Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 15, Problem 15.26P
Interpretation Introduction
Interpretation:
The compounds
Concept introduction:
IR spectroscopy enables us to identify different
One of the greatest advantages of IR spectroscopy is that the frequency of a particular type of vibration is typically found within a characteristic range of frequencies, regardless of the functional group with which the vibration is associated. The fact that absorptions by certain vibrations appear with characteristic frequency ranges enables us to use IR spectroscopy to obtain structural information about a molecule. The absorption band for
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QUESTION 2
Predict the IR absorption bands (peaks) observed in the spectrum of isobutyl alcohol.
sp3 C-H stretching (-2850-2960 cm-1)
sp2 C-H stretching (-3000-3100 cm 1)
Alcohol O-H stretch (-3300 cm1, broad)
C-O double bond stretch (-1700 cm-1)
Aromatic out of plane bend for monosubstitution (690-710 and 730-770 cm-1).
Aromatic out of plane bend for para (1,4) disubstitution (810-840 cm-1).
Aromatic out of plane bend for meta (1,3) disubstitution (690-750 and 750-810 cm 1).
Aldehyde C-H stretch (2750 and 2850 cm-1).
Carboxylic acid (carboxy group) 0-H stretch (-2500-3000 cm-1, broad)
N-H stretch (2 bands at -3400 cm-1)
N-H bend (-1600 cm-1)
Aromatic C-C double bond stretches (-1500 and 1600 cm-1).
Aromatic overtones (1667-2000 cm
cm1)
O O
O O
O O O
Identify the important peaks in the following MS spectral data and draw the structure of the important peaks in the following MS spectral data.
Fill in the table by matching the numbers of the structure to their corresponding peaks of the C-13 spectra.
Chapter 15 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 15 - Prob. 15.1PCh. 15 - Prob. 15.2PCh. 15 - Prob. 15.3PCh. 15 - Prob. 15.4PCh. 15 - Prob. 15.5PCh. 15 - Prob. 15.6PCh. 15 - Prob. 15.7PCh. 15 - Prob. 15.8PCh. 15 - Prob. 15.9PCh. 15 - Prob. 15.10P
Ch. 15 - Prob. 15.11PCh. 15 - Prob. 15.12PCh. 15 - Prob. 15.13PCh. 15 - Prob. 15.14PCh. 15 - Prob. 15.15PCh. 15 - Prob. 15.16PCh. 15 - Prob. 15.17PCh. 15 - Prob. 15.18PCh. 15 - Prob. 15.19PCh. 15 - Prob. 15.20PCh. 15 - Prob. 15.21PCh. 15 - Prob. 15.22PCh. 15 - Prob. 15.23PCh. 15 - Prob. 15.24PCh. 15 - Prob. 15.25PCh. 15 - Prob. 15.26PCh. 15 - Prob. 15.27PCh. 15 - Prob. 15.28PCh. 15 - Prob. 15.29PCh. 15 - Prob. 15.30PCh. 15 - Prob. 15.31PCh. 15 - Prob. 15.32PCh. 15 - Prob. 15.33PCh. 15 - Prob. 15.34PCh. 15 - Prob. 15.35PCh. 15 - Prob. 15.36PCh. 15 - Prob. 15.37PCh. 15 - Prob. 15.38PCh. 15 - Prob. 15.39PCh. 15 - Prob. 15.40PCh. 15 - Prob. 15.41PCh. 15 - Prob. 15.42PCh. 15 - Prob. 15.43PCh. 15 - Prob. 15.44PCh. 15 - Prob. 15.45PCh. 15 - Prob. 15.46PCh. 15 - Prob. 15.47PCh. 15 - Prob. 15.48PCh. 15 - Prob. 15.49PCh. 15 - Prob. 15.50PCh. 15 - Prob. 15.51PCh. 15 - Prob. 15.52PCh. 15 - Prob. 15.53PCh. 15 - Prob. 15.54PCh. 15 - Prob. 15.55PCh. 15 - Prob. 15.56PCh. 15 - Prob. 15.57PCh. 15 - Prob. 15.58PCh. 15 - Prob. 15.59PCh. 15 - Prob. 15.60PCh. 15 - Prob. 15.61PCh. 15 - Prob. 15.62PCh. 15 - Prob. 15.63PCh. 15 - Prob. 15.64PCh. 15 - Prob. 15.65PCh. 15 - Prob. 15.66PCh. 15 - Prob. 15.67PCh. 15 - Prob. 15.68PCh. 15 - Prob. 15.1YTCh. 15 - Prob. 15.2YTCh. 15 - Prob. 15.3YTCh. 15 - Prob. 15.4YTCh. 15 - Prob. 15.5YTCh. 15 - Prob. 15.6YTCh. 15 - Prob. 15.7YTCh. 15 - Prob. 15.8YTCh. 15 - Prob. 15.9YTCh. 15 - Prob. 15.10YTCh. 15 - Prob. 15.11YTCh. 15 - Prob. 15.12YTCh. 15 - Prob. 15.13YTCh. 15 - Prob. 15.14YTCh. 15 - Prob. 15.15YTCh. 15 - Prob. 15.16YTCh. 15 - Prob. 15.17YTCh. 15 - Prob. 15.18YTCh. 15 - Prob. 15.19YTCh. 15 - Prob. 15.20YTCh. 15 - Prob. 15.21YTCh. 15 - Prob. 15.22YTCh. 15 - Prob. 15.23YTCh. 15 - Prob. 15.24YTCh. 15 - Prob. 15.25YTCh. 15 - Prob. 15.26YTCh. 15 - Prob. 15.27YTCh. 15 - Prob. 15.28YTCh. 15 - Prob. 15.29YTCh. 15 - Prob. 15.30YT
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- 3. Look at the two spectra below, one of which is 2-methylcyclohexanol and one of which is 3methylcyclohexene. Which spectrum belongs to which compound? Explain your reasoning. 10- 4000 200 3500 3000 2500 1500 1000 600 Spectrum A 90 20 30 20 10 500 3000 2500 2000 1600 1000 500 Vieters kn1 Spectrum Barrow_forwardIn the box provided, write the IR frequency or range of frequencies that would best distinguish between the two compounds shown. Specify which compound (A or B) will display a band at this frequency in its IR spectrum. Bond O-H (alcohol) O-H (carboxylic acid) N-H Stretching frequency (cm-¹) 3200-3650 2500-3300 3100-3550 2850-3000 3000-3100 C-H (alkane) C-H (alkene) C-H (alkyne) C=C 2100-2250 C=C 1600-1680 C=O (aldehyde/ketone) 1630-1820 C=O (ester) 1735-1800 1700-1725 C=O (carboxylic acid) C-O 1000-1250 A 3300 B OH Intensity Medium, broad Strong, broad Medium Medium Medium to strong Weak to medium Weak Weak to medium Strong Strong Strong Strong (Choose the most prominent frequency. Do not include units in your answer. Use only the frequencies listed above. If there is more than one correct answer, only give one.) Write the letter of the compound, followed by the range of frequencies, separated by a comma. Example. "A,1600-1850". IR frequency or range of frequencies: cm-1 Previous Nextarrow_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forward
- Predict (draw) the ¹H NMR and 13C NMR spectra for each molecule. Your illustration should include chemical shift, integration, and splitting (where appropriate). Label each signal in your spectrum a, b, c... etc and label the corresponding C/H atoms in each molecule. CIarrow_forwardIn the attached H1-NMR, draw and identify each set of equivalent hydrogens in the structure and list peak they belong to in the NMR spectrum.arrow_forwardQUESTION 1 The IR spectrum below belongs to an organic compound A having one nitrogen atom. Determine which structures that fits to the IR spectrum. Justify your answer by providing two (2) IR absorption peaks with their wavenumber. CN `NH2 Ahserbance /% 50- 100- 2000 Wavenumberrs/ cm 4000 3000 2F00 1F00 1000 F00arrow_forward
- Identify all of the peaks in the spectrum. State the Experimental wavelength, Literature wavelength, peak characteristic, and assignment. DOWN BELOW IS AN EXAMPLE... Experimental Wavelength (cm-1) Literature wavelength (cm-1) Peak characteristic assignment 3001cm-1, 3043cm-1 3010cm-1 sp2 C-H stretching alkene 2924cm-1 2900 -2980cm-1 sp3 C-H stretching Alkyl C-H 1614cm-1 1500 -1650cm-1 C=C stretch alkene 1443cm-1 1350-1450cm-1 C-H bend C-Harrow_forwardCH3 2. An unknown isomer of C4H9Cl has the ¹³C NMR and DEPT-135 spectra shown below: 13C NMR: 90 70 |||| A 50 8 (ppm) CH3CH₂CH₂ CH₂ CI 30 10 DEPT-135: CH3 CH3-CHCH₂-CI B 90 70 Circle the compound that is represented by these spectra. Clearly explain your reasoning. you will need to explain how each of the other three isomers was eliminated from consideration. 50 8 (ppm) CH3CH₂ CH-CI CH3 C 30 10 CH3 CH3-C-CI CH3 Darrow_forward2) For each of the following pairs of compounds, name one absorption band that can be used to distinguish between them. State what the bond is (bond order, between which 2 atoms), and approximately where it appears in the IR spectrum (in cm ¹). b) HO 1-hexanol OH phenol H₂N 1-butanamine ethyl acetate cyclohexane OH hexanoic acid LOH cyclohexanol NH₂ butanamide diethyl ether cyclohexenearrow_forward
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