ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 21.4A, Problem 21.2P
Interpretation Introduction
Interpretation: The characteristics of methyl benzoate spectrum that rule out an
Concept introduction: A method by which structure of compound is determined by the interaction between matter and
To determine: The characteristics of methyl benzoate spectrum that rule out an aldehyde or carboxylic acid functional group by giving absorption at
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The 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?
What characteristics of the methyl benzoate spectrum rule out an aldehyde or carboxylicacid functional group giving the absorption at 1723 cm-1?
The '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?
Chapter 21 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 21.2F - Name the following carboxylic acid derivatives,...Ch. 21.4A - Prob. 21.2PCh. 21.4A - Prob. 21.3PCh. 21.4A - Prob. 21.4PCh. 21.5C - Prob. 21.7PCh. 21.6 - When ethyl 4-hydroxybutyrate is heated in the...Ch. 21.6 - Propose a mechanism for the following ring-opening...Ch. 21.6 - Prob. 21.15PCh. 21.7B - Prob. 21.16PCh. 21.7C - Prob. 21.19P
Ch. 21.7C - Prob. 21.20PCh. 21.7C - Prob. 21.21PCh. 21.7D - Prob. 21.22PCh. 21.7D - The mechanism for acidic hydrolysis of a nitrile...Ch. 21.8A - Prob. 21.24PCh. 21.8C - Prob. 21.25PCh. 21.9 - Prob. 21.26PCh. 21.9 - Prob. 21.27PCh. 21.9 - Prob. 21.28PCh. 21.10 - Draw a mechanism for the acylation of anisole by...Ch. 21.10 - Prob. 21.30PCh. 21.11 - Prob. 21.31PCh. 21.11 - Prob. 21.32PCh. 21.12 - Problem 21-33 Propose a mechanism for the...Ch. 21.12 - Suggest the most appropriate reagent for each...Ch. 21.12 - Show how you would synthesize each compound,...Ch. 21.13 - Prob. 21.36PCh. 21.13 - Prob. 21.37PCh. 21.14 - Prob. 21.38PCh. 21.14 - Prob. 21.39PCh. 21.16 - Prob. 21.40PCh. 21.16 - Prob. 21.41PCh. 21 - Prob. 21.42SPCh. 21 - Give appropriate names for the following...Ch. 21 - Predict the major products formed when benzoyl...Ch. 21 - Predict the products of the following reactions....Ch. 21 - Prob. 21.46SPCh. 21 - Prob. 21.47SPCh. 21 - Prob. 21.48SPCh. 21 - Propose mechanisms for the following reactions.Ch. 21 - Prob. 21.51SPCh. 21 - An ether extraction of nutmeg gives large...Ch. 21 - Prob. 21.53SPCh. 21 - Show how you would accomplish the following...Ch. 21 - Prob. 21.55SPCh. 21 - Prob. 21.56SPCh. 21 - Prob. 21.57SPCh. 21 - Prob. 21.58SPCh. 21 - Prob. 21.59SPCh. 21 - Explain this curious result. What does this...Ch. 21 - Prob. 21.61SPCh. 21 - Prob. 21.62SPCh. 21 - Prob. 21.63SPCh. 21 - A chemist was called to an abandoned aspirin...Ch. 21 - Prob. 21.67SPCh. 21 - The IR spectrum, 13ONTVTR spectrum, and 1HNMR...Ch. 21 - Prob. 21.69SPCh. 21 - Prob. 21.70SPCh. 21 - Prob. 21.71SP
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- The 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_forwardWhy 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.arrow_forwardDraw the structural formulas of the following compounds and indicate the number of NMR signals that would be expected for each compound. (a) methyl iodide (b) 2,4-dimethylpentane (c) cyclopentane (d) propylene (propene)arrow_forward
- The line of integration of the two signals in the 1H-NMR spectrum of a ketone with the molecular formula C7H14O rises 62 and 10 chart divisions, respectively. Calculate the number of hydrogens giving rise to each signal and propose a structural formula for this ketone.arrow_forwardWhen the 1î-NMR spectrum of acetone, CH3COCH3, is recorded on an instrument operating at 200 MHz, a single sharp resonance at 2.1î is seen. (a) How many hertz downfield from TMS does the acetone resonance correspond to? (b) If the 1î-NMR spectrum of acetone were recorded at 500 MHz, what would the position of the absorption be in î units? (c) How many hertz downfield from TMS does this 500 MHz resonance correspond to?arrow_forwardWhich of the following compounds of molecular formula C6H1002, shows two singlets in its' H-NMR with areas of 2: 3, where the signal that integrates by 2 has a greater chemical shift?arrow_forward
- (a) What would be the chemical shift of a peak that is observed at 655.2 Hz from the reference tetramethylsilane (TMS) recorded using a 90 MHz spectrometer ? (b) At what frequency would the chemical shift of chloroform (CHCl3, δ = 7.28 ppm) occur relative to TMS on a spectrum recorded on a 300 MHz spectrometer? (c) At what frequency and chemical shift would the signal for chloroform occur when using a 1 GHz NMR spectrometer?arrow_forwardWhat would be the frequency of the fundamental absorption of a hydroxyl group if its first overtone was observed at 6200 cm³¹? What is the energy possessed by a band that appeared at 1710 cm¹ in an IR spectrum?arrow_forwardIdentify and explain the IR absorption characteristics of the unknown C6H14O in the 1400 to 4000 cm-1 range. Then identify the class of the unknown compound C6H14O. At the broad peak I believe it is either an alcohol & phenol or an amine. For the second peak i think it is an alkane.arrow_forward
- You have an unknown with an absorption at 1680 cm-1; it might be an amide, an isolated double bond, a conjugated ketone, aconjugated aldehyde, or a conjugated carboxylic acid. Describe what spectral characteristics you would look for to help youdetermine which of these possible functional groups might be causing the 1680 peak.arrow_forwardHow many signals in 1H NMR spectrum of methyl 3-nitrobenzoate? Identify their chemical shifts and the multiplicity.arrow_forwardThe 1H NMR spectrum of methylbenzene (C6H5CH3) recorded on a 500 Mhz spectrometer consists of signals at chemical shifts of 2.21 parts per million and 7.10 ppm. calculate the frequency, downfield of TMS, of each absorption.arrow_forward
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