Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 12, Problem 38P
An unknown X shows a broad absorption band in the infrared at 3200-3550
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Draw the structure of the important peaks in the mass spectrum of C9H8O (unsaturation = 6)
Major Peaks:
m/z = 132, 103, 77, 53
Identify and explain the IR absorption characteristics of the unknown C6H14O in the 1400 to 4000 cm-1 range. Then identify the class of the unknown compound C6H14O.
At the broad peak I believe it is either an alcohol & phenol or an amine. For the second peak i think it is an alkane.
3. Identify C-Cl stretching peaks in CDC13 and CHC13 spectra. Do these peaks
have exactly the same frequencies for both compounds? Explain your answer.
4. Is the C==O stretching frequency the same for acetone and deuterated acetone?
Explain your answer.
5. Identify C==O overtone in acetone spectrum which corresponds to the transition
from ground level, n=0, to the second excited level, n=2.
Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 1PPCh. 12 - Prob. 2PPCh. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 5PPCh. 12 - Prob. 6PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 8PPCh. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...
Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 12PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 14PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 20PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 22PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 24PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 27PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Predict the major organic product from each of the...Ch. 12 - 34. Synthesize the following compound using...Ch. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 39PCh. 12 - The problem below is directed toward devising a...
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- The spectra (IR, 'H NMR, ®C NMR and MS) of an unknown compound are shown in the following spetra. Based on these spectra, determine the structure of the unknown compound. Explain your answers clearly for each spectrum. Ahserbance / IR 2000 Wavenumbers /em 13C NMR 130-128 14 61 145 22 167 160 140 120 200 180 100 PPm 80 60 40 20arrow_forwardThe infrared absorption spectrum of 12C14N has its strongest band at 2500 cm-1 wavenumber. Calculate the force constant (N/m) of the bond in this molecule.arrow_forwardThe IR spectra of nonane (C,H20) and 1-hexanol (C,H13OH) are shown below. Assign each spectrum to the correct compound and identify the frequencies and the functional groups used to support your assignment. λ (μη) 6 7 8 9 10 11 12 1314 15 2.5 100 3 5 20 4 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬') A (µm) 2.5 100 8 9 10 11 12 13 14 15 3 4 5 7 20 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬!) (%) Transmission (%) Transmissionarrow_forward
- Which molecule has the IR spectrum below. A B C D Transmitance 0.8 0.6 0.4 0.2 4000 OH A 3000 B INFRARED SPECTRUM 2000 Wavenumber (cm-1) OH с 1000 H NH₂ Darrow_forwardG Some absorptions may be weak but can be identified. Consider 4-tert-butylbenzonitrile and locate the four absorptions on the spectrum as each corresponds to the molecular bond. %T 100 80 60 40 20 2000 3000 CEN 2000 CC 1500 Wavenumberlcm-1] 1000 500 400 Identify these absorptions: C=N sp² C-H sp³ C-H C=C 2 EN ✓ 1arrow_forwardA low-resolution mass spectrum of the neurotransmitter dopamine gave a molecular ion at m/z = 153. Two possible molecular formulas for this molecular ion are C8H11NO2 and C7H11N3O. A high-resolution mass spectrum provided an exact mass at 153.0680. Which of the possible molecular formulas is the correct one?arrow_forward
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