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

Concept explainers

Question
Chapter 7.SE, Problem 22VC
Interpretation Introduction

a)

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  1

Interpretation:

To name the alkene given and to draw its skeletal structure.

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.

In skeletal structures the carbon and hydrogen atoms are not usually shown. Instead carbon atoms are assumed to be at each intersection of two lines and at the end of each line. Hydrogen atoms required are fitted mentally having in mind the valence of carbon is four. Atoms other than carbon and hydrogen are shown.

To name:

The alkene given and to draw its skeletal structure.

Expert Solution
Check Mark

Answer to Problem 22VC

The IUPAC name of the compound is 2, 4, 5-trimethyl-2-hexene. Its skeletal structure is,

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  2

Explanation of Solution

The compound given has a continuous chain of six carbons with a double bond between C2 and C3 and three methyl substituents on C2, C4 and C5. Hence the name 2, 4, 5-trimethyl-2-hexene.

Conclusion

The IUPAC name of the compound is 2, 4, 5-trimethyl-2-hexene. Its skeletal structure is,

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  3

Interpretation Introduction

b)

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  4

Interpretation:

To name the alkene given and to draw its skeletal structure.

Concept introduction:

The maximum number of carbons in the ring is counted. Based on the name of the parent cycloalkane - the cycloalkene is named with the suffix -ene. The cycloalkane is numbered such that the double bond is in between C1 & C2 and the first substituent has the lowest number possible. Usually the position of a double bond is not shown in the name because it is always between C1 & C2. In dienes and trienes, however the position of double bonds is shown.

In skeletal structures the carbon and hydrogen atoms are not usually shown. Instead carbon atoms are assumed to be at each intersection of two lines and at the end of each line. Hydrogen atoms required are fitted mentally having in mind the valence of carbon is four. Atoms other than carbon and hydrogen are shown.

To name:

The alkene given and to draw its skeletal structure.

Expert Solution
Check Mark

Answer to Problem 22VC

The IUPAC name of the compound is 1-ethyl-3, 3-dimethylcyclohexene. Its skeletal structure is,

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  5

Explanation of Solution

The compound given has a six membered ring with an ethyl group on C1 and two methyl groups both on C3. Hence the name is 1-ethyl-3, 3-dimethylcyclohexene.

Conclusion

The IUPAC name of the compound is 1-ethyl-3, 3-dimethylcyclohexene. Its skeletal structure is,

Organic Chemistry, Chapter 7.SE, Problem 22VC , additional homework tip  6

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
Draw a structural formula for the most stable carbocation with each molecular formula. Q.) C5H11+
Reaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yieldsmethyl tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous to that of acid- catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.
a. Draw the structures and give the common and systematic names for alkynes with molecular formula C7H12. Ignore stereosiomers. (Hint: There are 14.) b. How many would there be if stereoisomers are included?

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
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
  • Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
  • Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning