Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 9, Problem 13PP
PRACTICE PROBLEM 9.13
How many signals would you expect to obtain in the
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Give the structure for two isomers of molecular formula C4H10O which are consistent with the ^1H-NMR spectra shown below.
The 1HNMR signals the alkene protons of three ethylene derivatives with different substitution patterns are shown below.
Considering that each of the derivatives contains AT MOST two substituents (X and/or Y) and at least two protons.
A) Propose the possible substitution patterns for each of the derivatives based on the observed splitting patterns. Justify your proposals
B) How might one differentiate between the three possible isomers of derivative 3 in the question above using 1H NMR spectroscopy? Explain in a sentence – no calculation is needed.
C) Give TWO methods that can be used to differentiate between the three possible isomers of derivative 2 in the question above using 1H NMR spectroscopy? Explain in a sentence – no calculation is needed.
For each problem, you must:1) Calculate the degree of unsaturation.2) Assign the principal IR absorption bands above 1500 cm -13) Draw the structure of the compound4) Label the protons on your structure with letters and assign them to peaks on the NMR spectrum(see the example below)
Chapter 9 Solutions
Organic Chemistry
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...
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- Discuss the similarities and difference you expect to see in their FT-IR spectra by going from compound 1 to 2arrow_forwardDeduce and draw the high-resolution 1H NMR spectrum of propan-1-ol and explain why two triplets at different chemical shifts are observed in this spectrum.arrow_forwardIdentify the structure of the compound a with a formula of C3H6O2 having the following IR, and 1H NMR spectra (integrals and multiplicity shown in the boxes: s-singlet, d-doublet, t-triplet, q-quartet, etc.). Label the spectra with proper information you deduced (functional groups, number of protons, fragments, etc.). Compound formula. C3H6O2 Questions to help you decide What is the element of unsaturation of the molecular formula? Show the equation you use: What are the functional groups present in this molecule? Show all of them belowDraw at least two possible structures that have the . required element of unsaturation as well as the observed functional groups: Based on the 1H NMR above, what molecular fragmentations do you see: Draw your final decision of the structure below. Is this one of the structures in your answer 5C?arrow_forward
- What information can be obtained from the UV-visible spectrum for compound 1 and 2?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_forwardPropose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.) a. The 1H NMR spectrum of a compound with molecular formula C4H10O2 has two singlets with integral ratios of 2 : 3. b. The 1H NMR spectrum of a compound with molecular formula C6H10O2 has two singlets with integral ratios of 2 : 3. c. The 1H NMR spectrum of a compound with molecular formula C8H6O2 has two singlets with integral ratios of 1 : 2.arrow_forward
- Predict 1H NMR (with splitting patterns) and 13C NMR chemical shifts for the benzene Alkene derivative below .arrow_forwardplease help with this question. thank you. Deduce the identity of the following compound from the 1H NMR data given and briefly explain.arrow_forwardReaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane (CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm−1. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.arrow_forward
- Define the Characteristic Spectroscopic Absorptions of BenzeneDerivative ?arrow_forwardFor the following compound: C3H5BrO2 (Molecular Weight = 152) -Calculate the degrees of unsaturation -Use the IR and NMR to determine the structure for your compound -All 1H NMR peaks (number of signals, chemical shift, integration and splitting)-All 13C NMR peaks (number of signals and chemical shift)-All IR peaks that are important (no need to look into the fingerprint region!)-Your proposed structure of the compound (C3H5BrO2) and how it matches with the spectra (images attached)arrow_forwardcompound with the molecular formula C7H9N exhibits IR bands at 3450 cm-1 (medium, doublet), and 855 cm-1 (strong) and shows the following major mass spectral signals (m/z): 106 (base); 107 (M+, about 70% of base), 91 (40% of base), and 77 (about 20% of base). Deduce a reasonable structure from this data.arrow_forward
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