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 40P
Interpretation Introduction
Interpretation:
The structure of the compound that gives the spectra
Concept introduction:
Mass spectrometry is a technique used for measuring the masses of atoms and molecules with accuracy.
In a mass spectrometer, the vapor of an organic compound is bombarded with a beam of high-energy electrons that makes the neutral molecule lose an electron and converts it into a radical cation, which is known as a molecular ion. With the help of 13 C NMR the types of carbon atom can be determined and the IR spectroscopy can be used in detecting the
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Below are the spectral data (IR, MS, 1H NMR, and 13C NMR) for an unknown organic compound. Examine the data carefully and answer the questions that follow.3a) What functional group do you observe in the IR spectrum? 3b)How may signals from sp3 carbons in 13C-NMR
3c)How many signals sp2 carbons in 13C-NMR
3d) What is the formula of this molecule (you may need to solve structure first)? 3e) Proposed structure
Predict the structure of the compound using the information below. Kindly show what information are obtained for each spectra which may help in predicting the structure.
From IR Spectra: See the attached picture
From Mass Spectra:
M+ = 216
peaks at 29 (base peak) and 188
From Proton and Carbon NMR Spectra: See attached picture.
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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- This CANNOT be hand-drawn. Please digitally draw/illustrate and type any explanations.arrow_forwardThe 1H-NMR spectrum of ethanol shows a triplet at 1.23 ppm, a singlet at 2.61 pm, and a quartet at 3.69 ppm. Assign each signal to the protons it corresponds to in the molecule. Explain the splitting pattern observed for each signal.arrow_forwardFollowing are the 'H and 13C NMR spectra for each of three isomeric ketones with formula C7H14O. Determine a structure to each pair of spectra and assign each H and C. Carbon spectrum B Carbon spectrum C,H140 А C,H140 CDCI3 CDCI3 200 150 100 50 200 150 100 50 Proton spectrum C,H140 В Proton spectrum A C,H140 2.9 2.8 2.7 1.96 2.00 2.91 1.04 6.18 3.0 2.5 2.0 1.5 1.0 0.5 0.0 3.0 2.5 2.0 1.5 0.5 0.0 211.04 -44.79 –17.39 – 13.78 -218.40 -38.85 –18.55arrow_forward
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