ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.55P

Propose a structure consistent with each set of data.

a. C 10 H 14 : IR absorptions at 3150 2850 , 1600 , and 1500 cm 1

Chapter 17, Problem 17.55P, 17.55	 Propose a structure consistent with each set of data.






 , example  1

b. C 9 H 12 : 13 C NMR signals at 21 , 127 , and 138 ppm

Chapter 17, Problem 17.55P, 17.55	 Propose a structure consistent with each set of data.






 , example  2

c. C 8 H 10 : IR absorptions at 3108 2875 , 1606 , and 1496 cm 1

Chapter 17, Problem 17.55P, 17.55	 Propose a structure consistent with each set of data.






 , example  3

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: A structure consistent with the given set of data is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 17.55P

A structure consistent with the given set of data is shown below.

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  1

Explanation of Solution

The given set of IR data is,

C10H14:IRabsorptionsat31502850,1600,and1500cm1

Information from IR data:

The IR absorption at 31502850cm1 suggests the presence of Csp2H, and Csp3H bonds, and absorptions at 1500,and1600cm1 suggests the presence of benzene ring.

Information from 1HNMR data:

The observed chemical shift value at 1.3ppm(doublet) for 6H suggests the presence of one H on the adjacent carbon.

The observed chemical shift value at 2.4ppm(singlet) for 3H suggests the presence of one methyl group (no H on the adjacent carbon) on the benzene ring.

The observed chemical shift value at 3.2ppm(septet) for 1H suggests the presence of 3H's on each of the adjacent two carbons.

The observed chemical shift value at 7.2ppm(multiplet) for 4H suggests the presence of 4H's on the benzene ring.

The possible structure of the compound based on the above analysis is,

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  2

Figure 1

Conclusion

A structure consistent with the given set of data is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: A structure consistent with the given set of data is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 17.55P

A structure consistent with the given set of data is shown below.

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  3

Explanation of Solution

The given set of 13CNMR data is,

C9H12:13CNMRsignalsat21,127,and138ppm

Information from 13CNMR data:

Three signals are observed in 13CNMR spectrum. This means three different types of carbon atoms are present in compound.

The 13CNMR signal at 21,127,and138ppm suggest the presence of given types of carbon atoms.

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  4

Figure 2

Information from 1HNMR data:

The observed chemical shift value at 2.3ppm(singlet) for 9H suggests the presence of three methyl group (no H on the adjacent carbon) on benzene ring.

The observed chemical shift value at 6.9ppm(singlet) for 3H suggests the presence of three deshielded hydrogen atoms on the benzene ring.

The possible structure of the compound based on the above analysis is,

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  5

Figure 3

Conclusion

A structure consistent with the given set of data is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: A structure consistent with the given set of data is to be predicted.

Concept introduction: Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and electromagnetic radiations. Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the functional group. The value of chemical peaks depends upon the chemical environment around the hydrogen atom.

Answer to Problem 17.55P

A structure consistent with the given set of data is shown below.

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  6

Explanation of Solution

The given set of IR data is,

C8H10:IRabsorptionsat31082875,1606,and1496cm1

Information from IR data:

The IR absorption at 31082875cm1 suggest the presence of Csp2H, and Csp3H bonds, and absorptions at 1606,and1496cm1 suggest the presence of benzene ring.

Information from 1HNMR data:

The observed chemical shift value at 1.3ppm(triplet) for 3H suggests the presence of two H's on the adjacent carbon.

The observed chemical shift value at 2.7ppm(quartet) for 2H suggests the presence of three H's on the adjacent carbon.

The observed chemical shift value at 7.4ppm(multiplet) for 5H suggests the presence of five H's on the benzene ring.

The possible structure of the compound based on the above analysis is,

ORGANIC CHEMISTRY, Chapter 17, Problem 17.55P , additional homework tip  7

Figure 4

Conclusion

A structure consistent with the given set of data is shown in Figure 4.

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Chapter 17 Solutions

ORGANIC CHEMISTRY

Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds. a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38 How many electrons does C contain? How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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