ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 13, Problem 13.24P
The mass spectrum of the following compound shows fragments at
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The 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.
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 Intensity
A compound used as a moth repellant has three molecular ion peaks at m/z = 146 (100%), 148 (65%) & 150 (10%) amu in its mass spectrum. A pair of smaller peaks are seen at m/z= 111 (34%) & 113 (11%). The infrared spectrum shows sharp absorption just above 3000 cm^-1 region, and also at 1480 cm^-1. The ^1 H nmr shows a single sharp signal at delta = 7.2 ppm, and the ^13 C nmr has two signals (delta = 133 & 130 ppm).
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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- Write molecular formulas for compounds that show the following molecular ions in their high-resolution mass spectra, assuming that C, H, N, and O might be present. The exact atomic masses are: 1.007 83 (1H), 12.000 00 (12C), 14.003 07 (14N), 15.994 91 (16O). (a) M+=98.0844 (b) M+=123.0320arrow_forwardFollowing 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 3-methyl-2-butanol. The molecular ion m/z 88 does not appear in this spectrum. Propose structural formulas for the cations of m/z 45, 43, and 41.arrow_forward
- Following 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_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_forwardThe mass spectrum of an aldehyde shows a parent peak at m/z = 58 and a base peak at m/z = 29. Propose a structure, and identify the two species whose m/z values were listed. Name the compound in the box below.arrow_forward
- A mass peak at m/z = 59 appears in the mass spectrum of an amide, C5H11NO. Draw the structure of a molecule that is consistent with this result.arrow_forward5. The mass spectrum of an unknown compound shows a molecular ion peak at m/z 119, with a relative intensity of 39. The M + 1 peak has a relative intensity of 1 and the M + 2 peak has a relative intensity of 38. A major IR stretch for the compound is observed at 2253 cm³¹. Additionally, the following ratio of elements was observed following elemental analysis: 20.03% C, 1.68% H, and 11.68% N. Provide a reasonable molecular formula and a structure for the unknown.arrow_forwardPropose 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 peakarrow_forward
- 7arrow_forwardA mass spectrum shows significant peaks at m/z = 87, 115, 140, and 143. Which of the following compounds is responsible for that mass spectrum?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_forward
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