Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 13.14, Problem 23P
Interpretation Introduction
Interpretation:
The absorption occurred at larger wavenumber, the carbonyl group bonded to
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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
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.
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
Chapter 13 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 13.1 - Which of the following fragments produced in a...Ch. 13.2 - What distinguishes the mass spectrum of...Ch. 13.2 - What is the most likely m/z value for the base...Ch. 13.3 - Prob. 5PCh. 13.3 - a. Suggest possible molecular formulas for a...Ch. 13.3 - If a compound has a molecular ion with an...Ch. 13.3 - Identify the hydrocarbon that has a molecular ion...Ch. 13.4 - Predict the relative intensities of the molecular...Ch. 13.5 - Which molecular formula has an exact molecular...Ch. 13.5 - Prob. 11P
Ch. 13.6 - Sketch the mass spectrum expected for...Ch. 13.6 - The mass spectra of 1-methoxybutane,...Ch. 13.6 - Primary alcohols have a strong peak at m/z = 31....Ch. 13.6 - Identify the ketones responsible for the mass...Ch. 13.6 - Prob. 16PCh. 13.6 - Using curved arrows, show the principal fragments...Ch. 13.6 - The reaction of (Z)-2-pentene with water and a...Ch. 13.9 - a. Which is higher in energy: electromagnetic...Ch. 13.9 - Prob. 20PCh. 13.13 - Prob. 21PCh. 13.14 - Which occur at a larger wavenumber: a. the C O...Ch. 13.14 - Prob. 23PCh. 13.14 - Prob. 24PCh. 13.14 - Rank the following compounds from highest...Ch. 13.14 - Which shows an O H stretch at a larger...Ch. 13.16 - Prob. 27PCh. 13.16 - a. An oxygen-containing compound shows an...Ch. 13.16 - Prob. 29PCh. 13.16 - For each of the following pair of compounds, name...Ch. 13.17 - Which of the following compounds has a vibration...Ch. 13.17 - Prob. 32PCh. 13.18 - A compound with molecular formula C4H6O gives the...Ch. 13.20 - Prob. 34PCh. 13.20 - Prob. 35PCh. 13.21 - Predict the max of the following compound:Ch. 13.21 - Prob. 37PCh. 13.23 - a. At pH = 7 one of the ions shown here is purple...Ch. 13.23 - Prob. 39PCh. 13.23 - Prob. 40PCh. 13 - In the mass spectrum of the following compounds,...Ch. 13 - Prob. 42PCh. 13 - Draw structures for a saturated hydrocarbon that...Ch. 13 - Rank the following compounds in order of...Ch. 13 - For each of the following pairs of compounds,...Ch. 13 - a. How could you use IR spectroscopy to determine...Ch. 13 - Assuming that the force constant is approximately...Ch. 13 - Norlutin and Enovid are ketones that suppress so...Ch. 13 - In the following boxes, list the types of bonds...Ch. 13 - A mass spectrum shows significant peaks at m/z. =...Ch. 13 - Prob. 51PCh. 13 - Prob. 52PCh. 13 - Prob. 53PCh. 13 - The IR spectrum of a compound with molecular...Ch. 13 - Rank the following compounds from highest...Ch. 13 - Rank the following compounds from highest...Ch. 13 - What peaks in their mass spectra can be used to...Ch. 13 - Prob. 58PCh. 13 - Which one of the following five compounds produced...Ch. 13 - Prob. 60PCh. 13 - Each of the IR spectra shown below is accompanied...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - How can IR spectroscopy distinguish between...Ch. 13 - Prob. 65PCh. 13 - Prob. 66PCh. 13 - Give approximate wavenumbers for the major...Ch. 13 - Prob. 68PCh. 13 - Which one of the following live compounds produced...Ch. 13 - Phenolphthalein is an acid-base indicator. In...Ch. 13 - Prob. 71PCh. 13 - How can you use UV spectroscopy to distinguish...Ch. 13 - Prob. 73PCh. 13 - The IR and mass spectra for three different...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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)arrow_forwardIn 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_forwardWhich shows an O¬H stretch at a larger wavenumber: ethanol dissolved in carbon disulfide or an undiluted sample of ethanol?arrow_forward
- Match 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_forwardWhat is the R/S configuration of the indicated toms of the following molecule?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
- 2. 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_forwardWhen 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_forward
- What 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_forwardChoose 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_forwardSignal b in the spectrum for 2-ethoxyethyl acetate ( comes from the Hs connected to: O C4 C1 C3 O C2 O C5 PPM G11C2 CA C5arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY