Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 5, Problem 17E

(a)

Interpretation Introduction

Interpretation:The curved arrows for acid-base reaction below should be added.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 17E , additional homework tip  1

Concept introduction:According to Bronsted-Lowry concept, substance that donates proton is termed as acid while that accepts or gains protons is called base. Species formed after loss of protons from acids are known as their respective conjugate bases whereas conjugate acid is produced by addition of protons to base.

(b)

Interpretation Introduction

Interpretation: The alcohol that is stronger acid from below alcoholson the basis of pKa should be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 17E , additional homework tip  2

Concept introduction:The dissociation constant of acid represents strength of acid in solution. It is denoted by Ka . The expression of pKa is as follows:

  pKa=logKa

(c)

Interpretation Introduction

Interpretation: The conjugate base that has lower potential energy in below reactionshould be determined.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 17E , additional homework tip  3

Concept introduction:When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

(d)

Interpretation Introduction

Interpretation: The relation between below exampleand story should be explained.

  Organic Chemistry: A Guided Inquiry, Chapter 5, Problem 17E , additional homework tip  4

Concept introduction:When one single structure is unable to describe all the properties of single molecule, a phenomenon called resonance comes into play. This arises when two or more than two Lewis structures are possible for one molecule. All such structures are called resonating structures and have same placement of atoms in them but these have different locations of bond pairs and lone pairs. The resonating structures are inter-convertible with each other. The resultant of all the resonating or contributing structures is called the resonance hybrid.

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1. An acid-base reaction is shown below. ONa + Base Acid Draw the arrow-pushing mechanism for this reaction. b. Draw the products for the reaction and label them as "conjugate base" and "conjugate I | acid." Be sure to assign formal charges. c. Consider the base and conjugate base. Using your four tools, identify the weakest conjugate base and put a box around it. Which tool did you use to determine your answer? d. Using the pKa chart in you lecture notes, label the acid and conjugate acid with their pK, values. Which functional group is the stronger acid? e. Equilibrium moves away from the stronger acid (it wants to dissociate) and toward the more stable conjugate base (lower energy side). Based on your answers to the previous questions, which side of the reaction is favored by equilibrium, left or right? HIN:
spring 4.) а. and then provide a BRIEF rationale. [DO NOT say because it's more acidic...this is not a rationale...] Circle the more acidic proton, Hạ or Hb, on each molecule below, draw the most stable conjugate base, Rationale: На N Hb most stable conjugate base ОНа SHb most stable conjugate base b.) a BRIEF rationale. [DO NOT say because it's more basic...this is not a rationale...] Identify the most basic site on each molecule below, draw the most stable conjugate acid, and then provide Rationale: `NH2 most stable conjugate acid HO, most stable conjugate acid
An acid-base reaction is shown below. ONa + Base Acid a. Draw the arrow-pushing mechanism for this reaction. b. Draw the products for the reaction and label them as "conjugate base" and "conjugate acid." Be sure to assign formal charges. c. Consider the base and conjugate base. Using your four tools, identify the weakest conjugate base and put a box around it. Which tool did you use to determine your answer? d. Using the pKa chart in you lecture notes, label the acid and conjugate acid with their pKa values. Which functional group is the stronger acid? e. Equilibrium moves away from the stronger acid (it wants to dissociate) and toward the more stable conjugate base (lower energy side). Based on your answers to the previous questions, which side of the reaction is favored by equilibrium, left or right?

Chapter 5 Solutions

Organic Chemistry: A Guided Inquiry

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