Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 1, Problem 1.64P
Interpretation Introduction

(a)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. Multiple bonds are not shown explicitly in the condensed structure. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis, in the condensed formula, represents that the repetitive unit is attached to the previous carbon atom. The CO2 notation denotes a carbon atom that is doubly bonded to one oxygen atom and singly bonded to another. Rings are generally shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  1

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  2

In the given line structure, there is a five carbon chain, with a carbon-carbon double bond and with a hydroxyl group. Each carbon atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. Multiple bonds are not shown explicitly in the condensed formula. Each carbon atom has a maximum of four bonds while each oxygen atom should have a maximum of two bonds. A parenthesis must be used for the carbon atom having three different groups attached. Thus, the hydroxyl group attached to the carbon atom must be shown in the parenthesis.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  3

Conclusion

The condensed structure for the given line structure is shown in Figure 2 above.

Interpretation Introduction

(b)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each carbon atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. The CO2 notation denotes a carbon atom that is doubly bonded to one oxygen atom and singly bonded to another. Rings are generally shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  4

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  5

In the given line structure, there is a five carbon chain, with two chlorine atoms attached to one of the carbon atoms of the chain. Each carbon atom should have a maximum of four bonds while each oxygen atom should have a maximum of two bonds. A parenthesis must be used for the carbon atom having three different groups attached. Thus, the -CH2 groups are shown as (-CH2)n with n being the number of units. The two chlorine atoms are also shown in the parenthesis. Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  6

Conclusion

The condensed structure for the given line structure is shown in Figure 4 above.

Interpretation Introduction

(c)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. Multiple bonds are not shown explicitly in the condensed structure. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. The CO2 notation denotes a carbon atom that is doubly bonded to one oxygen atom and singly bonded to another. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  7

In the given line structure, there is a chain of four carbon atoms on the left side of a singly bonded oxygen. Each carbon atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. Multiple bonds are not shown explicitly in the condensed structure while an ethyl fragment is present at the right side of the singly bonded oxygen atom. The CO2 notation denotes a carbon atom that is doubly bonded to one oxygen atom and singly bonded to another. There are two methyl groups present at one end of the chain, thus, a parenthesis must be used to denote this group.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  8

Conclusion

The condensed structure for the given line structure is shown in Figure 6 above.

Interpretation Introduction

(d)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Multiple bonds in the ring and outside the ring are shows as they are. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  9

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  10

In the given line structure, a five membered ring containing a nitrogen atom is present. While writing a condensed formula, a ring is shown in its partial condensed formula. One of the carbon atoms in the ring forms a double bond with the oxygen atom which is shown as is.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  11

Conclusion

The condensed structure for the given line structure is shown in Figure 8 above.

Interpretation Introduction

(e)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly, followed immediately by the number of hydrogen atoms that are bonded to it. Multiple bonds are not shown explicitly in the condensed structure. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. Rings are generally shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  12

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  13

In the above line structure, the disubstituted benzene ring is present. One substituent of the benzene ring is a three carbon chain with an internal triple bond. The other substituent is a methoxy group, -OCH3, group. Each carbon atom in the ring as well as in the substituent is shown explicitly followed by the number of hydrogen atoms directly attached to it. Multiple bonds, if present outside the ring, are not shown explicitly.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  14

Conclusion

The condensed structure for the given line structure is shown in Figure 10 above.

Interpretation Introduction

(f)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly, followed immediately by the number of hydrogen atoms that are bonded to it. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom. A formal charge is shown explicitly on the atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  15

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  16

The above line structure is a structure for a cation. A carbocation is a carbon bearing a positive formal charge which is explicitly shown in the condensed formula. A six membered carbon ring with alternate double and single bonds is present and is shown as a partial condensed structure.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  17

Conclusion

The condensed structure for the given line structure is shown in Figure 12 above.

Interpretation Introduction

(g)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly, followed immediately by the number of hydrogen atoms that are bonded to it. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom. A formal charge is shown explicitly on the atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  18

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  19

The above line structure is a structure for an anion. A six membered carbon ring with single bonds is present. Each carbon atom is written explicitly followed immediately by the number of hydrogen atoms that are bonded to it. The negative charge on the carbon atom is shown explicitly. The two methyl groups attached to the carbon bearing a negative charge are shown in the parenthesis.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  20

Conclusion

The condensed structure for the given line structure is shown in Figure 14 above.

Interpretation Introduction

(h)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. Each non-hydrogen atom is written explicitly, followed immediately by the number of hydrogen atoms that are bonded to it. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom. A formal charge is shown explicitly on the atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  21

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  22

The above line structure is a six membered ring with a negative charge on one of the carbon atoms of the ring. The carbon bearing a negative charge is shown as is. The ring is monosubstituted with an isopropyl group. The two methyl groups in the isopropyl fragments is shown with the help of parenthesis.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  23

Conclusion

The condensed structure for the given line structure is shown in Figure 16 above.

Interpretation Introduction

(i)

Interpretation:

Given line structure is to be drawn using condensed formula.

Concept introduction:

The condensed formula indicates how the atoms should be connected in a given molecule. To arrive at a total charge of zero, each carbon should have a maximum of four bonds while each oxygen should have a maximum of two bonds and two lone pairs. A parenthesis in the condensed formula represents that the repetitive unit is attached to the previous carbon atom. The CO2 notation denotes a carbon atom that is doubly bonded to one oxygen atom and singly bonded to another. Rings are generally now shown in their condensed formulas, but they are commonly shown in their partially condensed form. Parentheses are also used to clarify when two or three groups are attached to the same carbon atom.

Expert Solution
Check Mark

Answer to Problem 1.64P

For the given line structure, the condensed structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  24

Explanation of Solution

The given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  25

The above line structure is a chain of five carbon atoms. One end of the chain has carboxylate ion, in which the oxygen carries a negative charge. The other end of the chain has a nitrogen atom with three hydrogen atoms directly attached to it and carrying a positive charge. Formal charges on atoms are shown explicitly.

Thus, the condensed structure for the given line structure is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 1, Problem 1.64P , additional homework tip  26

Conclusion

The condensed structure for the given line structure is shown in Figure 18 above.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Using just a periodic table (not a table of electronegativities), decide which of these is likely to be the most polar bond. Explain your answer! (a) C-F (b) S-F (c) Si-F (d) O-F
Assignment 3.16 Which of these molecules are polar? Show the direction of the molecular dipole by using an arrow with a crossed tail. (a) H2S (b) HCN (c) C2H6
Draw a Lewis Structure for each of the following species and assign formal charge where appropriate. Using electronegative values from the period table that was provided identify polar covalent bonds and label the atoms δ+ and δ−. For each of the molecules indicate whether or not it has a dipole moment. (a)CH5N (b) HCN (c) H2CO (d) CH3NC(e) CH3SOCH3 (f) H6BN

Chapter 1 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Prob. 1.14PCh. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Prob. 1.24PCh. 1 - Prob. 1.25PCh. 1 - Prob. 1.26PCh. 1 - Prob. 1.27PCh. 1 - Prob. 1.28PCh. 1 - Prob. 1.29PCh. 1 - Prob. 1.30PCh. 1 - Prob. 1.31PCh. 1 - Prob. 1.32PCh. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Prob. 1.35PCh. 1 - Prob. 1.36PCh. 1 - Prob. 1.37PCh. 1 - Prob. 1.38PCh. 1 - Prob. 1.39PCh. 1 - Prob. 1.40PCh. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - Prob. 1.56PCh. 1 - Prob. 1.57PCh. 1 - Prob. 1.58PCh. 1 - Prob. 1.59PCh. 1 - Prob. 1.60PCh. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Prob. 1.68PCh. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Prob. 1.75PCh. 1 - Prob. 1.76PCh. 1 - Prob. 1.77PCh. 1 - Prob. 1.78PCh. 1 - Prob. 1.79PCh. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.1YTCh. 1 - Prob. 1.2YTCh. 1 - Prob. 1.3YTCh. 1 - Prob. 1.4YTCh. 1 - Prob. 1.5YTCh. 1 - Prob. 1.6YTCh. 1 - Prob. 1.7YTCh. 1 - Prob. 1.8YTCh. 1 - Prob. 1.9YTCh. 1 - Prob. 1.10YTCh. 1 - Prob. 1.11YTCh. 1 - Prob. 1.12YTCh. 1 - Prob. 1.13YTCh. 1 - Prob. 1.14YTCh. 1 - Prob. 1.15YTCh. 1 - Prob. 1.16YTCh. 1 - Prob. 1.17YT
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Stoichiometry - Chemistry for Massive Creatures: Crash Course Chemistry #6; Author: Crash Course;https://www.youtube.com/watch?v=UL1jmJaUkaQ;License: Standard YouTube License, CC-BY
Bonding (Ionic, Covalent & Metallic) - GCSE Chemistry; Author: Science Shorts;https://www.youtube.com/watch?v=p9MA6Od-zBA;License: Standard YouTube License, CC-BY
General Chemistry 1A. Lecture 12. Two Theories of Bonding.; Author: UCI Open;https://www.youtube.com/watch?v=dLTlL9Z1bh0;License: CC-BY