Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 14, Problem 37P
Explain why the cyclopentadienide anion A gives only one signal in its 13C NMR spectrum.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1
H NMR spectrum of compound A has a 1H singlet, a 3H
doublet, a 6H doublet, and two 1H multiplets. The 1
H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify
compounds A and B.
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.
An unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of C?
Chapter 14 Solutions
Organic Chemistry (6th Edition)
Ch. 14.1 - Prob. 2PCh. 14.2 - Problem 16.3 Draw a second resonance structure for...Ch. 14.2 - Prob. 4PCh. 14.2 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 14.3 - Prob. 6PCh. 14.4 - Prob. 7PCh. 14.4 - Prob. 8PCh. 14.8 - Problem 16.12 Using hybridization, predict how the...Ch. 14.8 - Problem 16.13 Use resonance theory to explain why...Ch. 14.9 - Prob. 15P
Ch. 14.9 - Prob. 16PCh. 14.10 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 14.11 - Prob. 19PCh. 14.12 - Problem 16.19 Draw the product formed when each...Ch. 14 - Prob. 32PCh. 14 - 16.31 Which of the following systems are...Ch. 14 - 16.32 Draw all reasonable resonance structures for...Ch. 14 - Prob. 35PCh. 14 - 16.35 Explain why the cyclopentadienide anion A...Ch. 14 - Prob. 38PCh. 14 - 16.37 Draw the structure of each compound.
a. in...Ch. 14 - 16.41 Draw the products formed when each compound...Ch. 14 - Prob. 44PCh. 14 - 16.43 Treatment of alkenes A and B with gives the...Ch. 14 - 16.44 Draw a stepwise mechanism for the following...Ch. 14 - Prob. 47PCh. 14 - 16.57 A transannular Diels–Alder reaction is an...Ch. 14 - Draw a stepwise mechanism for the following...Ch. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - 16.65 The treatment of isoprene with one...
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
- When diphenyl ether is reacted under the same conditions as in Problem 22.35, a compound is produced whose 13C NMR spectrum shows six signals. Draw that product.arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?arrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forward
- Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2),which has an IR absorption at 1699 cm−1 and the 1H NMR spectrumshown below.arrow_forwardA compound with molecular formula C5H10Br2 displays the following 13C NMR along with the DEPT-90 and DEPT-135 13CNMR spectra. What is the structure for this compound?arrow_forward
- The compound with the 1H NMR spectrum shown is known to be highly reactive toward electrophilic aromatic substitution. Identify the compound.arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forward
- When treated with an equivalent of methanol, compound A, with molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.arrow_forwardIdentify the structure of compound A (molecular formula C9H10O) from the 1H NMR and IR spectra given.arrow_forwardAll-cis cyclodecapentaene is a stable molecule that shows a single absorption in its1HNMR spectrum at 5.67 δ. Tell whether it is aromatic, and explain its NMR spectrumarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY