Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 13, Problem 13.5P
The mass spectrum of 2, 3-dimethylpentane also shows peaks at
possible structures for the ions that give rise to these peaks.
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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.
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.
2,3-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?
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Prob. 13.3PCh. 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. 13.11PCh. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - How do the three isomers of molecular formula...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 - Prob. 13.20PCh. 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 - What molecular ion is expected for each compound?Ch. 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 - Match each structure to its mass spectrum. a. b....Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.32PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - Can the exact mass obtained in a high-resolution...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 - Which of the highlighted bonds absorbs at higher v...Ch. 13 - What major IR absorptions are present above...Ch. 13 - How would each of the following pairs of compounds...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - Prob. 13.42PCh. 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. 13.49PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.52PCh. 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. 13.56PCh. 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_forwardPropose structures for compounds that fit the following mass-spectral data: (a) A hydrocarbon with M+=132 (b) A hydrocarbon with M+=166 (c) A hydrocarbon with M+=84arrow_forward
- The mass spectrum (a) and the infrared spectrum (b) of an unknown hydrocarbon are shown. Propose as many structures as you can.arrow_forwardThe 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).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
- The 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_forwardThe mass spectrum of an alkene, C8H16, exhibits a peak at m/z = 41. Draw two isomers that are consistent with these data.arrow_forwardThe 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.arrow_forward
- A 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 spectra of two very stable cycloalkanes both show a molecular ion peak at m/z = 98 . One spectrum shows a base peak at m/z = 69, the other shows a base peak at m/z = 83. Identify the cycloalkane.arrow_forwardPls solve this problem and I upvote and pray for your wellbeingarrow_forward
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