ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
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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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. lactose
what do the peaks in a IR spectrum represent?
Applications 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 products
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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- 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_forwardhow molecular spectroscopy work?arrow_forwardHow does NMR spectroscopy provide information about chemical structure?arrow_forward
- 1. Which of the following compounds absorb at higher wavelength, why? or orarrow_forward2. 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_forwardWhy does Cytochrome C have a peak absorbance of 409nm? When proteins usually have a peak absorbance of 280nm..?arrow_forward
- Explain why these are the correct spectra for the molecules. Identify a specific absorption band which identifies each characteristic functional group of the molecule chosen.arrow_forwardWhat is the application of NMR in medical field? a. Imaging of organic molecules in soft tissues b. Antimicrobial detection c. Counting white blood cells d. Simultaneous quantitative measurementsarrow_forwardLook at the three infrared spectra in Figures C to D and answer the following questions (a) Are any of the spectra that of an alcohol? If so, which? What absorption pattern(s) at what wavelength(s) identifies an alcohol? (b) Are any of the spectra that of a compound containing a benzene ring? If so, which? What three absorption patterns at what wavelengths show that a compound has a benzene ring? (c) Are any of the spectra that of a compound containing only carbons and hydrogens? If so, which? Benzene rings contain only carbons and hydrogens. Might the spectrum or spectra you chose for your answer above indicate a benzene ring? (Tell what absorption patterns are present or not present that would support your answer.)arrow_forward
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