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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Students have asked these similar questions
Why do aldehydes, esters, and amides all have a strong absorption in the
1630-1780 cm1 region of their IR spectra?
A) The bond between H and the sp³-hybridized C in these functional groups
vibrates in this energy range.
B) Each of these functional groups has at least two resonance structures, and
the different vibrations of the resonance structures give off energy in this
region.
C) The bond between O and the sp²-hybridized C in these functional groups
vibrates at a frequency in this energy range.
D) Light at this wavenumber causes the average C to O bond length to increase
which causes more of this light to be transmitted.
E) An electron in the bond of these functional groups gets excited to the *
orbital.
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
Match the appropriate wavenumber where you would find the following functional groups in an IR spectrum.
CH stretch (sp², aromatic)
1. 1700 cm1
C-H stretch (sp, aliphatic)
2. -3500 cm 1
C=0 stretch
3. 3200-2800 cm1
4. 3150-3050 cm
O-H stretch (carboxylic acid)
5. 2950-2850 cm
O-H stretch (phenol)
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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- 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 absorptionarrow_forwardWhich shows an O¬H stretch at a larger wavenumber: ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?arrow_forwardMatch the appropriate wavenumber where you would find the following functional groups in an IR spectrum. C-H stretch (sp³, aliphatic) 1. ~1700 cm-1 C=O stretch 2. ~3500 cm-1 O-H stretch (carboxylic acid) 3. ~3200-2800 cm 4. ~3150-3050 cm C-H stretch (sp², aromatic) 5. ~2950-2850 cm O-H stretch (phenol)arrow_forward
- 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_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_forwardWhat is the R/S configuration of the indicated toms of the following molecule?arrow_forward
- When the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols? (a) 2-Methyl-2-propanol (b) Cyclohexanol (c) Ethanol (d) 2-Propanol (e) Cholesterol (f) 1-Methylcyclohexanolarrow_forwardWould you expect two enantiomers such as (R)-2-bromobutane and (S)-2-bromobutane to have identical or different IR spectra? Explain.arrow_forwardWhich of the following has an IR carbonyl stretch at a higher wavenumber? 1 1 O 2 f2 f3 f4 fs f6 fe 7 & 5 Q W R T 图 # Marrow_forward
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