Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 10.13, Problem 18P
Interpretation Introduction
Interpretation:
The absorption occurred at larger wavenumber, the carbonyl group bonded to
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Identify the frequency of both carbonyl stretches in your IR. Which one corresponds to the benzyl ester?
Wavenumber (cm-1)
Bond
Vibration
Shape
Intensity
Functional Group
3288.63 cm-1
N-H
Stretch
Sharp
Weak
Amine/Amide
3078.39 cm-1
C-H
Stretch
Sharp
Weak
Aromatic/Alkene
2976.16 cm-1
C-H
Stretch
Sharp
Weak
Alkane
1720.50 cm-1
C=O
Stretch
Sharp
Medium
Ester
1653.00 cm-1
C=O
Stretch
Sharp
Medium
Amide
1556.55 cm-1
C=C
Stretch
Sharp
Medium
Aromatic
Which of the following is not true regarding infrared spectroscopy?
wavenumbers units are inverse centimeters (cm-¹)
a stronger bond will have a higher wavenumber stretch
conjugated carbonyls have a lower wavenumber stretch
A larger bond dipole will lead to a lower intensity IR absorption
Which shows an O¬H stretch at a larger wavenumber: ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?
Chapter 10 Solutions
Essential Organic Chemistry, Global Edition
Ch. 10.1 - Prob. 1PCh. 10.2 - What would distinguish the mass spectrum of...Ch. 10.2 - Prob. 3PCh. 10.3 - Prob. 5PCh. 10.3 - Suggest possible molecular formulas for a compound...Ch. 10.3 - Prob. 7PCh. 10.4 - Prob. 8PCh. 10.4 - Prob. 9PCh. 10.5 - Prob. 10PCh. 10.5 - Prob. 11P
Ch. 10.6 - Identify the ketone responsible for the mass...Ch. 10.6 - Prob. 13PCh. 10.8 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10.12 - Which will occur at a larger wavenumber: a. a C :...Ch. 10.13 - Which will occur at a larger wavenumber: a. the C...Ch. 10.13 - Prob. 18PCh. 10.13 - Prob. 19PCh. 10.13 - Which will show an O 8 H stretch at a larger...Ch. 10.14 - Prob. 21PCh. 10.14 - Prob. 22PCh. 10.15 - Prob. 23PCh. 10.15 - Prob. 24PCh. 10.17 - Prob. 25PCh. 10.18 - Prob. 26PCh. 10.18 - Prob. 27PCh. 10.19 - Prob. 28PCh. 10.19 - Prob. 29PCh. 10.22 - How many signals would you expect to see in the 1H...Ch. 10.22 - Prob. 31PCh. 10.22 - Prob. 32PCh. 10.23 - Where would you expect to find the 1H NMR signal...Ch. 10.24 - Prob. 34PCh. 10.25 - Prob. 35PCh. 10.25 - Prob. 36PCh. 10.25 - Prob. 37PCh. 10.26 - Prob. 38PCh. 10.26 - Which of the following compounds is responsible...Ch. 10.27 - Prob. 40PCh. 10.27 - Prob. 41PCh. 10.27 - The 1H NMR spectra of two carboxylic acids with...Ch. 10.28 - Prob. 43PCh. 10.28 - Prob. 44PCh. 10.28 - Prob. 45PCh. 10.28 - Describe the 1H NMR spectrum you would expect for...Ch. 10.28 - Identify the compound with molecular formula...Ch. 10.29 - Prob. 48PCh. 10.29 - Prob. 49PCh. 10.29 - Identify the compound with a molecular formula of...Ch. 10 - In the mass spectrum of the following compounds,...Ch. 10 - For each of the following pairs of compounds,...Ch. 10 - Draw the structure of a saturated hydrocarbon that...Ch. 10 - Prob. 54PCh. 10 - Prob. 55PCh. 10 - How could you use UV spectroscopy to distinguish...Ch. 10 - Prob. 57PCh. 10 - Predict the relative intensities of the molecular...Ch. 10 - Prob. 59PCh. 10 - List the following compounds in order from highest...Ch. 10 - How can 1H NMR be used to prove that the addition...Ch. 10 - There are four esters with molecular formula...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - Each of the IR spectra presented here is...Ch. 10 - Prob. 66PCh. 10 - Five compounds are shown for each of the following...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Phenolphthalein is an acidbase indicator. In...Ch. 10 - Which one of the following five compounds produced...Ch. 10 - Prob. 72PCh. 10 - Prob. 73PCh. 10 - Prob. 74PCh. 10 - How could 1H NMR distinguish between the compounds...Ch. 10 - Prob. 76PCh. 10 - Prob. 77PCh. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - Identify the following compounds. (Relative...Ch. 10 - An alkyl halide reacts with an alkoxide ion to...Ch. 10 - Determine the structure of a compound with...
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- In an IR spectrum, the C-0 stretch for an alcohol (ROH) or an ether (ROR) appears near 1050 cm¯1, but for a carboxylic acid (RCO,H) or an ester (RCO,R), the C-0 stretch appears near 1250 cm-1. Explain why. -1050 cm-1 -1050 cm-1 -1250 cm-1 -1250 cm-1 R R R Rarrow_forwardPlease don't provide handwriting solutionarrow_forward2. Both the compounds shown below contain a carbonyl group but there is slight variation in the wavenumber of the peak as shown below. h f 1720 cm-1 1680 cm-1 Explain the possible reason of this variation.arrow_forward
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- Choose the best explanation for why -OH and -NH peaks are often broad singlets in a ¹H NMR spectrum. A) The greater electronegativity difference in the N-H or O-H bond compared to a C-H bond makes the peak broader. B) The greater mass involved in the N-H or O-H bond compared to a C-H bond makes the peak broader. C) The hydrogen nuclei on the carbon next to the -OH or -NH are too far away to impact the multiplicity. D) Protons in OH or NH groups are acidic enough to rapidly exchange between different molecules, so the coupling to vicinal hydrogens is not clearly observed.arrow_forwardWhat are the peaks and chemical shifts in this H NMR? What is the major product and minor product in the H NMR (between 1-methylcyclohexene and 3-methylcyclohexene)? What was the percentage od the major and minor products in the product picture (which is the H NMR)? This is like the ratio between 1-methylcyclohexene and 3-methylcyclohexene.arrow_forwardGiven is the mass spectra of n-octane whre peaks are labeled accordingly. Give the letter that corresponds to the peak described below:arrow_forward
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