Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 13, Problem 13.30P
Propose a molecular formula for rose oxide, a rose-scented compound isolated from roses and geraniums, which contains the elements of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Use the following information to propose a molecular formula for nootkatone, a compound partly responsible for the characteristic odor of grapefruit. Nootkatone contains the elements C, H, and O, has ve degrees of unsaturation, and a molecular ion in its mass spectrum at m/z = 218.
The molecular ion peak in a mass spectrum of compound W appears at m/z = 107. Predict the molecular
formula of compound W. (Hint: Compound W contains a heteroatom, not only carbon and hydrogen).
Propose a molecular formula for a compound that exhibits the following peaks in its mass spectrum
(M)+• at m/z = 96, relative height = 19.0% of base peak; (M+1)+• at m/z = 97, relative height = 1.5% of base peak
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...
Additional Science Textbook Solutions
Find more solutions based on key concepts
The active ingredient in Tylenol and a host of other over-the-counter pain relievers is acetaminophen (C8H9NO2)...
Chemistry: Atoms First
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
Determine the de Brogue wavelength of a. an electron moving at 1/10 the speed of light. b. a 400 g Frisbee movi...
Inorganic Chemistry
Give one example from main group chemistry that illustrates each of the following descriptions: (a) Covalent ne...
General Chemistry: Atoms First
What is the pH range for acidic solutions? For basic solutions?
EBK INTRODUCTION TO CHEMISTRY
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Following is the mass spectrum of an unknown compound. The two highest peaks are at m/z 120 and 122. Suggest a structure for this compound. (Data from http://webbook.nist.gov/chemistry/.)arrow_forwardFollowing 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_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forward
- Compound F, a hydrocarbon with M+=96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, whose 13C NMR spectral data are given below. Compound F Broadband-decoupled 13C NMR: 27.6, 29.3, 32.2, 132.4 DEPT-90: 132.4 DEPT-135: positive peak at 132.4 ; negative peaks at 27.6, 29.3, 32.2 Compound G Broadband-decoupled 13C NMR: 25.1, 27.7, 39.9, 56.0 DEPT-90: 56.0 DEPT-135: positive peak at 56.0 ; negative peaks at 25.1, 27.7, 39.9arrow_forward2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?arrow_forwardA compound has a molecular ion in its mass spectrum at m / z = 58, and a strong absorption band at its IR at 1720. What would be the structure?arrow_forward
- Propylbenzene, C6H5CH2CH2CH3, and isopropyl benzene, C6H5CH(CH3)2, are constitutional isomers with the molecular formula C9H12. One of these compounds shows prominent peaks in its mass spectrum at m/z 120 and 105. The other shows prominent peaks at m/z 120 and 91. Which compound has which spectrum?arrow_forwardPropose a reasonable molecular formula for a compound with a degree of unsaturation and that in its mass spectrum shows a signal for the molecular ion at m / z = 100arrow_forwardPropose a molecular formula for a compound that exhibits the following peaks in its mass spectrum Problem 1: (M)+• at m/z = 72, relative height = 38.3% of base peak; (M+1)+• at m/z = 73, relative height = 1.7% of base peakarrow_forward
- A compound contains only C, H and O. The mass spectrum shows peaks at m/z = 58 and 43. What is the structure of the compound?arrow_forward18. What fragments might you expect in the mass spectra of the following compounds? (a) ملة لة سلم (b) OH (c) Harrow_forwardPropose a molecular formula for a compound that exhibits the given peaks in its mass spectrum. Draw a possible structure. M*• at m/z = 136, relative height = 12.1% (M+1)*• at m/z = 137, relative height = 1.2%arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY