ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
expand_more
expand_more
format_list_bulleted
Question
Chapter 9, Problem 30P
Interpretation Introduction
Interpretation:
The structure of the fragment ions of
Concept introduction:
Mass spectrometry is a technique used for measuring the masses of atoms and molecules with great accuracy.
In a mass spectrometer, the vapor of an organic compound is bombarded with a beam of high energy electrons that makes the neutral molecule loose an electron and get converted to a radical cation, known as molecular ion.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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).
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 CHEM. VOL.1+2-W/WILEYPLUS
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...
Knowledge Booster
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_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[References] The mass spectrum of octanoic acid, CH3(CH2)6COOH, exhibits a series of peaks differing by 14 amu at m/z 29, 43, 57, 71, 85, and 99. Draw the structure of the fragment resulting in the m/z 71 peak. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. • Do not use the square brackets tool in your answer. opy aste H,C earch 84%arrow_forward
- Th emajor fragmentation of the following molecule occurs through the Mclafferty rearrangement . which of the following is expected to be the base peak in the mass spectrum? I cleaved the compound on the bonds adjacent to the alpha and calculated the mass for the biggest fragment, which was m/z= 73. The answer is actually m/z = 86. Can someone give me a step by step on how to do this problem?arrow_forwardThe base peak in the mass spectrum of hexanamide appears at m/z = 59. Draw the ion that corresponds to this mass peak, and show how it is produced from the molecular ion.arrow_forwardBased on the mass spectrum shown below, 100 73 HO 80 A 58 20 100 10 20 30 40 50 100 60 70 m/z 80 90 110 (i) identify the molecular ion peak of compound A. (ii) explain how the labelled fragments are formed. Relative Intensityarrow_forward
- The mass spectrum of compound B is shown below. 100 180 80 181 77 В 182 20 104 25 50 75 100 125 150 175 200 m/z (i) Identify the molecular ion peak of compound B. (ii) Explain the peak at m/z 182 in terms of intensity. (iii) Explain the formation of the other labelled fragments (m/z 180, 104 and 77). Relative Intensityarrow_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
- Below is the mass spectrum of 2-methyl butane. Identify the base peak and molecular ion peak. Indicate the fragment that is lost to give rise to the peak at 57. relative abundance 29 afr 60 70 370237 mizarrow_forwardDraw the fragmentation arrow-pushing mechanisms to form the significant fragments of E-cinnamaldehyde (m/z 131, 103, 77, 51) (formed cations and radicals) based on the mass spectraarrow_forwardIn the mass spectra below, determine the Base Peak, the molecular ion peak and indicate the fragmentation process of ions marked with their respective value. 100 Mass Spectrum CH3 105 80 60 40 M 134 20 C3H100 40 80 120 160 200 240 280 m/e 100- 80 91 Mass Spectrum 60 134 40 20 149 C10 H15N 40 80 120 160 m/e 200 240 280 % of bese peak % of base peakarrow_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