Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 14, Problem 14.42AP
Interpretation Introduction
(a)
Interpretation:
The compound is to be identified from its IR and proton NMR spectra.
Concept introduction:
The NMR stands for nuclear magnetic resonance. NMR spectroscopy deals with the interaction between
Interpretation Introduction
(b)
Interpretation:
The compound is to be identified from their IR and proton NMR spectra.
Concept introduction:
The NMR stands for nuclear magnetic resonance. NMR spectroscopy deals with the interaction between electromagnetic radiation and the nucleus of an atom. NMR spectroscopy is used to determine the structural information about compounds.
Interpretation Introduction
(c)
Interpretation:
The compound is to be identified from their IR and proton NMR spectra.
Concept introduction:
The NMR stands for nuclear magnetic resonance. NMR spectroscopy deals with the interaction between electromagnetic radiation and the nucleus of an atom. NMR spectroscopy is used to determine the structural information about compounds.
Interpretation Introduction
(d)
Interpretation:
The compound is to be identified from their IR and proton NMR spectra.
Concept introduction:
The NMR stands for nuclear magnetic resonance. NMR spectroscopy deals with the interaction between electromagnetic radiation and the nucleus of an atom. NMR spectroscopy is used to determine the structural information about compounds.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The 1H-NMR spectrum of Compound D of molecular formula C10H12O shows three singlets – δ 2.20 (6H, s), 4.86 (4H), 7.10 (2H) ppm. Its 13C-NMR spectrum has five signals – 20, 74, 127, 135, 146 ppm. Suggest a structure for this compound.
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)
A compound with molecular formula
C7H1402 upon hydrolysis produces an
alcohol and an acid. It has the following
(b)
NMR data :
'H-NMR (at 298 K, 600 MHz, CDC13) :
80-92 (d, 6H), 1:52 (т, 2н), 1-69
(m, 1Н), 2-04 (s, ЗH) and 4-09 (t, 2H).
13 C-NMR :
8 21-0, 22:5, 25:1, 37.4, 63·1 and
171-2 ppm
DEPT provided two inverted signals.
Predict the structure of the alcohol that
is obtained through hydrolysis of the
mentioned parent compound. Assign
appropriate IR values, 'H and 13C-NMR
resonances along with a mass spectral
pattern for the alcohol.
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - Prob. 14.1PCh. 14 - Prob. 14.2PCh. 14 - Prob. 14.3PCh. 14 - Prob. 14.4PCh. 14 - Prob. 14.5PCh. 14 - Prob. 14.6PCh. 14 - Prob. 14.7PCh. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Prob. 14.11PCh. 14 - Prob. 14.12PCh. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - Prob. 14.15PCh. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - Prob. 14.20PCh. 14 - Prob. 14.21PCh. 14 - Prob. 14.22PCh. 14 - Prob. 14.23PCh. 14 - Prob. 14.24PCh. 14 - Prob. 14.25PCh. 14 - Prob. 14.26APCh. 14 - Prob. 14.27APCh. 14 - Prob. 14.28APCh. 14 - Prob. 14.29APCh. 14 - Prob. 14.30APCh. 14 - Prob. 14.31APCh. 14 - Prob. 14.32APCh. 14 - Prob. 14.33APCh. 14 - Prob. 14.34APCh. 14 - Prob. 14.35APCh. 14 - Prob. 14.36APCh. 14 - Prob. 14.37APCh. 14 - Prob. 14.38APCh. 14 - Prob. 14.39APCh. 14 - Prob. 14.40APCh. 14 - Prob. 14.41APCh. 14 - Prob. 14.42APCh. 14 - Prob. 14.43APCh. 14 - Prob. 14.44APCh. 14 - Prob. 14.45APCh. 14 - Prob. 14.46APCh. 14 - Prob. 14.47AP
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 H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_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
- Propose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. Compound C: IR absorption at 1717 cm-1arrow_forwardAn unknown compound A has the molecular formula C4H8O2. Based on the following 1H NMR spectrum, what is the structure of compound A?arrow_forwardCompound A has a molecular formula C5H11NO and a HNMR spectrum as such: 8.05 (s, 1H), 3.04 (s, 3H), 2.67 (t, 2H), 1.55 (m, 2H), 0.91 (t, 3H). The CNMR shows one peak above 160ppm. When hydrolyzed with H3O+, two compounds are formed B and C after aqueous workup. Draw the structures of A, B, and C.arrow_forward
- Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.arrow_forward1 (a) In the following reactions, CI (1) LIAIH, A (2) H20 MCPBA (i) Draw the structure of compounds A and B. (ii) For each reaction, explain the type of reaction involved. (iii) Explain the successful transformation of compound A using mass spectra. (b) Complete the following reactions by filling in missing reactants or product. (i) (1) O3 (2) CH;SCH3 (ii) он (CH3)3(COOH) D Ti(OCH(CH3)2l4 (-)-DETarrow_forwardWhen 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.arrow_forward
- 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 3H doublet, 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. Identify compounds A and B.arrow_forwardAcid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in its IR spectrum at 1770 cm-1 and the following signals in its 1H NMR spectrum: 1.27 (singlet, 6 H), 2.12 (triplet, 2 H), and 4.26 (triplet, 2 H) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.arrow_forwardPropose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. Compound C: IR absorption at 1717 cm–1arrow_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