Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 19, Problem 32P
Interpretation Introduction
Interpretation:
The compounds A and B have to be identified on the basis of their
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
The value of chemical peaks depends upon the chemical environment around the hydrogen atom.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)
When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3Hdoublet, a 6H doublet, and two 1H multiplets. The 1H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identifycompounds A and B.
Compound X (molecular formula C10H120) was treated with NH2NH2, ¯OH to yield compound Y (molecular formula C10H14). Match
the 1H NMR spectra of X and Y to the corresponding structures of X and Y.
Compound NH2NH2 Compound
'H NMR of X
6 H
OH
Y
1 H
5H
8.
6.
4
ppm
or
H NMR of Y
6 H
2H
5H
1 H
multiplet
multiplet
8.
6.
4.
3.
1
nnm
2.
2.
3,
O:
Chapter 19 Solutions
Organic Chemistry - Standalone book
Ch. 19.1 - Prob. 1PCh. 19.4 - Prob. 2PCh. 19.5 - Prob. 3PCh. 19.6 - Problem 19.6 What is the most acidic neutral...Ch. 19.7 - Problem 19.6 Write an ionic equation for the...Ch. 19.9 - Prob. 6PCh. 19.11 - Prob. 7PCh. 19.12 - Prob. 8PCh. 19.14 - Prob. 9PCh. 19.15 - Prob. 10P
Ch. 19.16 - Prob. 11PCh. 19.16 - Prob. 12PCh. 19 - Prob. 13PCh. 19 - Prob. 14PCh. 19 - Prob. 15PCh. 19 - Prob. 16PCh. 19 - Show how butanoic acid may be converted to each of...Ch. 19 - Show by a series of equations how could synthesize...Ch. 19 - Prob. 19PCh. 19 - Prob. 20PCh. 19 - Prob. 21PCh. 19 - Give the product of the reaction of pentanoic acid...Ch. 19 - Prob. 23PCh. 19 - Prob. 24PCh. 19 - Each of the follwing reactions has been reported...Ch. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - Prob. 28PCh. 19 - Prob. 29PCh. 19 - Prob. 30PCh. 19 - The 1H NMR spectra of formic acid (HCO2H), maleic...Ch. 19 - Prob. 32PCh. 19 - Prob. 33PCh. 19 - Prob. 34DSPCh. 19 - Prob. 35DSPCh. 19 - Lactonization Methods In Section we saw that...Ch. 19 - Prob. 37DSP
Knowledge Booster
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
- Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.arrow_forwardCompound 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_forwardThe 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forward
- Compound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows…arrow_forwardCompound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning.arrow_forward
- An unknown compound has a molecular formula of C,H,O. Its IR spectrum shows prominent absorptions at 2980, 2960, and 1718 cm . It exhibits the following signals in its H NMR spectrum (ppm): 1.06 (triplet, 3H), 2.12 (singlet, 3H), 2.45 (quartet, 2H); and the following signals in its ¹3C NMR spectrum ( ppm): 7.6, 29.5, 36.8, 208.8. Draw the structure of the unknown compound. Click and drag to start drawing a structure. 0 X 0:0arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.25 ppm and two doublets, one at 7.28 ppm and one at 7.39 ppm. The singlet has an integral of three and the doublets each have an integral of two. The mass spectrum of A shows a peak at m/z = 126 and another peak at m/z = 128; the relative height of the two peaks is 3:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoningarrow_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forward
- A and B are isomeric dicarbonyl compounds of the molecular formula C5H&O2. The 'H NMR spectrum of A contains a singlet at 2.05 ppm and another singlet at 5.40 ppm. The 'H NMR spectrum of B contains three signals: a singlet at 2.3 ppm, a triplet at 1.10 ppm and a quartet at 2.70 ppm. Suggest structures for A and B and draw them in their respective boxes below. 1st attemptarrow_forwardAn unknown compound C of molecular formula C6H12O32 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of 1H NMR spectrum. What is the structure of C?arrow_forwardIsomer set #1: CH3OCCH,CH3 CH3COCH,CH3 a b Compound D, CHgO2, shows a downfield singlet in its 'H-NMR spectrum. Is it compound a or b? Isomer set #2: CH3OCCH2CH3 CH3COCH2CH3 a b. Compound D, C,H8O2, shows a downficld quartet in its 'H-NMR spectrum. Is it compound a or b?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY