Concept explainers
Interpretation:
5-Cholestane-3-one is to be prepared from cholesterol. How IR spectroscopy could be used to predict whether the reaction was successful is to be stated. The differences that could be observed in the IR spectrum of the starting material and the product are to be given.
Concept introduction:
In IR, the alcohols have a strong C-O adsorption near 1050 cm-1 and a characteristic O-H stretching adsorption around 3300 to 3600cm-1. In hydrogen bonded alcohols this absorption occurs in the 3300cm-1 to 3400cm-1.
Aliphatic
To state:
The use of IR spectroscopy in predicting whether the reaction ‘Conversion of cholestane-3-one to cholesterol’ was successful or not.
To give:
The differences that could be observed in the IR spectrum of cholesterol and 5-cholestane-3-one.
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
Organic Chemistry
- Analyze the IR of acetone and 2-propanol. What are the most significant differences between these two spectra?arrow_forwardReduction of cyclohex-2-enone can yield cyclohexanone, cyclohex-2enol, or cyclohexanol, depending on the reagent and reaction conditions. How could you use IR spectroscopy to distinguish the three possible products?arrow_forwardCan you use IR spectroscopy to differentiate between ketones and aldehydes?arrow_forward
- An oxidation reaction was conducted using cyclohexanol and NaOCl to make cyclohexanone. How can we know that the NMR for cyclohexanone is in fact cyclohexanone( the NMR for cyclohexanone is not labeled). Analyze the spectra to prove its identity along with the NMR of the starting material which is the spectra labeled cyclohexanol below.arrow_forwardAcidified potassium dichromate(K2Cr2O7/H+) may be used to transform 3-methylpentanal into another compound via oxidation. How could you use IR Spectroscopy to distinguish between the reactant and the product?arrow_forwardWhat drastic change on the IR spectrum would you expect if you were to follow this reaction using IR spectroscopy? (5%) OH Mild oxidationarrow_forward
- Analyze the 1H NMR of 2-phenyl-2-propanol. Based on intensities and splitting patterns, it should be possible to assign all of the peaks in this spectrum. Analyze the 1H NMR of 2-cyclohexyl-2-propanol. In this case, it is not possible to assign all peaks. Indicate which peaks can be assigned to specific H atoms in this compound.arrow_forwardWhen 1-bromobutane is treated with sodium acetate(CH3CO2Na), the major product for the reaction is an ester (CH3CO2CH2CH2CH2CH3). Explain how mass spectrometry and IR spectroscopy could be used to prove that the reaction has occurred and you no longer have the starting material.arrow_forward1) The IR spectra for 4 "unknown" organic liquids are shown below. The identities of the liquids are: benzonitrile, butanoic acid, 2-pentanone, and 2-pentanol. Draw the structure of each possible unknown and match the unknown to its IR spectrum. Label the IR spectra with the bonds used for identification of structure. mummy M H W pumarrow_forward
- Take a look at the reaction in the first image that give two products A and B The second picture shows the DEPT 90 (TOP) and DEPT 135 (BOTTOM) of the compound that was isolated as only product of this reaction: In both spectra there are 7 signals between 120 and 140 ppm. How can you use these DEPT spectra to establish if product A or product B was formed in this reaction? Explain your reasoning.arrow_forwardDetermine the structure for the molecule that most likely produced these spectra.arrow_forwardBelow are three MS spectra, Spectra 1, 2, and 3. Each of this mass spectrum corresponds to either Compound A (contains one Cl in the molecular formula), Compound B (one I in the molecular formula), and Compound C (one Br in the molecular formula). Identify which spectra corresponds to which compound. Provide explanations for your choices.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY