Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 16, Problem 16.10P

Draw the structure consistent with each description.

a. ( 2 E , 4 E ) octa 2 , 4 diene in the s trans conformation

b. ( 3 E , 5 Z ) nona 3 , 5 diene in the s trans conformation

c. ( 3 Z , 5 Z ) 4 , 5 dimethyldeca 3 , 5 diene . Draw both the s-cis and s-trans conformations.

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The structure corresponding to (2E,4E)octa2,4diene in the strans conformation is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

The prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is Z isomer.

Answer to Problem 16.10P

The structure corresponding to (2E,4E)octa2,4diene in the strans conformation is shown as:

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  1

Explanation of Solution

The given name is (2E,4E)octa2,4diene. The word root used in this is oct. It means structure contains eight carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. The prefix used is E. Thus, it means that the two double bonds are present on the opposite side.

Thus, the correct structure of (2E,4E)octa2,4diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  2

Figure 1

Conclusion

The structure corresponding to (2E,4E)octa2,4diene in the strans conformation is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The structure corresponding to (3E,5Z)nona3,5diene in the scis conformation is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

The prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E or trans isomer, whereas when two higher priority groups are present on the same side then it is Z or cis isomer.

Answer to Problem 16.10P

The structure corresponding to (3E,5Z)nona3,5diene in the strans conformation is shown as:

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  3

Explanation of Solution

The given name is (3E,5Z)nona3,5diene. The word root used in this is non. It means structure contains nine carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. The prefix used are E and Z. Thus, it means that the stereochemistry at one double bond is trans and at other is cis.

Thus, the correct structure of (3E,5Z)nona3,5diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  4

Figure 2

Conclusion

The structure corresponding to (3E,5Z)nona3,5diene in the strans conformation is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The structure corresponding to strans and scis conformation of (3Z,5Z)4,5dimethyldeca3,5diene is to be drawn.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing structural formula from IUPAC are:

1. First identify the word root for the given compound.

2. The suffix used in the compound like –ene.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

The prefix E and Z depends upon the location of the higher priority groups. When two higher priority groups are present on the opposite side then it is an E isomer, whereas when two higher priority groups are present on the same side then it is Z isomer.

Answer to Problem 16.10P

The structures corresponding to strans and scis conformation of (3Z,5Z)4,5dimethyldeca3,5diene are:

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  5

Explanation of Solution

The given name is (3Z,5Z)4,5dimethyldeca3,5diene. The word root used in this is dec. It means structure contains ten carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. The prefix used is Z. Thus, it means that the two double bonds are present on the same side.

Thus, the correct structure to strans and scis conformation of (3Z,5Z)4,5dimethyldeca3,5diene is shown below.

Organic Chemistry, Chapter 16, Problem 16.10P , additional homework tip  6

Figure 3

Conclusion

The structure corresponding to strans and scis conformation of (3Z,5Z)4,5dimethyldeca3,5diene is shown in Figure 3.

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 the structure consistent with each description. a.(2E,4E)-octa-2,4-diene in the s-trans conformation b.(3E,5Z)-nona-3,5-diene in the s-cis conformation c.(3Z,5Z)-4,5-dimethyldeca-3,5-diene. Draw both the s-cis and s-trans conformations.
Rank the following groups in order of decreasing priority. −CH=CH2, −CH3, −C≡CH, −H
Focus only on carbon 1 For carbon 1, which group has the highest priority? a,b,c or d?why? What enantiomer is carbon 1? R or S?

Chapter 16 Solutions

Organic Chemistry

Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound. a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75P
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
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
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