Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 7.SE, Problem 38AP

Draw structures corresponding to the following systematic names:

(a) (4E)-2, 4-Dimethyl-l, 4-hexadiene

(b) cis-3, 3-Dimethyl-4-propyl-l, 5-octadiene

(c) 4-Methyl-l, 2-pentadiene

(d) (3E, 5Z)-2, 6-Dimethyl-1, 3, 5, 7-octatetraene

(e) 3-Butyl-2-heptene

(f) trans-2, 2, 5, 5-Tetramethyl-3-hexene

Expert Solution
Check Mark
Interpretation Introduction

a) (4E)-2, 4-Dimethyl-1, 4-hexadiene.

Interpretation:

The structure corresponding to the systematic name (4E)-2, 4-dimethyl-1, 4-hexadiene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–alkene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on. The isomer that has the higher ranked groups on each carbon are on the same side of the double bond is said to have Z configuration. If the higher ranked groups are on opposite sides, the alkene is said to have E configuration.

To draw:

The structure corresponding to the systematic name (4E)-2, 4-dimethyl-1, 4-hexadiene.

Answer to Problem 38AP

The structure corresponding to the systematic name (4E)-2, 4-dimethyl-1, 4-hexadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  1

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with two double bonds between C2 & C3 and C4 & C5. There should be two methyl substituents one on C2 and other on C4. Further higher ranked groups on each carbon should be in the opposite sides of the double bonds.

Conclusion

The structure corresponding to the systematic name (4E)-2, 4-dimethyl-1, 4-hexadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  2

Expert Solution
Check Mark
Interpretation Introduction

b) cis-3, 3-Dimethyl-4-isopropyl-1, 5-octadiene.

Interpretation:

The structure corresponding to the systematic name cis-3, 3-dimethyl-4-isopropyl-1, 5-octadiene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–ene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on. The isomer that has similar groups on each carbon on the same side of the double bond is called as the cis isomer. The isomer that has similar groups on each carbon on the opposite side of the double bond is called as thetrans isomer.

To draw:

The structure corresponding to the systematic name cis-3, 3-dimethyl-4-isopropyl-1, 5-octadiene.

Answer to Problem 38AP

The structure corresponding to the systematic name cis-3, 3-dimethyl-4-isopropyl-1, 5-octadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  3

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with two double bonds between C1 & C2 and C5 & C6. There should be two methyl substituents on C3 and an isopropyl group on C4. Further similar groups in each carbon should be on the same sides of the double bonds.

Conclusion

The structure corresponding to the systematic name cis-3, 3-dimethyl-4-isopropyl-1, 5-octadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  4

Expert Solution
Check Mark
Interpretation Introduction

c) 4-Methyl-1, 2-pentadiene.

Interpretation:

The structure corresponding to the systematic name4-methyl-1, 2-pentadiene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–ene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on.

To draw:

The structure corresponding to the systematic name 4-methyl-1, 2-pentadiene.

Answer to Problem 38AP

The structure corresponding to the systematic name 4-methyl-1, 2-pentadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  5

Explanation of Solution

The name shows that the longest carbon chain should contain five carbons with two double bonds between C1 & C2 and C2 & C3. There should be amethyl substituent on C4.

Conclusion

The structure corresponding to the systematic name 4-methyl-1, 2-pentadiene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  6

Expert Solution
Check Mark
Interpretation Introduction

d) (3E, 5Z)-2, 6-Dimethyl-1, 3, 5, 7-octatetraene.

Interpretation:

The structure corresponding to the systematic name (3E, 5Z)-2, 6-dimethyl-1, 3, 5, 7-octatetraene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–ene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on. The isomer that has the higher ranked groups on each carbon are on the same side of the double bond is said to have Z configuration. If the higher ranked groups are on opposite sides, the alkene is said to have E configuration.

To draw:

The structure corresponding to the systematic name (3E, 5Z)-2, 6-dimethyl-1, 3, 5, 7-octatetraene.

Answer to Problem 38AP

The structure corresponding to the systematic name (3E, 5Z)-2, 6-dimethyl-1, 3, 5, 7-octatetraene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  7

Explanation of Solution

The name shows that the longest carbon chain should contain eight carbons with two double bonds between C2 & C3 and C6 & C7. There should be two methyl substituents one on C2 and other on C6. Further higher ranked groups on C2 & C3 must be placed on the opposite sides of the double bond. The higher ranked groups on C6 & C7 must be placed on the same side of the double bond.

Conclusion

The structure corresponding to the systematic name (3E, 5Z)-2, 6-dimethyl-1, 3, 5, 7-octatetraene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  8

Expert Solution
Check Mark
Interpretation Introduction

e) 3-Butyl-2-heptene.

Interpretation:

The structure corresponding to the systematic name3-butyl-2-heptene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–ene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on.

To draw:

The structure corresponding to the systematic name 3-butyl-2-heptene.

Answer to Problem 38AP

The structure corresponding to the systematic name 3-butyl-2-heptene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  9

Explanation of Solution

The name shows that the longest carbon chain should contain seven carbons with a double bond between C2 & C3. There should be a butyl substituent on C3.

Conclusion

The structure corresponding to the systematic name 3-butyl-2-heptene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  10

Expert Solution
Check Mark
Interpretation Introduction

f) trans-2, 2, 5, 5-Tetramethyl-3-hexene.

Interpretation:

The structure corresponding to the systematic name trans-2, 2, 5, 5-tetramethyl-3-hexene is to be drawn.

Concept introduction:

The longest carbon chain containing the double bond to be chosen. Based on the name of the parent compound–the alkene name ends with the suffix–ene. The chain is to be numbered from the end that gives the lowest number to the carbon in double bond. Substituents are to be numbered according to their positions in the chain and listed alphabetically. The position of the double bond is indicated by giving the number of the first alkene carbon before the name of the parent name. If more than one double bond is present, their positions are indicated with the suffixes -diene, -triene and so on. The isomer that has similar groups on each carbon on the same side of the double bond is called as the cis isomer. The isomer that has similar groups on each carbon on the opposite side of the double bond is called as the trans isomer.

To draw:

The structure corresponding to the systematic name trans-2, 2, 5, 5-tetramethyl-3-hexene.

Answer to Problem 38AP

The structure corresponding to the systematic name trans-2, 2, 5, 5-tetramethyl-3-hexene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  11

Explanation of Solution

The name shows that the longest carbon chain should contain six carbons with a double bond between C3 & C4. There should be four methyl substituents two on C3 and two on C5. Further similar groups in each carbon should be on the opposite sides of the double bonds.

Conclusion

The structure corresponding to the systematic name trans-2,2,5,5-tetramethyl-3-hexene is

Organic Chemistry, Chapter 7.SE, Problem 38AP , additional homework tip  12

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
C7H9N has 4 degrees of unsaturation, what are the possible structures?
Determine the DOU for the following molecules and suggest a structure for each. C5H7Br2ON
Draw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.

Chapter 7 Solutions

Organic Chemistry

Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Prob. 12PCh. 7.5 - Prob. 13PCh. 7.5 - Prob. 14PCh. 7.6 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.10 - Prob. 20PCh. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Prob. 22VCCh. 7.SE - Prob. 23VCCh. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - Prob. 25VCCh. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Prob. 27MPCh. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - Prob. 33MPCh. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - Prob. 35APCh. 7.SE - Prob. 36APCh. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Prob. 39APCh. 7.SE - Prob. 40APCh. 7.SE - Prob. 41APCh. 7.SE - Prob. 42APCh. 7.SE - Prob. 43APCh. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Prob. 45APCh. 7.SE - Prob. 46APCh. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Prob. 48APCh. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Prob. 50APCh. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Prob. 53APCh. 7.SE - Prob. 54APCh. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Prob. 56APCh. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Prob. 58APCh. 7.SE - Prob. 59APCh. 7.SE - Prob. 60APCh. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Prob. 64APCh. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Prob. 67APCh. 7.SE - Prob. 68APCh. 7.SE - Prob. 69APCh. 7.SE - Prob. 70APCh. 7.SE - Prob. 71APCh. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...
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
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License