ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 13, Problem 13.44P
Morphine, heroin, and oxycodone are three addicting analgesic narcotics. How could IR spectroscopy be used to distinguish these three compounds from each other?
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Morphine, heroin, and oxycodone are three addicting analgesic narcotics. How could IR spectroscopy be used to distinguish these three compounds from each other?
The infrared spectrum of a compound is unique to the types and number of bonds in the molecule. Draw the structures of salicylic acid and aspirin. What are the key differences of the IR spectrum of aspirin with that of the starting material, salicylic acid? What are the similarities? Interpret the IR spectra of each by assigning the major peaks.
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.
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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 - Use the following information to propose a...Ch. 13 - Prob. 13.4PCh. 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. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...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 - Problem-13.21 Which of the following possible...Ch. 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 - Prob. 13.25PCh. 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 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum
Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...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 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 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. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 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. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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- what do the peaks in a IR spectrum represent?arrow_forwardApplications of NMR spectroscopy in pharmaceutical analysis Can potentially be used for fingerprinting mixtures Has good potential for non-destructive quantitative analysis of drugs in formulations without prior separation Can determine impurities, including enantiomeric impurities, without separation Powerfull technique for the characterization og the exact structure of raw materials, intermediates, and finished productsarrow_forward1. 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_forward
- how molecular spectroscopy work?arrow_forwardDefine Nuclear magnetic resonance (NMR) spectroscopy.arrow_forwardWhat is the meaning of the term wavenumber, which is used in IR spectroscopy? OIt is the total number of wavelengths of IR radiation absorbed by the compound. It is the number of waves that pass through a particular point each second. It is another term for the energy of radiation. OIt is how many waves the IR light contains.arrow_forward
- What is molecular spectroscopy and UV-VIS absorption, IR absorption spectroscopy and fluorescence spectroscopy?arrow_forwardPredict what a graph of absorbance versus concentration would look like. Sketch your prediction.arrow_forward1. Which of the following compounds absorb at higher wavelength, why? or orarrow_forward
- 2. You have two solutions of the same compound that are blue. One is very pale and the other is very intense. Absorbance of each solution was measured with a spectrophotometer at the same wavelength at which the solution absorbs. a) Which solution has the higher absorbance? b) Which is the more concentrated solution?arrow_forwardHow do the three isomers of molecular formula C3H6O (A, B, and C) differ in their IR spectra?arrow_forward1. TRUE OR FALSE a) Organic compounds are normally analyzed in atomic spectroscopy despite their small electronic transition range. b) Atomic spectroscopy can detect both absorption and emission radiation as electrons move from HOMO to LUMO.arrow_forward
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