Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 9, Problem 29P
In the mass spectrum of 2, 6-dimethyl-4-heptanol there are prominent peaks at m/z 87, 111, and 126. Propose reasonable structures for these fragment ions.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The mass spectrum of 3-ethyl-3-methylheptane [(CH3CH2)2C(CH3)CH2CH2CH2CH3] shows fragments at m/z = 127, 113, and 85. Propose structures for the ions that give rise to these peaks
The base peak in the mass spectrum of 2,2,5,5-tetramethylhexane (molecular mass = 142) is at m/z = 57, which corresponds to a composition of C4H9. Suggest a structure for the fragment that accounts for this peak and offer a reason for why this fragment is so abundant.
The mass spectrum of 2,2-dimethylpropane shows only a very weak molecular ion peak at m/z = 72. However, a large peak at m/z = 57 is seen. Suggest a possible structure of the fragment giving rise to this large peak and suggest a reason as to why this peak is so large.
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
Additional Science Textbook Solutions
Find more solutions based on key concepts
In qualitative analysis, Ca2+ and Ba2+ are separated from Na+, K+, and Mg2+ by adding aqueous (NH4)2CO3 to a so...
General Chemistry: Atoms First
For Practice 1.1
Is each change physical or chemical? Which kind of property (chemical or physical) is demonst...
Principles of Chemistry: A Molecular Approach (3rd Edition)
Propose an efficient synthesis for the following transformation:
Organic Chemistry As a Second Language: Second Semester Topics
The element with large atomic radius of the two unknown elements needs to be determined; if the atomic number o...
Chemistry: Matter and Change
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
- The mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forwardThe mass spectrum of 2,3-dimethylpentane also shows peaks at m/z = 57 and 43. Propose possible structures for the ions that give rise to these peaks.arrow_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_forward
- 1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).arrow_forwardThe mass spectrum of 2,3-dimethylpentane shows peaks at m/z = 57 and 43. Propose possible structures for the ions that give rise to these peaksarrow_forward2-Methylhexane shows an intense peak in the mass spectrum at m/z = 85, 57 and 43. Propose the possible structures for these fragments.arrow_forward
- Draw the structures of the fragments that give rise to the peaks at m/z 43, 57 and 85 in the mass spectrum of 2,4 - dimethylpentane. Thank you!arrow_forwardThe mass spectrum of the following compound shows fragments at m/z= 127, 113, and 85. Propose structures for the ions that give rise to thesepeaks.arrow_forwardThe molecular ion in the mass spectrum of 2-methyl-1-pentene appears at m/z 84. Propose structural formulas for the prominent peaks at m/z 69, 55, 41, and 29.arrow_forward
- The mass spectrum of 2,3-dimethylpentane also shows peaks at mlz = 57 and 43. Propose possible structures for the ions that give rise to these peaks.arrow_forwardThe mass spectrum of 1-propanol shows a large peak at m/z=31. Draw the structure of the fragment and explain why it is particularly stable.arrow_forwardAssigning Possible Structures to Fragments in a Mass Spectrum The mass spectrum of 2,3-dimethylpentane [(CH3)2CHCH(CH3)CH2CH3] shows fragments at m/z = 85 and 71. Propose possible structures for the ions that give rise to these peaks.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY