the stability of its conjugate base.

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

f. Electronegativity = sp>sp2>sp3

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

02

(a) Reason

CH3OH has less pka value than CH3CH3so CH3OH is a stronger acid.

03

(b) Reason

F is the most electronegative, so HF is a stronger acid than CH3OH.

04

(c) Reason

F is the most electronegative, so HF is a stronger acid than CH3NH2.

05

(d) Reason

CH3NH2 is attached to this proton attached to nitrogen. In CH3OH, proton is attached to oxygen. Oxygen is more electronegative than nitrogen so CH3OH is the stronger acid.

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Most popular questions from this chapter

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-?

Rank the following compounds from strongest to weakest acid

CH3CH2OH CH3CH2NH2 CH3CH2SH CH3CH2CH3

a. Write an equation showing CH3OH reacting with NH3and an equation showing reacting with HCl.

b. Write an equation showing NH3reacting as an acid with CH3O-and an equation showing it reacting as a base with HBr.

Are the following body fluids acidic or basic?

  1. Bile (pH=8.4)
  2. Urine (pH=5.9)
  3. Spinal fluid (pH=7.4)

Question:Draw the products of the acid鈥揵ase reaction when

a. HCl is the acid and NH3 is the base.

b. H2O is the acid and -NH2 is the base.
See all solutions

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