Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 20, Problem 49P
Interpretation Introduction
Interpretation:
The structure of compound that has molecular weight
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
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.
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An aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made:
A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution.
B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below.
C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K.
D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields.
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22. A compound with the molecular formula C8H8O produces an IR spectrum with signals at 3063, 1686, and 1646 cm-1. The 1H NMR spectrum of this compound exhibits a singlet at 2.6ppm(l=3H), and a multiplet at 7.5(l= 5H). Draw the structure and give the common name of this compound . Show the correlations between the structure and spectra.
An unknown compound has the molecular formula C6H12O2. The compound shows a strong peak in its IR spectrum at 1700 cm-1. The 1H NMR data of the compound is given in the graph. Which structure corresponds to the unknown compound?
Chapter 20 Solutions
Organic Chemistry - Standalone book
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.3 - Prob. 3PCh. 20.4 - Prob. 4PCh. 20.5 - Prob. 5PCh. 20.8 - Prob. 6PCh. 20.8 - Prob. 7PCh. 20.8 - Prob. 8PCh. 20.9 - Prob. 9PCh. 20.9 - Prob. 10P
Ch. 20.9 - Prob. 11PCh. 20.9 - Prob. 12PCh. 20.10 - Prob. 13PCh. 20.10 - Prob. 14PCh. 20.11 - Prob. 15PCh. 20.11 - Prob. 16PCh. 20.11 - Prob. 17PCh. 20.12 - Prob. 18PCh. 20.12 - Prob. 19PCh. 20.12 - Prob. 20PCh. 20.12 - Prob. 21PCh. 20.13 - Prob. 22PCh. 20.13 - Prob. 23PCh. 20.14 - Prob. 24PCh. 20.15 - Prob. 25PCh. 20.16 - Prob. 26PCh. 20.17 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Write a structural formula for the principal...Ch. 20 - Prob. 32PCh. 20 - Prob. 33PCh. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - The preparation of the sex pheromone of the...Ch. 20 - Prob. 44PCh. 20 - Suggest a reasonable explanation for each of the...Ch. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - A compound has a molecular formula of C8H14O4, and...Ch. 20 - Prob. 51PCh. 20 - Prob. 52DSPCh. 20 - Prob. 53DSPCh. 20 - Prob. 54DSPCh. 20 - Prob. 55DSPCh. 20 - Prob. 56DSPCh. 20 - Thioesters Thioesters have the general formula ....Ch. 20 - Prob. 58DSP
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- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardKetones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardAn unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compoundarrow_forward
- What is the structure of the compound with the formula C5H12O, if it has a strong broad IR signal centered near 3330 cm-2, and the 1H-NMR spectrum is: 0.91 ppm (3H triplet) 1.19 ppm (6H singlet) 1.50 ppm (2H quartet) 2.24 ppm (1H singlet)arrow_forwardAssume a compound with the formula C4H8O. a) How many double bonds and/or rings does your compound contain? b) If your compound shows an infrared absorption peak at 1715 cm-1, what functional group does it have? c) If your compound shows a single 1H NMR absorption peak at 2.1 δ, what is its structure?arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forward
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