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Write equations for the following acid–base reactions.

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 18P Chapter 1

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 18P

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any resonance stabilization. Predict whether the equilibrium favors the reactants or products. If in doubt, you can consult Appendix 4 for acids not shown in Table 1-5.

Step-by-Step Solution:

Solution 18P :

Step 1:

A resonance form is another way of drawing a Lewis dot structure for a compound when there is more than one possibility of placing valence or lone pairs of electrons, but the atoms in the resonance forms should have identical position. Equivalent Lewis structures of same compound are called resonance forms.

The arrows in the diagrams below shows the movement of the electrons.

Step 2:

CH3CH2OH + CH3NH- :

        CH3CH2OH is a strong acid. CH3NH-  is a strong base. The following would be the acid base reaction :

Looking at the electron clouds or lone pair of electrons of atoms on both side, we see there is more number of lone pair of electrons on products side and hence, there is more disturbance on the products side. Therefore, the equilibrium favours the products.

Step 2:

CH3CH2COOH + CH3NHCH3 :

CH3CH2COOH is a strong acid. CH3NHCH3  is a strong base. The following would be the acid base reaction :

Looking at the electron clouds or lone pair of electrons of atoms on both side, we see there is more number of lone pair of electrons on products side and hence, there is more disturbance on the products side. Therefore, the equilibrium favours the products.

Step 3 :

CH3OH + H2SO4 :

CH3OH is a strong base. H2SO4 is a strong acid. The following would be the acid base reaction :

Looking at the electron clouds or lone pair of electrons of atoms on both side, we see there is more number of lone pair of electrons on products side and hence, there is more disturbance on the products side. Therefore, the equilibrium favours the products.

Step 4:

NaOH + H2S :

NaOH is a strong base. H2S is a strong acid. The following would be the acid base reaction :

                

Looking at the electron clouds or lone pair of electrons of atoms on both side, we see there is more number of lone pair of electrons on products side and hence, there is more disturbance on the products side. Therefore, the equilibrium favours the products.  

Step 5:

CH3NH3+ + CH3O-  :

CH3NH3 is a strong acid.  CH3O is a strong base. The following would be the acid base reaction :

Looking at the electron clouds or lone pair of electrons of atoms on both side, we see there is more number of lone pair of electrons on products side and hence, there is more disturbance on the products side. Therefore, the equilibrium favours the products.  

Step 6 of 10

Chapter 1, Problem 18P is Solved
Step 7 of 10

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

The full step-by-step solution to problem: 18P from chapter: 1 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 18P from 1 chapter was answered, more than 1190 students have viewed the full step-by-step answer. This full solution covers the following key subjects: acids, label, any, appendix, base. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. The answer to “Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any resonance stabilization. Predict whether the equilibrium favors the reactants or products. If in doubt, you can consult Appendix 4 for acids not shown in Table 1-5.” is broken down into a number of easy to follow steps, and 42 words.

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