Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 13, Problem 13.20P
Interpretation Introduction
Interpretation: The possible structure for
Concept Introduction: IR spectroscopy is used to identify the
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2.
Describe some of the vibrational mode at stretching and bending
associated with Infrared Spectroscopy. Draw representative structure
denoting such vibrational modes.
How does NMR spectroscopy provide information about chemical structure?
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Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 13 - What molecular ions would you expect for the...Ch. 13 - The mass spectrum of 2,3-dimethylpentane also...Ch. 13 - The base peak in the mass spectrum of 2, 2,...Ch. 13 - (a) What mass spectral fragments are formed by ...Ch. 13 - What cations are formed in the mass spectrometer...Ch. 13 - The low-resolution mass spectrum of an unknown...Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...
Ch. 13 - Prob. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - How do the three isomers of molecular formula...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Prob. 13.20PCh. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - What molecular ion is expected for each compound?Ch. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Match each structure to its mass spectrum. a. b....Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.32PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - Can the exact mass obtained in a high-resolution...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - Which of the highlighted bonds absorbs at higher v...Ch. 13 - What major IR absorptions are present above...Ch. 13 - How would each of the following pairs of compounds...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - Prob. 13.42PCh. 13 - 13.47 Match each compound to its IR spectrum
Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.49PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.52PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.56PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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- Following is the mass spectrum of bromocyclopentane. The molecular ion m/z 148 is of such low intensity that it does not appear in this spectrum. Assign structural formulas for the cations of m/z 69 and 41.arrow_forwardFollowing are infrared spectra of nonane and 1-hexanol. Assign each compound its correct spectrum.arrow_forwardThe proton NMR spectrum in Figure 19.39 is for an organic compound containing a single atom of bromine. Identify the compound.arrow_forward
- 1. Draw two constitutional isomers of the formula C6H11B1. Explain how you would differentiate those molecules using either spectroscopy or spectrometry. You only need to differentiate them using one example.arrow_forwarda) Shown below is the 1H NMR (CDCl3 is the solvent) of butanal. The splitting pattern of each of the four peaks is provided. For each of the four peaks determine the number of hydrogens that belongs to each peak from the red integral line. Provide the number of the hydrogens in the order A, B, C, D. b) What happens when the radiofrequncy pulse in the NMR instrument matches the Larmor Frequncy of an NMR active nucleus? A. The electrons transition to the LUMO B. The nuclei undergoes a spin flip C. Nothing D. The bonds in the molecule stretch and vibratearrow_forwardExplain the Effect of Resonance on IR Absorptions ?arrow_forward
- Counterfeit drugs are a common problem in developing regions of the world. Oftentimes, counterfeit pills are made with compounds such as lactose. A lab technician has obtained the IR spectrum shown above for a sample reported to be citalopram, an antidepressant drug. Does the IR spectrum belong to citalopram or lactose? Explain your answer by describing what feature of the IR spectrum confirms your choice and describe what feature is missing from the IR spectrum for the other compound. A. citalopram B. lactosearrow_forwardBy analyzing the COSY spectrum below, determine if it is the NMR spectrum of Compound A or Compound B. Explain how you reached your conclusion.arrow_forwardThe frequency of an absorption band in an IR spectrum depends primarily on: Type of vibration Masses of the atoms in a bond O Strength of the bond or bond order All answers correctarrow_forward
- Which of the following statements is incorrect regarding IR spectroscopy? options: The diagnostic region contain all signals that arise from double bonds, triple bonds and X-H bonds The fingerprint region contains signals resulting from the vibrational excitation of most single bonds (stretching and bending) The intensity of a signal is dependent on the dipole moment of bond giving rise to the signal A conjugated C=O bond produce a high energy signal than an unconjugated C=O bond The wavenumber of each signal is determined primarily by bond strength and the masses of the atoms sharing the bondsarrow_forwardHow many peaks would the 1H NMR spectrum of the following molecule have?arrow_forward(d) Indicate for three of the following pairs of compounds which spectroscopic method you would choose to distinguish between them [there may be more than one 'correct' technique]. Explain your choice and outline the differences you would expect to observe. OH DOH OH O OMe L MeO OMe, OH OH Pair D Pair E Pair F Pair G HO OMe ว MeO OMe, OH OHarrow_forward
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY