Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.56P

Propose a structure consistent with each set of data.

a. Compound A:

Molecular formula: C 8 H 10 O IR absorptions at 3150-2850, cm 1 1 H NMR data: 1 .4 ( triplet, 3 H ) , 3.9 5 ( quartet, 2 H ) , and 6.8 7. 3 ( multiplet, 5 H ) ppm

b. Compound B:

Molecular formula: C 9 H 10 O 2 IR absorptions at 1669 cm 1 1 H NMR data: 2 .5 ( singlet, 3 H ) , 3.8 ( singlet, 3 H ) , 6.9 ( doublet, 2 H ) , and 7.9 ( doublet, 2 H ) ppm

Expert Solution
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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 17.56P

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

Organic Chemistry-Package(Custom), Chapter 17, Problem 17.56P , additional homework tip  1

Explanation of Solution

The given sets of IR and 1HNMR data for Compound A are,

Molecularformula:C8H10OIRabsorptionsat3150-2850,cm11HNMRdata:1.4(triplet,3H),3.95(quartet,2H),and6.87.3(multiplet,5H)ppm

Information from IR data:

The IR absorption at 31502850cm1 suggests the presence of Csp2H, and Csp3H bonds.

Information from 1HNMR data:

The observed chemical shift value at 1.4(triplet,3H)ppm suggests the presence of 2H's on the adjacent carbon.

The observed chemical shift value at 3.95(quartet,2H)ppm suggests the presence of 3H's on the adjacent carbon.

The observed chemical shift value at 6.87.3(multiplet,5H)ppm suggests the presence of 5H's on the benzene ring.

The possible structure of the Compound A, based on the above analysis is,

Organic Chemistry-Package(Custom), Chapter 17, Problem 17.56P , 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 17.56P

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

Organic Chemistry-Package(Custom), Chapter 17, Problem 17.56P , additional homework tip  3

Explanation of Solution

The given sets of IR and 1HNMR data for Compound B are,

Molecularformula:C9H10O2IRabsorptionsat1669cm11HNMRdata:2.5(singlet,3H),3.8(singlet,3H),6.9(doublet,2H),and7.9(doublet,2H)ppm

Information from IR data:

The IR absorption at 31502850cm1 suggests the presence of 1669cm1.

Information from 1HNMR data:

The observed chemical shift value at 2.5(singlet,3H)ppm suggests the presence of methyl group with no hydrogen atom on the adjacent carbon.

The observed chemical shift value at 3.8(singlet,3H)ppm suggests the presence of methyl group with no hydrogen atom on the adjacent carbon.

The observed chemical shift values at 6.9(doublet,2H),and7.9(doublet,2H)ppm, suggest the presence of 4H's(2H'seach) on the benzene ring.

The possible structure of the Compound B, based on the above analysis is,

Organic Chemistry-Package(Custom), Chapter 17, Problem 17.56P , additional homework tip  4

Figure 2

Conclusion

A structure consistent with the given set of data is shown in Figure 2.

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Chapter 17 Solutions

Organic Chemistry-Package(Custom)

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