Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 21, Problem 21.49AP
Interpretation Introduction
Interpretation:
The structure of the compound A using given IR, NMR and reaction data is to be drawn.
Concept introduction:
The IR spectrum of a compound shows absorptions at different frequencies. These absorption frequencies depend upon the bond stretching frequency of the bonds in molecule.
The NMR spectrum of a molecule shows resonance at different levels. This is due to the protons’ position and their nature in molecule.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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
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)
Three compounds, A, B, and C, have the same molecular formula, C5H6. In the presence of a platinum catalyst, all three compounds absorb 3 molar equivalents of hydrogen and yield pentane. Compounds B and C give a precipitate when treated with ammoniacal silver nitrate; compound A give no reaction. Compounds A and B show an absorption maximum near 250 nm. Compound C shows no absorption maximum beyond 200 nm. Propose a structure for A, B, and C.
Chapter 21 Solutions
Organic Chemistry Study Guide and Solutions
Ch. 21 - Prob. 21.1PCh. 21 - Prob. 21.2PCh. 21 - Prob. 21.3PCh. 21 - Prob. 21.4PCh. 21 - Prob. 21.5PCh. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - Prob. 21.8PCh. 21 - Prob. 21.9PCh. 21 - Prob. 21.10P
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Prob. 21.15PCh. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Prob. 21.18PCh. 21 - Prob. 21.19PCh. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Prob. 21.22PCh. 21 - Prob. 21.23PCh. 21 - Prob. 21.24PCh. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Prob. 21.28PCh. 21 - Prob. 21.29PCh. 21 - Prob. 21.30PCh. 21 - Prob. 21.31PCh. 21 - Prob. 21.32APCh. 21 - Prob. 21.33APCh. 21 - Prob. 21.34APCh. 21 - Prob. 21.35APCh. 21 - Prob. 21.36APCh. 21 - Prob. 21.37APCh. 21 - Prob. 21.38APCh. 21 - Prob. 21.39APCh. 21 - Prob. 21.40APCh. 21 - Prob. 21.41APCh. 21 - Prob. 21.42APCh. 21 - Prob. 21.43APCh. 21 - Prob. 21.44APCh. 21 - Prob. 21.45APCh. 21 - Prob. 21.46APCh. 21 - Prob. 21.47APCh. 21 - Prob. 21.48APCh. 21 - Prob. 21.49APCh. 21 - Prob. 21.50APCh. 21 - Prob. 21.52APCh. 21 - Prob. 21.53APCh. 21 - Prob. 21.54APCh. 21 - Prob. 21.55APCh. 21 - Prob. 21.56APCh. 21 - Prob. 21.57APCh. 21 - Prob. 21.58APCh. 21 - Prob. 21.59APCh. 21 - Prob. 21.60APCh. 21 - Prob. 21.61APCh. 21 - Prob. 21.62APCh. 21 - Prob. 21.63AP
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
- 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_forwardPropose a structure for a compound of molecular formula C3H8O with an IR absorption at 3600–3200 cm−1 and the following NMR spectrum:arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forward
- As a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?arrow_forwardAn unknown compound A (molecular formula C7H14O) was treated with NaBH4 in CH3OH to form compound B (molecular formula C7H16O). Compound A has a strong absorption in its IR spectrum at 1716 cm−1. Compound B has a strong absorption in its IR spectrum at 3600−3200 cm−1. The 1H NMR spectra of A and B are given. What are the structures of A and B?arrow_forwardTreatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.arrow_forward
- Compound 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_forwardCompound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below. (a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum. (b) Based on the information provided, determine the structure of compound D.arrow_forwardA 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_forward
- A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?arrow_forwardTreatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?arrow_forwardCompound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.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
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY