ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 16, Problem 16.37P

Draw the structure of each compound.

a. ( Z ) penta 1 , 3 diene in the s trans conformation.

b. ( 2 E , 4 Z ) 1 bromo 3 methylhexa 2 , 4 diene

c. ( 2 E , 4 E , 6 Z ) octa 2 , 4 , 6 triene

d. ( 2 E , 4 E ) 3 methylhexa 2 , 4 diene  in the s cis conformation.

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The structure corresponding to (Z)penta1,3diene 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 16.37P

The structure corresponding to (Z)penta1,3diene in the strans conformation is,

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  1

Explanation of Solution

The given name is (Z)penta1,3diene. The word root used in this is pent. It means structure contains five 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. It means that two higher priority groups are present on the same side. The given compound has trans conformation. Thus, the correct structure of (Z)penta1,3diene is shown below.

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  2

Figure 1

Conclusion

The structure corresponding to (Z)penta1,3diene in the strans conformation is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The structure corresponding to (2E,4Z)1bromo3methylhexa2,4diene 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 16.37P

The structure corresponding to (2E,4Z)1bromo3methylhexa2,4diene is,

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  3

Explanation of Solution

The given name is (2E,4Z)1bromo3methylhexa2,4diene. The word root used in this is hex. It means structure contains six 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 (2E,4Z)1bromo3methylhexa2,4diene is shown below.

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  4

Figure 2

Conclusion

The structure corresponding to (2E,4Z)1bromo3methylhexa2,4diene is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The structure corresponding to (2E,4E,6Z)octa2,4,6triene 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 16.37P

The structure corresponding to (2E,4E,6Z)octa2,4,6triene is,

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  5

Explanation of Solution

The given name is (2E,4E,6Z)octa2,4,6triene. 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. It means that two higher priority groups are present on the same side. Thus, the correct structure to (2E,4E,6Z)octa2,4,6triene is shown below.

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  6

Figure 3

Conclusion

The structure corresponding to (2E,4E,6Z)octa2,4,6triene is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The structure corresponding to (2E,4E)3methylhexa2,4diene scis 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:

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

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

6. 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 16.37P

The structure corresponding to (2E,4E)3methylhexa2,4diene in scis is,

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  7

Explanation of Solution

The given name is (2E,4E)3methylhexa2,4diene. The word root used in this is hex. It means structure contains six carbon atoms. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methyl substituent is attached to the third carbon atom. The prefix used is E. It means that two higher priority groups are present on the opposite side. Thus, the correct structure to (2E,4E)3methylhexa2,4diene is shown below.

ORGANIC CHEMISTRY, Chapter 16, Problem 16.37P , additional homework tip  8

Figure 4

Conclusion

The structure corresponding to (2E,4E)3methylhexa2,4diene in scis is shown in Figure 4.

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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
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