ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 9, Problem 24P
Interpretation Introduction
Interpretation:
The structures for O and P are to be proposed on the basis of the given information.
Concept introduction:
In NMR, the chemical shift of the nucleus depends on the relative electron density around an atom. Attached with highly electronegative atoms means highly deshielded and higher will be the chemical shift value.
DEPT
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Provide a structure for the compound C,H1,N, using the given information.
IR: 3281 cm-1
'H NMR: 8 1.1 (8H, t, J = 7 Hz), 8 2.66 (4H, q, J = 7 Hz), 8 2.83 (4H, s). (Hint: The triplet at & 1.1 conceals another
broad resonance that contributes to the integral.)
9.
Compound A is treated with HONO,
followed by a reaction with Compound B; the
final product obtained is shown below. H NMR
spectra for Compounds A and B are provided.
(a) Provide structures of Compounds A and B in
the boxes below.
(b) Label the signals on each spectrum with letters
(as outlined on Week 3 Tuesday slide 4), then
assign all H NMR signals to specific chemical
environments or specific protons on the
structures of Compounds A and B.
Compound
CompoundA
HONO
Fr Product
H NMR Compound A
2H
1H
1H 1H 1H
3H
H NMR Compound B
2H
1H
1H
2H
10)Pyrrolium (1) and pyridinium (2) have markedly H
different pK, values. Circle the compound with the lower
pK₂ value.
-N-H
11) The 1H NMR spectrum of phenol is shown below. Of note, the aryl proton signals
resolve in this molecule. Assign protons to specific signals in the spectrum
8
7
6
H₂
H₁
5 ppm
H3
H₂
*CHCl3
2
H₁
Chapter 9 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
Knowledge Booster
Similar questions
- If this NMR is of a low molecular weight ether, propose a possible structure.arrow_forwardWhat is the 1H NMR data (chemical shift, integration, mulitplicity) of the compound shown below? Clearly label all hydrogens that are being reported.arrow_forwardPropose a structure for compounds A and B whose spectra are shown. How do you do this problem step-by-step thank youarrow_forward
- Propose a structure consistent with each set of data. molecular ion at 72; IR peak at 1710 cm−1; 1H NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4(quartet, 2 H)arrow_forwardUsing 'H NMR Spectroscopy to Distinguish between Compounds Provide a structure that is consistent with the data below. C7H160 IR (cm 1): 3200-3600 (broad), 2950 H NMR ( delta, ppm): 2.8 (1H, broad s), 1.4 (6H, s), 0.9 (9H, s) HO, OH C OB Oc OAarrow_forwardwhat is the structure of the major product with protons labeled, along with a table that lists those protons chemical shift (d, ppm), integration, multiplicity, and J-values (Hz). Note – your aromatic signals will have to be listed as multiplets, and will need a chemical shift range. e.g. 7.58-7.30 (m, 5H)arrow_forward
- Which structure with molecular formula C1H160 matches the IH NMR shown? The boxes are zoomed portions of the spectra. (d) (t) (quintet) (sextet) 2H2H 3H 1H 2H 3H 3Harrow_forwardFor each structure given, predict the number of proton signals that will be observed in the 1H NMR spectrum an predict their multiplicity (e.g. singlet, douplet, etc.)arrow_forwardPlease show complete answer. Propose a structure consistent with following set of spectral data: a. C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H) b. C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)arrow_forward
- Provide a structure that is consistent with the data below. C7H160 IR (cm-1): 3200-3600 (broad), 2950 1H NMR (d): 2.8 (1H, broad s), 1.0 (6H, s), 0.9 (9H, s) 13C NMR (d): 68 (s), 39 (s), 16 (q), 13 (q)arrow_forwardDraw the structure with formula C5H12O2 that fits the following NMR spectrumarrow_forwardThere are four isomers shown below (compounds A-D). TWO of these isomeric nitrogen- containing compounds were extracted and isolated from tobacco leaves. Their structures were determined using 1H NMR. These two 1H NMR spectra are shown below. Make peak assignments of the NON-AROMATIC signals to determine which TWO isomers are represented. Use the specific labels (a-h) provided with spectra.arrow_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