Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Question
error_outline
This textbook solution is under construction.
Students have asked these similar questions
Propose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm−1 and the following 1H NMR data:
The 1H-NMR spectrum of compound R, C6H14O, consists of two signals: d 1.1 (doublet) and d 3.6 (septet) in the ratio 6:1. Propose a structural formula for compound R consistent with this information
The '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.
Knowledge Booster
Similar questions
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardAn unknown compound C3H2NCl shows moderately strong IR absorptions around 1650 cm-1 and 2200 cm-1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ 5.9 and δ 7.1. Propose a structure consistent with this data?arrow_forwardPropose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3arrow_forward
- Propose a structure for a compound of molecular formula C,H1402 with an IR absorption at 1740 cm and the following 'H NMR data: Absorption ppm Relative Area singlet 1.2 9 triplet 1.3 3 quartet 4.1arrow_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_forwardA 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_forward
- There are several isomeric alcohols and ethers of molecular formula C5H12O. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppm Isomer B: δ = 1.19 (s, 9 H), 3.21 (s, 3H) ppmarrow_forwardIdentify the compound with molecular formula C6H10O that gives the following DEPT 13C NMR spectrum:arrow_forwardA compound has a molecular formula of C8H8O The following spectra (1H NMR, Carbon 13 NMR, IR was collected. Give a possible structure. 13C NMR – 8 peaksarrow_forward
- The 1H-NMR spectrum of compound B,C7H14O , consists of the following signals: δ 0.9 (t, 6H), 1.6 (sextet, 4H), and 2.4 (t, 4H). Draw the structural formula of compound B.arrow_forwardPropose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm−1 and the following 1H NMR data: Absorption ppm Relative area singlet 1.2 9 triplet 1.3 3 quartet 4.1 2arrow_forwardIdentify the compound with molecular formula C6H14 that is responsible for the following 1H NMR spectrum: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