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 15.12YT
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Which compound gives a signal in the 1H-NMR spectrum with a larger chemical shift, furan or cyclopentadiene? Explain.
Identify the significant absorption peaks by labeling them right on the spectrumand includethe spectrum in your laboratory report. Absorption peaks corresponding to the followinggroups should be identified:
C—H (SP3)
C—H (SP2)
C—H (aldehyde)
O—H
C=O
C=C (aromatic)aromatic substitution pattern
C—OC—X (if applicable)
The base peak in the mass spectrum of an alkane, C7H16, appears at m/z =57. Draw a molecule that is consistent with these data.
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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- Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)arrow_forwardThe simulated APT spectrum of a compound with the molecular formula C6H12 is shown. Draw a structure that is consistent with this data.arrow_forwardIdentify the significant absorption peaks by labeling them right on the spectrumand includethe spectrum in your laboratory report. Absorption peaks corresponding to the followinggroups should be identified: C—H (SP3) C—H (SP2) C—H (aldehyde) O—H C=O C=C (aromatic)aromatic substitution pattern C—OC—X (if applicable)arrow_forward
- Identify the following spectra. Please find peaks are assigned on the spectrum (~5-6 peaks). Label the peaks on the spectrum and place the structure of the compound in the box on the lower left-hand corner of the spectrum (from the table below, no numbering scheme). You do not have to indicate the exact wavenumber of the peak.arrow_forwardHow many 13C peaks should be seen in the broad-band decoupled spectrum of the structure at the right?arrow_forwardThe 1H NMR spectrum of 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS.(a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forward
- Two bottles labelled cis-cyclohexandiol were found in a laboratory. Because of their differing melting points, the bottles clearly contained two different cis-cyclohexandiol isomers. To determine which isomer was in which bottle, the chemist decided to run ¹3C NMR spectra on a sample of each. The three possible products were as in the figure. (Figure 1) The two ¹³C NMR proton-decoupled spectra contained the following data: ● ● Figure HO spectrum of sample in bottle A: 20.20, 62.55 spectrum of sample in bottle B: 16.09, 29.52, 36.15, 63.08 OH OH OH 1 of 1 OH OH Part A Identify which isomer was present in the bottle A. OH HO OH OH OH OHarrow_forwardThe 1H NMR spectrum of 1,2-dimethoxyethane (CH3OCH2CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downeld from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forwardThe 'H NMR spectrum of 1,2-dimethoxyethane (CH;OCH,CH2OCH3) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?arrow_forward
- From the 13C spectrum of a compound, one can assign signals to specific carbon atoms of the compound and determine the number of protons on each of those carbon atoms. Such information in conjunction with the DEPT C-13 chart will allow the appearance of the corresponding DEPT spectrum of the compound to be predicted. There are five signals (I – V) in the 13C spectrum of compound A as shown below. At the exactly same location of each of these five signals, "a peak", "no peak", or "an inverted peak" may appear in the corresponding DEPT-135 spectrum. Predict the DEPT-135 spectrum of compound A by selecting the expected signal appearance at each of these five locations in the DEPT-135 spectrum. - II II IV V in HO A 100 PPM 180 160 140 120 80 60 40 20 v At the location of signal I A. no peak v At the location of signal IIl В. а рeak v At the location of signal IIl C. an inverted peak v At the location of signal IV v A the location of signal Varrow_forwardPredict the number of signals expected (disregarding splitting) in the 1H spectrum of CH3-OCH2CH3arrow_forwardWhich of the following compounds (methylene blue, methyl orange, methyl red, or carotene) does the spectrum belong to?arrow_forward
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